MiMeDB: Showing metabocard for Deoxycholic acid (MMDBc0000125)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:47 UTC

Update Date

2022-08-30 23:57:44 UTC

Metabolite ID

MMDBc0000125

Metabolite Identification

Common Name

Deoxycholic acid

Description

Deoxycholic acid is a secondary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH, and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). When present in sufficiently high levels, deoxycholic acid can act as a hepatotoxin, a metabotoxin, and an oncometabolite. A hepatotoxin causes damage to the liver or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. An oncometabolite is a compound, when present at chronically high levels, that promotes tumour growth and survival. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (PMID: 1641875 ). The liver toxicity of bile acids appears to be due to their ability to peroxidate lipids and to lyse liver cells. High bile acid levels lead to the generation of reactive oxygen species and reactive nitrogen species, disruption of the cell membrane and mitochondria, induction of DNA damage, mutation and apoptosis, and the development of reduced apoptosis capability upon chronic exposure (PMID: 24884764 ). Chronically high levels of deoxycholic acid are associated with familial hypercholanemia. In hypercholanemia, bile acids, including deoxycholic acid, are elevated in the blood. This disease causes liver damage, extensive itching, poor fat absorption, and can lead to rickets due to lack of calcium in bones. The deficiency of normal bile acids in the intestines results in a deficiency of vitamin K, which also adversely affects clotting of the blood. The bile acid ursodiol (ursodeoxycholic acid) can improve symptoms associated with familial hypercholanemia. Chronically high levels of deoxycholic acid are also associated with several forms of cancer including colon cancer, pancreatic cancer, esophageal cancer, and many other GI cancers.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

            
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627010001.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.412110001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.841010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555410001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.861710000.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.984510001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 27  1  6  0  0  0
 11  2  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  3  1  1  0  0  0
 13  4  1  1  0  0  0
 17  6  1  6  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  5  1  6  0  0  0
 20  8  1  1  0  0  0
 21 31  1  6  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22  1  1  1  0  0  0
 23  7  1  6  0  0  0
M  END

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

            
  Mrv1652305271900082D          

 33 36  0  0  0  0            999 V2000
10000.340010001.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0597 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2016 9999.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9142 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627010001.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3400 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6270 9999.7849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4883 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7738 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4883 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2001 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2001 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9147 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6292 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510000.6159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.913010000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9130 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6275 9998.9658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.126610000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.342010000.2032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3420 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.1266 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6115 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.126610001.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.412110001.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.841010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.555410001.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.861710000.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10003.270010002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.984510001.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 27  1  6  0  0  0
 11  2  1  6  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14  3  1  1  0  0  0
 13  4  1  1  0  0  0
 17  6  1  6  0  0  0
 19 13  1  0  0  0  0
 16 20  1  0  0  0  0
 19  5  1  6  0  0  0
 20  8  1  1  0  0  0
 21 31  1  6  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22  1  1  1  0  0  0
 23  7  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000125

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

> <INCHI_KEY>
KXGVEGMKQFWNSR-LLQZFEROSA-N

> <FORMULA>
C24H40O4

> <MOLECULAR_WEIGHT>
392.572

> <EXACT_MASS>
392.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
46.30045298852684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.7912592536666683

