MiMeDB: Showing metabocard for all-trans-Retinoic acid (MMDBc0047935)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:16:39 UTC

Update Date

2024-04-30 20:32:57 UTC

Metabolite ID

MMDBc0047935

Metabolite Identification

Common Name

all-trans-Retinoic acid

Description

all-trans-Retinoic acid is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID:17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).

Structure

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

HMDB0001852
     RDKit          3D
all-trans-Retinoic acid
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.4071   -0.9003    2.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8786   -0.5603    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -0.2909    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -0.3499    0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.0890    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.1585    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -0.5390    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771    0.1155   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2056    0.0669    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242    0.3523   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.3230   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -0.0197    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.6216   -1.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253    0.6405   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3945    0.3627   -0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878    0.9837   -2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.0206   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6660   -0.9241   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.4485   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8365   -0.1025   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6379    0.3975    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5102    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2253   -1.1774    3.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.8039    2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8548   -0.0435    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -0.6160    1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.2040   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    0.1920    2.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098   -1.5130    2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -0.7137    2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.3857   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170   -0.1921    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    0.6226   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7662   -0.8943    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.8391    1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516   -0.2498    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688    0.8777   -2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6232    1.9901   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.3192   -2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395   -1.6636   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -1.5404   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.8614   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.4470   -2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0998   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428   -1.1947   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085    0.4104   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7189    0.2973   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3923    1.4254    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974   -0.1021    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7594   -1.5169    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

      
  Mrv1652304202019462D          

 22 22  0  0  0  0            999 V2000
 9997.875010000.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.589510000.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.304010000.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.019510000.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.735110000.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.450610000.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.164110000.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.879710000.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.593210000.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.308710000.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.593210001.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.164110001.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.304010001.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4429 9998.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9730 9999.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.447810001.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.446510000.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.732010000.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7320 9999.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4465 9998.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1610 9999.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.161010000.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 16  1  0  0  0  0
 21 15  1  0  0  0  0
 21 14  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047935

> <DATABASE_NAME>
MIME

> <SMILES>
C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

> <INCHI_KEY>
SHGAZHPCJJPHSC-YCNIQYBTSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.845994315681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.66

