MiMeDB: Showing metabocard for 12-Ketodeoxycholic acid (MMDBc0031985)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:34 UTC

Update Date

2024-04-30 19:53:58 UTC

Metabolite ID

MMDBc0031985

Metabolite Identification

Common Name

12-Ketodeoxycholic acid

Description

NULL

Structure

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


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
   14.4630  -11.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7283  -14.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3413   -9.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6360  -10.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -13.5017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7486  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -12.2641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9979  -13.5074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9912  -14.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9580  -12.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4763  -14.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9580  -13.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486  -12.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7354  -14.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4395  -12.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -11.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2332  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2195  -14.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2144  -11.2287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -11.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0043  -12.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4513  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4444  -14.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0215  -11.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6634  -10.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2779  -10.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0852  -10.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0372  -13.8272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2473  -13.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3201  -12.7592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938  -15.0265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6101  -11.9105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 29  1  1  0  0  0
  6  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 31  1  6  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 10 32  1  1  0  0  0
 11 16  1  0  0  0  0
 11 20  1  0  0  0  0
 11 33  1  6  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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  2  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  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  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  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 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
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END


  Mrv0541 02231218272D          

 33 36  0  0  1  0            999 V2000
   14.4630  -11.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7283  -14.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3413   -9.3201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6360  -10.7182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -13.5017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7486  -13.0892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -12.2641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9979  -13.5074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.9912  -14.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9580  -12.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4763  -14.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9580  -13.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7486  -12.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7354  -14.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4395  -12.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4630  -11.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2332  -13.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2195  -14.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2144  -11.2287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1774  -11.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0043  -12.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4513  -13.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4444  -14.3725    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0215  -11.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6634  -10.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2779  -10.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0852  -10.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0372  -13.8272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2473  -13.7454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3201  -12.7592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9938  -15.0265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6101  -11.9105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
 24  2  1  6  0  0  0
  3 28  1  0  0  0  0
  4 28  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 29  1  1  0  0  0
  6  8  1  0  0  0  0
  6 13  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 31  1  6  0  0  0
  8 11  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  1  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
  9 22  1  1  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 10 32  1  1  0  0  0
 11 16  1  0  0  0  0
 11 20  1  0  0  0  0
 11 33  1  6  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 20 26  1  6  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031985

> <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])CC(=O)[C@]12C)[C@H](C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

> <INCHI_KEY>
CVNYHSDFZXHMMJ-VPUMZWJWSA-N

> <FORMULA>
C24H38O4

> <MOLECULAR_WEIGHT>
390.5561

> <EXACT_MASS>
390.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.515900800801035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
4.3547869593333335