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396318179

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.651656794864149

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3511899140388809

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
109.19679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8667.3018668.598   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8659.3118662.405   0.000  0.00  0.00           O+0
HETATM    3  H   UNK     0    8663.3108661.633   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0    8663.3108666.265   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8664.6408663.961   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0    8665.9708669.038   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0    8667.3018663.961   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8665.9708666.265   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.9788665.489   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6448664.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6448663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9788662.409   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3078664.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3078663.179   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6418662.409   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.9758663.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.9718667.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.6388667.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6388665.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.9718664.736   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.7708667.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3058667.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3058665.506   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.7708665.030   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.6758666.276   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8668.7708669.062   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8667.4368669.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8670.1038669.832   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8671.4378669.062   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.7718669.832   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0    8670.1428668.221   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0    8672.7718671.372   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0    8674.1048669.062   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   13                                                            
CONECT    5   19                                                            
CONECT    6   17                                                            
CONECT    7   23                                                            
CONECT    8   20                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    4   19                                             
CONECT   14   13   15   12    3                                             
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17   18    6   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   13    5                                             
CONECT   20   19   16    8   23                                             
CONECT   21   22   25   26   31                                             
CONECT   22   21   23   17    1                                             
CONECT   23   22   24   20    7                                             
CONECT   24   23   25                                                       
CONECT   25   21   24                                                       
CONECT   26   21   28   27                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   32   33                                                  
CONECT   31   21                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000626
HETATM    1  C1  UNL     1      -4.494   0.548   1.956  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.526   0.575   0.756  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.336   0.274  -0.442  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.415   1.377  -0.514  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.287   1.185  -1.671  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.105   0.221  -2.447  1.00  0.00           O  
HETATM    7  O2  UNL     1      -7.324   2.062  -1.925  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.351  -0.216   1.069  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.508  -1.666   1.390  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.116  -2.290   1.173  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.265  -1.102   0.881  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.033  -1.321   0.231  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.976  -2.025   1.188  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.187  -1.243   1.547  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.931  -0.664   0.375  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.638   0.592   0.904  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.561   1.192  -0.102  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.676   2.584   0.046  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.991   0.946  -1.491  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.487   1.076  -1.381  1.00  0.00           C  
HETATM   21  C18 UNL     1       2.963  -0.163  -0.699  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.835  -1.231  -1.789  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.659   0.062   0.001  1.00  0.00           C  
HETATM   24  C21 UNL     1       0.753   0.938  -0.825  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.620   1.052  -0.228  1.00  0.00           C  
HETATM   26  O4  UNL     1      -0.535   1.743   0.982  1.00  0.00           O  
HETATM   27  C23 UNL     1      -1.241  -0.270   0.036  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.632  -0.990  -1.204  1.00  0.00           C  
HETATM   29  H1  UNL     1      -3.950   0.161   2.855  1.00  0.00           H  
HETATM   30  H2  UNL     1      -5.288  -0.207   1.734  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.908   1.540   2.174  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.216   1.661   0.697  1.00  0.00           H  
HETATM   33  H5  UNL     1      -4.873  -0.672  -0.317  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.813   0.385  -1.415  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.875   2.336  -0.639  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.971   1.362   0.442  1.00  0.00           H  
HETATM   37  H9  UNL     1      -8.283   1.915  -1.621  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.851   0.238   1.981  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.275  -2.180   0.811  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.745  -1.797   2.466  1.00  0.00           H  
HETATM   41  H13 UNL     1      -0.744  -2.766   2.096  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.140  -3.045   0.379  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.092  -0.542   1.823  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.026  -1.829  -0.752  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.435  -2.267   2.126  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.288  -3.029   0.775  1.00  0.00           H  
HETATM   47  H19 UNL     1       2.964  -0.489   2.340  1.00  0.00           H  
HETATM   48  H20 UNL     1       3.899  -1.963   2.041  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.623  -1.365  -0.090  1.00  0.00           H  
HETATM   50  H22 UNL     1       5.205   0.304   1.802  1.00  0.00           H  
HETATM   51  H23 UNL     1       3.835   1.316   1.146  1.00  0.00           H  
HETATM   52  H24 UNL     1       6.562   0.771   0.021  1.00  0.00           H  
HETATM   53  H25 UNL     1       6.125   2.907  -0.791  1.00  0.00           H  
HETATM   54  H26 UNL     1       5.406   1.653  -2.239  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.309  -0.071  -1.778  1.00  0.00           H  
HETATM   56  H28 UNL     1       3.240   2.002  -0.835  1.00  0.00           H  
HETATM   57  H29 UNL     1       3.078   1.130  -2.421  1.00  0.00           H  
HETATM   58  H30 UNL     1       1.934  -1.053  -2.403  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.701  -1.095  -2.499  1.00  0.00           H  
HETATM   60  H32 UNL     1       2.918  -2.244  -1.402  1.00  0.00           H  
HETATM   61  H33 UNL     1       1.799   0.507   0.997  1.00  0.00           H  
HETATM   62  H34 UNL     1       1.198   1.954  -0.817  1.00  0.00           H  
HETATM   63  H35 UNL     1       0.746   0.601  -1.869  1.00  0.00           H  
HETATM   64  H36 UNL     1      -1.224   1.674  -0.927  1.00  0.00           H  
HETATM   65  H37 UNL     1      -0.925   2.643   0.908  1.00  0.00           H  
HETATM   66  H38 UNL     1      -1.653  -0.340  -2.077  1.00  0.00           H  
HETATM   67  H39 UNL     1      -0.839  -1.760  -1.435  1.00  0.00           H  
HETATM   68  H40 UNL     1      -2.561  -1.591  -1.104  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    6    7
CONECT    7   37
CONECT    8    9   27   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   27   43
CONECT   12   13   23   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   21   49
CONECT   16   17   50   51
CONECT   17   18   19   52
CONECT   18   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   22   23
CONECT   22   58   59   60
CONECT   23   24   61
CONECT   24   25   62   63
CONECT   25   26   27   64
CONECT   26   65
CONECT   27   28
CONECT   28   66   67   68
END