> <JCHEM_LOGP>
5.014367711

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.996647744997455

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
97.79079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tretinoin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001852
     RDKit          3D
all-trans-Retinoic acid
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.4071   -0.9003    2.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8786   -0.5603    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -0.2909    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -0.3499    0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.0890    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.1585    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -0.5390    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771    0.1155   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2056    0.0669    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242    0.3523   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.3230   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -0.0197    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.6216   -1.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253    0.6405   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3945    0.3627   -0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878    0.9837   -2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.0206   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6660   -0.9241   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.4485   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8365   -0.1025   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6379    0.3975    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5102    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2253   -1.1774    3.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.8039    2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8548   -0.0435    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -0.6160    1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.2040   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    0.1920    2.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098   -1.5130    2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -0.7137    2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.3857   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170   -0.1921    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    0.6226   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7662   -0.8943    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.8391    1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516   -0.2498    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688    0.8777   -2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6232    1.9901   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.3192   -2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395   -1.6636   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -1.5404   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.8614   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.4470   -2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0998   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428   -1.1947   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085    0.4104   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7189    0.2973   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3923    1.4254    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974   -0.1021    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7594   -1.5169    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0    8662.7008667.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0348666.996   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3678667.766   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.7038666.996   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.0398667.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.3748666.996   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.7068667.766   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.0428666.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.3748667.766   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8674.7108666.996   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.3748669.306   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8670.7068669.306   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3678669.306   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.8938664.009   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.8838665.725   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.0368669.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.0338667.767   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8658.7008666.997   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.7008665.456   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8660.0338664.687   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8661.3678665.456   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8661.3678666.997   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7                                                            
CONECT   13    3                                                            
CONECT   14   21                                                            
CONECT   15   21                                                            
CONECT   16   17                                                            
CONECT   17   18   22   16                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   15   14                                             
CONECT   22   17   21    1                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0001852
HETATM    1  C1  UNL     1      -3.407  -0.900   2.799  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.879  -0.560   1.435  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.992  -0.291   0.506  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.569  -0.350   0.924  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.606  -0.089   0.109  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.819  -0.159   0.556  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.063  -0.539   1.949  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.777   0.115  -0.301  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.206   0.067   0.073  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.124   0.352  -0.834  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.530   0.323  -0.533  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.062  -0.020   0.785  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.393   0.622  -1.495  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.825   0.640  -1.366  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.395   0.363  -0.281  1.00  0.00           O  
HETATM   16  O2  UNL     1       8.588   0.984  -2.503  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.361   0.021  -0.870  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.666  -0.924  -1.863  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.905   1.448  -1.163  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.836  -0.102  -1.110  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.638   0.398   0.029  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.355  -0.510   1.233  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.225  -1.177   3.486  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.766  -1.804   2.701  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.855  -0.043   3.217  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.293  -0.616   1.940  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.737   0.204  -0.914  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.519   0.192   2.594  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.510  -1.513   2.126  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.083  -0.714   2.256  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.517   0.386  -1.313  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.517  -0.192   1.058  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.767   0.623  -1.862  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.766  -0.894   0.746  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.674   0.839   1.167  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.352  -0.250   1.572  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.969   0.878  -2.482  1.00  0.00           H  
HETATM   38  H16 UNL     1       8.623   1.990  -2.688  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.194  -0.319  -2.653  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.040  -1.664  -1.368  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.446  -1.540  -2.415  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.330   1.861  -0.337  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.359   1.447  -2.121  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.802   2.100  -1.337  1.00  0.00           H  
HETATM   45  H23 UNL     1      -5.043  -1.195  -1.216  1.00  0.00           H  
HETATM   46  H24 UNL     1      -5.109   0.410  -2.060  1.00  0.00           H  
HETATM   47  H25 UNL     1      -6.719   0.297  -0.181  1.00  0.00           H  
HETATM   48  H26 UNL     1      -5.392   1.425   0.331  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.797  -0.102   2.162  1.00  0.00           H  
HETATM   50  H28 UNL     1      -5.759  -1.517   1.012  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
CONECT    3    4   17
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    8    8
CONECT    7   28   29   30
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   13   13
CONECT   12   34   35   36
CONECT   13   14   37
CONECT   14   15   15   16
CONECT   16   38
CONECT   17   18   19   20
CONECT   18   39   40   41
CONECT   19   42   43   44
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   49   50
END

HMDB0001852
     RDKit          3D
all-trans-Retinoic acid
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.4071   -0.9003    2.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8786   -0.5603    1.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9920   -0.2909    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693   -0.3499    0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6056   -0.0890    0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -0.1585    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -0.5390    1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771    0.1155   -0.3009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2056    0.0669    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1242    0.3523   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297    0.3230   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0620   -0.0197    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.6216   -1.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253    0.6405   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3945    0.3627   -0.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878    0.9837   -2.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3611    0.0206   -0.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6660   -0.9241   -1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.4485   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8365   -0.1025   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6379    0.3975    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5102    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2253   -1.1774    3.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -1.8039    2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8548   -0.0435    3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -0.6160    1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.2040   -0.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    0.1920    2.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098   -1.5130    2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -0.7137    2.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5169    0.3857   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170   -0.1921    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    0.6226   -1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7662   -0.8943    0.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745    0.8391    1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3516   -0.2498    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9688    0.8777   -2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6232    1.9901   -2.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1943   -0.3192   -2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395   -1.6636   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -1.5404   -2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    1.8614   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3592    1.4470   -2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8018    2.0998   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428   -1.1947   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085    0.4104   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7189    0.2973   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3923    1.4254    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7974   -0.1021    2.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7594   -1.5169    1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
M  END