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.296396219790154

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.556916959655809

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569565006749031

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
108.37449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ketolithocholic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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  2  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  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  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  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 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
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.998 -20.583   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      20.026 -27.593   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.237 -17.398   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.787 -20.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      26.998 -25.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.331 -24.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.664 -24.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.331 -22.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.263 -25.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.250 -26.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.788 -22.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.022 -26.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.788 -24.902   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.664 -22.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.639 -27.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.687 -23.663   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.998 -22.123   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.835 -24.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.810 -27.664   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.267 -20.960   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.331 -21.353   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.275 -23.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.376 -25.158   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.363 -26.829   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.773 -20.643   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.238 -19.814   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.252 -19.179   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      33.759 -18.861   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      28.069 -25.811   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      28.462 -25.658   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      26.731 -23.817   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      24.255 -28.049   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      31.006 -22.233   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   24                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    6    7   12   29                                             
CONECT    6    5    8   13   30                                             
CONECT    7    5    9   14   31                                             
CONECT    8    6   11   17   21                                             
CONECT    9    7   10   18   22                                             
CONECT   10    9   15   19   32                                             
CONECT   11    8   16   20   33                                             
CONECT   12    5   15                                                       
CONECT   13    6   16                                                       
CONECT   14    7   17                                                       
CONECT   15   10   12                                                       
CONECT   16   11   13                                                       
CONECT   17    1    8   14                                                  
CONECT   18    9   23                                                       
CONECT   19   10   24                                                       
CONECT   20   11   25   26                                                  
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   18   24                                                       
CONECT   24    2   19   23                                                  
CONECT   25   20   27                                                       
CONECT   26   20                                                            
CONECT   27   25   28                                                       
CONECT   28    3    4   27                                                  
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0000328
HETATM    1  C1  UNL     1       4.347   0.623   1.185  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.763  -0.668   0.735  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.219  -0.884  -0.706  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.768  -0.893  -0.638  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.261  -1.962   0.232  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.757  -3.119   0.061  1.00  0.00           O  
HETATM    7  O2  UNL     1       7.217  -1.809   1.211  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.331  -0.917   1.004  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.996  -0.877   2.475  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.764   0.055   2.564  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.102  -0.326   1.303  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.124   0.366   0.888  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.239  -0.094   1.845  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.580   0.410   1.483  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.921   0.450   0.037  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.674  -0.801  -0.428  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.411  -0.439  -1.719  1.00  0.00           C  
HETATM   18  O3  UNL     1      -5.468  -1.538  -2.561  1.00  0.00           O  
HETATM   19  C16 UNL     1      -4.638   0.654  -2.458  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.180   0.344  -2.298  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.748   0.675  -0.875  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.440   2.157  -0.852  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.572  -0.136  -0.464  1.00  0.00           C  
HETATM   24  C21 UNL     1      -0.482  -0.232  -1.486  1.00  0.00           C  
HETATM   25  C22 UNL     1       0.703  -0.868  -0.886  1.00  0.00           C  
HETATM   26  O4  UNL     1       1.193  -1.860  -1.306  1.00  0.00           O  
HETATM   27  C23 UNL     1       1.279  -0.183   0.321  1.00  0.00           C  
HETATM   28  C24 UNL     1       1.500   1.243  -0.056  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.434   0.469   1.508  1.00  0.00           H  
HETATM   30  H2  UNL     1       4.445   1.325   0.330  1.00  0.00           H  
HETATM   31  H3  UNL     1       3.870   1.149   2.001  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.340  -1.460   1.304  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.971  -0.037  -1.344  1.00  0.00           H  
HETATM   34  H6  UNL     1       3.957  -1.883  -1.091  1.00  0.00           H  
HETATM   35  H7  UNL     1       6.150  -1.098  -1.671  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.135   0.108  -0.364  1.00  0.00           H  
HETATM   37  H9  UNL     1       8.088  -1.372   1.006  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.148  -2.009   0.716  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.741  -0.459   3.131  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.661  -1.845   2.888  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.168  -0.186   3.460  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.080   1.102   2.583  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.139  -1.433   1.332  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.115   1.457   0.982  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.966   0.273   2.856  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.186  -1.214   1.876  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.330  -0.287   1.961  1.00  0.00           H  
HETATM   48  H20 UNL     1      -3.740   1.391   2.015  1.00  0.00           H  
HETATM   49  H21 UNL     1      -4.631   1.289  -0.117  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.995  -1.658  -0.588  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.441  -0.994   0.352  1.00  0.00           H  
HETATM   52  H24 UNL     1      -6.426  -0.052  -1.469  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.964  -1.414  -3.406  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.943   0.635  -3.537  1.00  0.00           H  
HETATM   55  H27 UNL     1      -4.889   1.650  -2.088  1.00  0.00           H  
HETATM   56  H28 UNL     1      -2.994  -0.736  -2.437  1.00  0.00           H  
HETATM   57  H29 UNL     1      -2.528   0.951  -2.950  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.540   2.603   0.147  1.00  0.00           H  
HETATM   59  H31 UNL     1      -3.172   2.719  -1.504  1.00  0.00           H  
HETATM   60  H32 UNL     1      -1.453   2.356  -1.264  1.00  0.00           H  
HETATM   61  H33 UNL     1      -1.925  -1.196  -0.300  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.245   0.741  -1.963  1.00  0.00           H  
HETATM   63  H35 UNL     1      -0.861  -0.897  -2.294  1.00  0.00           H  
HETATM   64  H36 UNL     1       0.534   1.821  -0.107  1.00  0.00           H  
HETATM   65  H37 UNL     1       1.873   1.264  -1.118  1.00  0.00           H  
HETATM   66  H38 UNL     1       2.163   1.835   0.550  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   26   27
CONECT   27   28
CONECT   28   64   65   66
END

HMDB0000328
     RDKit          3D
12-Ketodeoxycholic acid
 66 69  0  0  0  0  0  0  0  0999 V2000
    4.3475    0.6229    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -0.6680    0.7353 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2189   -0.8838   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -0.8934   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.9620    0.2324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7572   -3.1189    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2174   -1.8091    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306   -0.9169    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9960   -0.8769    2.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    0.0554    2.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.3265    1.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1238    0.3655    0.8882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2386   -0.0942    1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5800    0.4099    1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9210    0.4496    0.0375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6736   -0.8006   -0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4114   -0.4389   -1.7187 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4679   -1.5375   -2.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6381    0.6541   -2.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    0.3440   -2.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7483    0.6751   -0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4403    2.1569   -0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -0.1361   -0.4640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4823   -0.2322   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.8682   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1930   -1.8601   -1.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.1831    0.3209 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4999    1.2429   -0.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4335    0.4688    1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4450    1.3250    0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    1.1495    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402   -1.4603    1.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9714   -0.0373   -1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9569   -1.8828   -1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498   -1.0984   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1345    0.1083   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0885   -1.3717    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -2.0090    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7411   -0.4588    3.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -1.8454    2.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.1862    3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    1.1018    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -1.4329    1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.4570    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.2726    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1857   -1.2136    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -0.2874    1.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401    1.3913    2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.2886   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951   -1.6580   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -0.9945    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4262   -0.0517   -1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9641   -1.4141   -3.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9426    0.6346   -3.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8886    1.6503   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9943   -0.7361   -2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9513   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398    2.6031    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1716    2.7186   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4533    2.3562   -1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.1963   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2449    0.7409   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -0.8970   -2.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5344    1.8207   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    1.2645   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628    1.8348    0.5498 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  2  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  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  6
  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  1
 16 50  1  0
 16 51  1  0
 17 52  1  1
 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
 28 64  1  0
 28 65  1  0
 28 66  1  0
M  END