HMDB0000626
     RDKit          3D
Deoxycholic acid
 68 71  0  0  0  0  0  0  0  0999 V2000
   -4.4938    0.5484    1.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5255    0.5752    0.7560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3363    0.2742   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4148    1.3774   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871    1.1848   -1.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1053    0.2213   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3240    2.0618   -1.9254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -0.2157    1.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5084   -1.6665    1.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -2.2898    1.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -1.1021    0.8808 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0333   -1.3209    0.2306 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -2.0248    1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1870   -1.2434    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309   -0.6645    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6375    0.5921    0.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    1.1916   -0.1020 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6763    2.5841    0.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    0.9456   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    1.0759   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628   -0.1633   -0.6991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8350   -1.2306   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    0.0622    0.0006 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7533    0.9375   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199    1.0519   -0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5349    1.7428    0.9820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.2698    0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6321   -0.9905   -1.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    0.1606    2.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2877   -0.2070    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    1.5402    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160    1.6607    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -0.6719   -0.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8132    0.3855   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.3363   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9707    1.3617    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2827    1.9146   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8511    0.2383    1.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2751   -2.1804    0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7453   -1.7972    2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438   -2.7657    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -3.0447    0.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0918   -0.5424    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -1.8292   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4352   -2.2674    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2884   -3.0287    0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -0.4895    2.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8993   -1.9626    2.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225   -1.3655   -0.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.3044    1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8349    1.3163    1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    0.7712    0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1245    2.9068   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4065    1.6526   -2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -0.0711   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2403    2.0021   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784    1.1298   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -1.0530   -2.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7014   -1.0955   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9179   -2.2439   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992    0.5070    0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    1.9545   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.6012   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    1.6743   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9252    2.6433    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.3403   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.7599   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5614   -1.5907   -1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  6
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  0
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  1
 24 62  1  0
 24 63  1  0
 25 64  1  6
 26 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
M  END