Synonyms

Value	Source
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)	ChEBI
AGN 100335	ChEBI
all-(e)-Retinoic acid	ChEBI
all-trans-beta-Retinoic acid	ChEBI
all-trans-Tretinoin	ChEBI
all-trans-Vitamin a acid	ChEBI
all-trans-Vitamin a1 acid	ChEBI
beta-Retinoic acid	ChEBI
Eudyna	ChEBI
Renova	ChEBI
Retin-a	ChEBI
Retinoic acid	ChEBI
Retisol-a	ChEBI
Ro 1-5488	ChEBI
Solage	ChEBI
Stieva-a	ChEBI
trans-Retinoic acid	ChEBI
Tretin m	ChEBI
Tretinoin	ChEBI
Vesanoid	ChEBI
Vitamin a acid	ChEBI
Vitinoin	ChEBI
all-trans-Retinoate	Kegg
Avita	Kegg
Retin a	Kegg
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)	Generator
all-(e)-Retinoate	Generator
all-trans-b-Retinoate	Generator
all-trans-b-Retinoic acid	Generator
all-trans-beta-Retinoate	Generator
all-trans-Β-retinoate	Generator
all-trans-Β-retinoic acid	Generator
b-Retinoate	Generator
b-Retinoic acid	Generator
beta-Retinoate	Generator
Β-retinoate	Generator
Β-retinoic acid	Generator
Retinoate	Generator
trans-Retinoate	Generator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate	HMDB
Tretinoin zinc salt	HMDB
trans Retinoic acid	HMDB
Acid, all-trans-retinoic	HMDB
Salt, tretinoin sodium	HMDB
beta all trans Retinoic acid	HMDB
beta-all-trans-Retinoic acid	HMDB
Acid, vitamin a	HMDB
Potassium salt, tretinoin	HMDB
Sodium salt, tretinoin	HMDB
Acid, beta-all-trans-retinoic	HMDB
Tretinoin potassium salt	HMDB
Zinc salt, tretinoin	HMDB
Acid, retinoic	HMDB
Acid, trans-retinoic	HMDB
Salt, tretinoin potassium	HMDB
Salt, tretinoin zinc	HMDB
Tretinoin sodium salt	HMDB
all trans Retinoic acid	HMDB
Retin-a micro	HMDB
Atralin	HMDB
Tretin-X	HMDB
all-trans-Retinoic acid	MeSH

Molecular Formula

C₂₀H₂₈O₂

Average Mass

300.442

Monoisotopic Mass

300.208930142

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Traditional Name

tretinoin

CAS Registry Number

302-79-4

SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChI Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoic acid (CHEBI:15367 )
Retinoids (C00777 )
Retinoids (LMPR01090019 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0048 g/L	ALOGPS
logP	5.66	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	splash10-000i-2090000000-db078f48efb8038384f2	2018-04-09	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0009000000-12dbd83959268dee6dbf	2018-05-28	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-066r-4900000000-31c9262cbbf0bad5b738	2018-05-28	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fsl-9600000000-c6681587f0a9ae7a712e	2018-05-28	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0mc0-4941000000-401db468e6db7c5bbb5a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0090000000-d05c305f987a713dfaa0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0239000000-09da873ecbe1e09a1602	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-dca272cadb8a3ba3f819	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-016r-9630000000-553ddaf9452713df67ee	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0390000000-241af7f979164ecfbf34	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0mc0-4941000000-05bed4117d9ed953a2ca	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9400000000-3ecfeb7f6c8384d2a0d3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0239000000-2c6852256fcbebe1a2aa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0910000000-a1c1aa8b35e78558cd5b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uei-0494000000-28e6366fdd47e8ba2117	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-2980000000-3e7fc78de83c23830416	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-5900000000-ef4d86f8bcf86959f794	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-0090000000-e07ffb4c1e5c63ab1b59	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-0090000000-a0a8411213bbd2543243	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-3690000000-97e6a74798dd69c30ad1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zir-0973000000-3040e9e4a1a5448efbcb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-060c-1950000000-f3b9c9b378f60b8c49a9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ar3-5910000000-de22eb65f274483f3f98	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-0090000000-5f942e3b870e7bd0121b	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0190000000-22b445382d3977280045	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-4900000000-0005b37f6d54a42a84f6	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		2018-05-28	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		2018-05-28	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane
Nucleus