Synonyms

Value	Source
12-Ketodeoxycholate	Generator
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate	HMDB
(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid	HMDB
12-Dehydrodeoxycholate	HMDB
12-Dehydrodeoxycholic acid	HMDB
12-Ketolithocholate	HMDB
12-Ketolithocholic acid	HMDB
12-oxo-3a-Hydroxy-5b-cholanate	HMDB
12-oxo-3a-Hydroxy-5b-cholanic acid	HMDB
12-Oxolithocholate	HMDB
12-Oxolithocholic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oate	HMDB
3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanate	HMDB
3a-Hydroxy-12-oxo-5b-cholanic acid	HMDB
3a-Hydroxy-12-oxo-5b-cholanoate	HMDB
3a-Hydroxy-12-oxo-5b-cholanoic acid	HMDB
3-Hydroxy-12-ketocholanoic acid	HMDB
12-Ketolithocholic acid, (3beta,5beta)-isomer	HMDB
3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid	HMDB
(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate	HMDB

Molecular Formula

C₂₄H₃₈O₄

Average Mass

390.5561

Monoisotopic Mass

390.277009704

IUPAC Name

(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid

Traditional Name

12-ketolithocholic acid

CAS Registry Number

Not Available

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])CC(=O)[C@]12C)[C@H](C)CCC(O)=O

InChI Identifier

InChI=1S/C24H38O4/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/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1

InChI Key

CVNYHSDFZXHMMJ-VPUMZWJWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010155 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.78	ALOGPS
logP	4.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.37 m³·mol⁻¹	ChemAxon
Polarizability	45.52 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	splash10-02wa-0309000000-107696c445ee2097f3ad	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-2200690000-116b9b25c9a86c4f4259	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 (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_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
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-0973000000-c05ff42fd008465bafb3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0009000000-5dee4fb39c808ac6bd6b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0009000000-a3abedb65cc015b126a4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-0973000000-27eab1754ab850b5d833	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-8cbf377d4ac0ead7f478	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i0-0009000000-f445f21e6bb19a3e03e2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0400-3519000000-e95ed419ca30aa610aad	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-d2798e61ab8bdbb8b70c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-1009000000-08abf1a9cb419252bf5a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9006000000-1e75d302e82f8e8c004f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0596-0009000000-e1273a9cf6cd8fec5090	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-2295000000-496364ed24778803b66a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9620000000-568df3571bdbbb289061	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-0312986dad14766b7b5a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0009000000-9c3b566629f1b019e8c8	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1079000000-22dd9a5f612d7b635280	2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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
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

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0000328

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021953

KNApSAcK ID

Not Available

Chemspider ID

2338365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5317

PubChem Compound

3080612

PDB ID

Not Available

ChEBI ID

803536

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Reddy B, Engle A, Katsifis S, Simi B, Bartram HP, Perrino P, Mahan C: Biochemical epidemiology of colon cancer: effect of types of dietary fiber on fecal mutagens, acid, and neutral sterols in healthy subjects. Cancer Res. 1989 Aug 15;49(16):4629-35. [PubMed:2545348 ]
Andersen E, Karlaganis G, Sjovall J: Altered bile acid profiles in duodenal bile and urine in diabetic subjects. Eur J Clin Invest. 1988 Apr;18(2):166-72. doi: 10.1111/j.1365-2362.1988.tb02408.x. [PubMed:3133222 ]
Barker GM, Radley S, Bain I, Davis A, Lawson AM, Keighley MR, Neoptolemos JP: Biliary bile acid profiles in patients with familial adenomatous polyposis before and after colectomy. Br J Surg. 1994 Mar;81(3):441-4. doi: 10.1002/bjs.1800810340. [PubMed:8173925 ]
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Showing metabocard for 12-Ketodeoxycholic acid (MMDBc0031985)

MOL for #<Metabolite:0x00007fdb5a1a8b40>

3D MOL for #<Metabolite:0x00007fdb5a1a8b40>

3D SDF for #<Metabolite:0x00007fdb5a1a8b40>

3D-SDF for #<Metabolite:0x00007fdb5a1a8b40>

PDB for #<Metabolite:0x00007fdb5a1a8b40>

3D PDB for #<Metabolite:0x00007fdb5a1a8b40>

SMILES for #<Metabolite:0x00007fdb5a1a8b40>

INCHI for #<Metabolite:0x00007fdb5a1a8b40>

Structure for #<Metabolite:0x00007fdb5a1a8b40>

3D Structure for #<Metabolite:0x00007fdb5a1a8b40>