Synonyms

Value	Source
(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID	ChEBI
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid	ChEBI
3alpha,12alpha-Dihydroxy-5beta-cholanic acid	ChEBI
7alpha-Deoxycholic acid	ChEBI
Desoxycholic acid	ChEBI
Desoxycholsaeure	ChEBI
Deoxycholate	Kegg
3alpha,12alpha-Dihydroxy-5beta-cholanate	Kegg
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid	Generator
(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5α,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oate	Generator
(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid	Generator
(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oate	Generator
(3Α,5β,12α)-3,12-dihydroxycholan-24-Oic acid	Generator
3a,12a-Dihydroxy-5b-cholanate	Generator
3a,12a-Dihydroxy-5b-cholanic acid	Generator
3Α,12α-dihydroxy-5β-cholanate	Generator
3Α,12α-dihydroxy-5β-cholanic acid	Generator
7a-Deoxycholate	Generator
7a-Deoxycholic acid	Generator
7alpha-Deoxycholate	Generator
7Α-deoxycholate	Generator
7Α-deoxycholic acid	Generator
Desoxycholate	Generator
5b-Cholanic acid-3a,12a-diol	HMDB
5b-Deoxycholate	HMDB
5b-Deoxycholic acid	HMDB
7-Deoxycholate	HMDB
7-Deoxycholic acid	HMDB
Cholerebic	HMDB
Cholorebic	HMDB
Degalol	HMDB
Deoxy-cholate	HMDB
Deoxy-cholic acid	HMDB
Deoxycholatate	HMDB
Deoxycholatic acid	HMDB
Acid, lagodeoxycholic	HMDB
Deoxycholic acid, 5alpha isomer	HMDB
Deoxycholic acid, sodium salt, 12beta-isomer	HMDB
Lagodeoxycholic acid	HMDB
Acid, choleic	HMDB
Deoxycholic acid, 12beta isomer	HMDB
Deoxycholic acid, 3beta-isomer	HMDB
Deoxycholic acid, monoammonium salt	HMDB
12beta-Isomer deoxycholic acid	HMDB
3beta-Isomer deoxycholic acid	HMDB
Acid, 5alpha-isomer deoxycholic	HMDB
Acid, deoxycholic	HMDB
Acid, desoxycholic	HMDB
Deoxycholate, sodium	HMDB
Deoxycholic acid, 12beta-isomer	HMDB
Deoxycholic acid, 5alpha-isomer	HMDB
Deoxycholic acid, monopotassium salt	HMDB
Deoxycholic acid, monosodium salt	HMDB
5alpha-Isomer deoxycholic acid	HMDB
Acid, dihydroxycholanoic	HMDB
Choleic acid	HMDB
Deoxycholic acid, 3beta isomer	HMDB
Deoxycholic acid, disodium salt	HMDB
Deoxycholic acid, magnesium (2:1) salt	HMDB
Dihydroxycholanoic acid	HMDB
Sodium deoxycholate	HMDB

Molecular Formula

C₂₄H₄₀O₄

Average Mass

392.572

Monoisotopic Mass

392.292659768

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

CAS Registry Number

83-44-3

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1

InChI Key

KXGVEGMKQFWNSR-LLQZFEROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Dihydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
3-alpha-hydroxysteroid
12-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid (CHEBI:28834 )
dihydroxy-5beta-cholanic acid (CHEBI:28834 )
C24 bile acids, alcohols, and derivatives (C04483 )
Cholane and derivatives (C04483 )
C24 bile acids, alcohols, and derivatives (LMST04010040 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.3	ALOGPS
logP	3.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	46.3 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00os-0119000000-ff101495d4bc6a37fc83	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-1110390000-cc7d539ad02f4039ec09	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0009000000-8b9c4803e9cb1d194c2e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-0009000000-cccabd9d13ac783b6e31	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0007-2009000000-d7c20760d2074c07af22	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-0009000000-269a5d1ed75b71c78ecb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0007-0009000000-72f1acf9f31f344daaa1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-000x-0008000900-ebb0e6a61bd8f06a21f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0009000000-8078ef73008efc65c713	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0009000000-269a5d1ed75b71c78ecb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-ade8ee412cabab0a5cdd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0007-0009000000-827a9ce119d7f2f1cb5c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-46347f9ccba012a193b3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0007-0009000000-7de3b9549dc580acb2af	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0007-0009000000-72f1acf9f31f344daaa1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0007-0009000000-fa7c4f74eaf1bb2e1f57	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-737c78b82fef7180b7ac	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-eb86d43bab0334d7cfe4	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0009000000-db8bf3905980e8620f12	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009000000-6a632f1c8fbb19a314cb	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-4219000000-29a9a2c5d3d148fca202	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-ab9ac299290313e78fe4	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1009000000-6444232cac6b7a24dd96	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-b2f4c82d34550211259c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-054o-0019000000-a4dfbb4ad2f96e8ee6db	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adl-4298000000-b6171657518bf9639cbe	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Erythrocyte
Feces
Fibroblasts
Intestine
Urine

Tissue Locations

Erythrocyte
Fibroblasts
Intestine

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192108	Solute carrier organic anion transporter family member 1B3	Transporter	Q9NPD5	Homo sapiens
MMDBp0192115	Solute carrier organic anion transporter family member 1B1	Transporter	Q9Y6L6	Homo sapiens
MMDBp0193395	Canalicular multispecific organic anion transporter 2	Transporter	O15438	Homo sapiens
MMDBp0193400	Bile salt export pump	Transporter	O95342	Homo sapiens
MMDBp0193547	Ileal sodium/bile acid cotransporter	Transporter	Q12908	Homo sapiens
MMDBp0193558	Bile acid receptor	Enzyme	Q96RI1	Homo sapiens
MMDBp0193577	Sodium/bile acid cotransporter	Transporter	Q14973	Homo sapiens
MMDBp0193639	Solute carrier organic anion transporter family member 1A2	Transporter	P46721	Homo sapiens
MMDBp0193865	Solute carrier organic anion transporter family member 4A1	Transporter	Q96BD0	Homo sapiens
MMDBp0195864	Gastrotropin	Unknown	P51161	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0004172	Cholic acid	Deoxycholic acid	Not Available	RE2112C	VMH	11344576 12393855
MMDBr0004173	Cholic acid	Deoxycholic acid	Cytochrome p450, family 7, subfamily a, polypeptide 1	RE2112R	VMH	11344576 12393855
MMDBr0004321	Adenosine triphosphate	Adenosine monophosphate	Not Available	Cholate- Coenzyme A Ligase	VMH	6639941
MMDBr0004322	Adenosine triphosphate	Adenosine monophosphate	Solute carrier family 27 (fatty acid transporter), member 5	Cholate- Coenzyme A Ligase	VMH	6639941
MMDBr0004323	Hydrogen Ion	Deoxycholic acid	Not Available	RE2636C	VMH	11980911
MMDBr0004324	Hydrogen Ion	Deoxycholic acid	Cytochrome p450, family 8, subfamily b, polypeptide 1	RE2636R	VMH	11980911
MMDBr0005793	Adenosine triphosphate	ADP	Atp-binding cassette, sub-family b (mdr/tap), member 11	Transport of Deoxycholate	VMH	30371894
MMDBr0005794	Deoxycholic acid	Deoxycholic acid	Not Available	Transport of Deoxycholate, Antiport with Bicarbonate	VMH	30371894
MMDBr0009600	Deoxycholic acid	Water	Not Available	Glycodeoxycholate Amidohydrolase	VMH	30371894
MMDBr0012380	Deoxycholic acid	Deoxycholic acid 3-glucuronide	Udp glucuronosyltransferase 2 family, polypeptide a1, complex locus	UDP-Glucuronosyltransferase (UGT) cytosolic (deoxycholic acid)	VMH	30371894
MMDBr0012381	Deoxycholic acid	Deoxycholic acid 3-glucuronide	Udp glucuronosyltransferase 2 family, polypeptide a1, complex locus	UDP-Glucuronosyltransferase (UGT) ER (deoxycholic acid)	VMH	30371894
MMDBr0012644	Deoxycholic acid	Deoxycholic acid	Not Available	Deoxycholate exporter	VMH	30371894
MMDBr0016280	Adenosine triphosphate	Adenosine monophosphate	Bile acid--coenzyme A ligase	Ligation; Synthesis	RHEA	34755880
MMDBr0016281	Adenosine triphosphate	Adenosine monophosphate	Bile acid--coenzyme A ligase	Ligation; Synthesis	RHEA	34755880
MMDBr0016294	Deoxycholic acid	12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016295	Deoxycholic acid	12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016296	Deoxycholic acid	12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016297	Deoxycholic acid	12alpha-hydroxy-3-oxo-5beta-cholan-24-oic acid	3alpha-hydroxysteroid dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0016330	glycodeoxycholic acid	Deoxycholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016331	glycodeoxycholic acid	Deoxycholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016332	Water	Deoxycholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016333	Water	Deoxycholic acid	Conjugated bile acid hydrolase	Hydrolysis of bond	RHEA	34755880
MMDBr0016447	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016448	Cholic acid	Choloyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016678	allocholic acid	allocholoyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016679	allocholic acid	allocholoyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016689	beta-muricholic acid	beta-muricholoyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016690	beta-muricholic acid	beta-muricholoyl-CoA	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016694	Deoxycholoyl Coenzyme A	Deoxycholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880
MMDBr0016695	Deoxycholoyl Coenzyme A	Deoxycholic acid	Bile acid CoA-transferase BaiF	Transfer of CoA moiety	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Cystic fibrosis	Slight Increase	Association	Human Blood	HMDB	15185309
Primary biliary cirrhosis		Association	Human Urine	HMDB	2621422

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	23	Human ; Human mucosa; Human feces; Human saliva; Human stool; Human urine; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	2	Human feces; Human stool; Human ; Human saliva	Microbial culture
Bacteria	Proteobacteria	1	Human ; Human feces	Microbial culture
Bacteria	Actinobacteria	9	Human ; Human feces; Human saliva; Human mucosa; Human vaginal fluid; Human stool	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.43	0.09			uM	Adult (>18 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Blood	Detected and Quantified	0.76	0.26			uM	Children (1-13 years old)	Both	Cystic fibrosis	HMDB	15185309
Human Urine	Detected and Quantified	0.3		0.06	0.87	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.328		0.0679	0.871	umol/mmol creatinine	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.5		0.1	1.3	umol/mmol creatinine	Adult (>18 years old)	Both	Biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.509		0.113	1.324	umol/mmol creatinine	Adult (>18 years old)	Both	Primary biliary cirrhosis	HMDB	2621422
Human Urine	Detected and Quantified	0.055		0.05	0.060	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Blood	Detected and Quantified	0.33	0.06			uM	Adult (>18 years old)	Both	Normal	HMDB	15185309
Human Bile	Detected and Quantified	11720		11570	11860	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Feces	Detected and Quantified	1920.10	1390.50			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.57	0.35			uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26476344
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000626

DrugBank ID

DB03619

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deoxycholic acid

METLIN ID

265

PubChem Compound

222528

PDB ID

Not Available

ChEBI ID

28834

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Andersen RB, Bruusgaard A: Effect of the common bile acids on the fibrin/fibrinogen fragments in rheumatoid synovial fluid. A possible clue to the ameliorating effect of jaundice in rheumatoid arthritis. Scand J Rheumatol. 1975;4(3):158-64. doi: 10.3109/03009747509165446. [PubMed:52191 ]
Deleze G, Paumgartner G, Karlaganis G, Giger W, Reinhard M, Sidiropoulos D: Bile acid pattern in human amniotic fluid. Eur J Clin Invest. 1978 Feb;8(1):41-5. doi: 10.1111/j.1365-2362.1978.tb00807.x. [PubMed:417931 ]
Delzenne NM, Calderon PB, Taper HS, Roberfroid MB: Comparative hepatotoxicity of cholic acid, deoxycholic acid and lithocholic acid in the rat: in vivo and in vitro studies. Toxicol Lett. 1992 Jul;61(2-3):291-304. doi: 10.1016/0378-4274(92)90156-e. [PubMed:1641875 ]
Berr F, Stellaard F, Pratschke E, Paumgartner G: Effects of cholecystectomy on the kinetics of primary and secondary bile acids. J Clin Invest. 1989 May;83(5):1541-50. doi: 10.1172/JCI114050. [PubMed:2708522 ]
Stadler J, Yeung KS, Furrer R, Marcon N, Himal HS, Bruce WR: Proliferative activity of rectal mucosa and soluble fecal bile acids in patients with normal colons and in patients with colonic polyps or cancer. Cancer Lett. 1988 Jan;38(3):315-20. doi: 10.1016/0304-3835(88)90023-7. [PubMed:3349450 ]
Yamaga N, Adachi K, Shimizu K, Miyake S, Sumi F, Miyagawa I, Goto H: Bile acids of patients with renal failure receiving chronic hemodialysis. Steroids. 1986 Nov-Dec;48(5-6):427-38. doi: 10.1016/0039-128x(86)90029-2. [PubMed:3445292 ]
Stellaard F, Paumgartner G, van Berge Henegouwen GP, van der Werf SD: Determination of deoxycholic acid pool size and input rate using [24-13C]deoxycholic acid and serum sampling. J Lipid Res. 1986 Nov;27(11):1222-5. [PubMed:3559388 ]
Beher WT, Gabbard A, Norum RA, Stradnieks S: Effect of blood high density lipoprotein cholesterol concentration on fecal steroid excretion in humans. Life Sci. 1983 Jun 27;32(26):2933-7. doi: 10.1016/0024-3205(83)90643-4. [PubMed:6865641 ]
Heikkinen J, Maentausta O, Tuimala R, Ylostalo P, Janne O: Amniotic fluid bile acids in normal and pathologic pregnancy. Obstet Gynecol. 1980 Jul;56(1):60-4. [PubMed:7383489 ]
Rudi J, Schonig T, Stremmel W: -Therapy with ursodeoxycholic acid in primary biliary cirrhosis in pregnancy-. Z Gastroenterol. 1996 Mar;34(3):188-91. [PubMed:8650973 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
Salen G, Tint GS, Eliav B, Deering N, Mosbach EH: Increased formation of ursodeoxycholic acid in patients treated with chenodeoxycholic acid. J Clin Invest. 1974 Feb;53(2):612-21. doi: 10.1172/JCI107596. [PubMed:11344576 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Costarelli V, Sanders TA: Plasma deoxycholic acid concentration is elevated in postmenopausal women with newly diagnosed breast cancer. Eur J Clin Nutr. 2002 Sep;56(9):925-7. doi: 10.1038/sj.ejcn.1601396. [PubMed:12209383 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
Nobuoka A, Takayama T, Miyanishi K, Sato T, Takanashi K, Hayashi T, Kukitsu T, Sato Y, Takahashi M, Okamoto T, Matsunaga T, Kato J, Oda M, Azuma T, Niitsu Y: Glutathione-S-transferase P1-1 protects aberrant crypt foci from apoptosis induced by deoxycholic acid. Gastroenterology. 2004 Aug;127(2):428-43. doi: 10.1053/j.gastro.2004.05.021. [PubMed:15300575 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Duret G, Delcour AH: Deoxycholic acid blocks vibrio cholerae OmpT but not OmpU porin. J Biol Chem. 2006 Jul 21;281(29):19899-905. doi: 10.1074/jbc.M602426200. Epub 2006 May 2. [PubMed:16670088 ]
Ajouz H, Mukherji D, Shamseddine A: Secondary bile acids: an underrecognized cause of colon cancer. World J Surg Oncol. 2014 May 24;12:164. doi: 10.1186/1477-7819-12-164. [PubMed:24884764 ]

Showing metabocard for Deoxycholic acid (MMDBc0000125)

MOL for #<Metabolite:0x00007fe2a490fd88>

3D MOL for #<Metabolite:0x00007fe2a490fd88>

3D SDF for #<Metabolite:0x00007fe2a490fd88>

3D-SDF for #<Metabolite:0x00007fe2a490fd88>

PDB for #<Metabolite:0x00007fe2a490fd88>

3D PDB for #<Metabolite:0x00007fe2a490fd88>

SMILES for #<Metabolite:0x00007fe2a490fd88>

INCHI for #<Metabolite:0x00007fe2a490fd88>

Structure for #<Metabolite:0x00007fe2a490fd88>

3D Structure for #<Metabolite:0x00007fe2a490fd88>