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Blood
Brain
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Liver
Lung
Neuron
Pancreas
Placenta
Platelet
Prostate
Spleen
Testis
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Brain
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Lung
Neuron
Pancreas
Placenta
Platelet
Prostate
Spleen
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191870	Retinal dehydrogenase 1	Unknown	P00352	Homo sapiens
MMDBp0191876	Retinal dehydrogenase 2	Unknown	O94788	Homo sapiens
MMDBp0192068	Cytochrome P450 4A11	Unknown	Q02928	Homo sapiens
MMDBp0192111	UDP-glucuronosyltransferase 2B28	Enzyme	Q9BY64	Homo sapiens
MMDBp0192118	UDP-glucuronosyltransferase 2B4	Enzyme	P06133	Homo sapiens
MMDBp0192135	UDP-glucuronosyltransferase 1-4	Enzyme	P22310	Homo sapiens
MMDBp0192136	UDP-glucuronosyltransferase 2B10	Enzyme	P36537	Homo sapiens
MMDBp0192137	UDP-glucuronosyltransferase 2B7	Enzyme	P16662	Homo sapiens
MMDBp0192138	UDP-glucuronosyltransferase 2B15	Enzyme	P54855	Homo sapiens
MMDBp0192139	UDP-glucuronosyltransferase 2A1	Enzyme	Q9Y4X1	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192141	UDP-glucuronosyltransferase 1-9	Enzyme	O60656	Homo sapiens
MMDBp0192142	UDP-glucuronosyltransferase 1-8	Enzyme	Q9HAW9	Homo sapiens
MMDBp0192143	UDP-glucuronosyltransferase 1-3	Enzyme	P35503	Homo sapiens
MMDBp0192144	UDP-glucuronosyltransferase 1-10	Enzyme	Q9HAW8	Homo sapiens
MMDBp0192145	UDP-glucuronosyltransferase 2B17	Enzyme	O75795	Homo sapiens
MMDBp0192146	UDP-glucuronosyltransferase 1-6	Enzyme	P19224	Homo sapiens
MMDBp0192147	UDP-glucuronosyltransferase 1-5	Enzyme	P35504	Homo sapiens
MMDBp0192148	UDP-glucuronosyltransferase 2B11	Enzyme	O75310	Homo sapiens
MMDBp0192151	UDP-glucuronosyltransferase 1-7	Enzyme	Q9HAW7	Homo sapiens
MMDBp0192630	Cytochrome P450 3A4	Unknown	P08684	Homo sapiens
MMDBp0192647	Cytochrome P450 2C9	Unknown	P11712	Homo sapiens
MMDBp0192649	Cytochrome P450 2C19	Unknown	P33261	Homo sapiens
MMDBp0193099	Cytochrome P450 2E1	Unknown	P05181	Homo sapiens
MMDBp0193101	Cytochrome P450 3A43	Unknown	Q9HB55	Homo sapiens
MMDBp0193102	Cytochrome P450 1B1	Unknown	Q16678	Homo sapiens
MMDBp0193104	Cytochrome P450 2C18	Unknown	P33260	Homo sapiens
MMDBp0193106	Cytochrome P450 2F1	Unknown	P24903	Homo sapiens
MMDBp0193107	Cytochrome P450 4X1	Unknown	Q8N118	Homo sapiens
MMDBp0193108	Cytochrome P450 2B6	Unknown	P20813	Homo sapiens
MMDBp0193109	Cytochrome P450 3A5	Unknown	P20815	Homo sapiens
MMDBp0193111	Cytochrome P450 2A13	Unknown	Q16696	Homo sapiens
MMDBp0193112	Cytochrome P450 3A7	Unknown	P24462	Homo sapiens
MMDBp0193113	Cytochrome P450 4B1	Unknown	P13584	Homo sapiens
MMDBp0193114	Cytochrome P450 4Z1	Unknown	Q86W10	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193116	Cytochrome P450 19A1	Unknown	P11511	Homo sapiens
MMDBp0193117	Cytochrome P450 2C8	Unknown	P10632	Homo sapiens
MMDBp0193118	Cytochrome P450 2S1	Unknown	Q96SQ9	Homo sapiens
MMDBp0193120	Cytochrome P450 2J2	Unknown	P51589	Homo sapiens
MMDBp0193121	Cytochrome P450 2A7	Unknown	P20853	Homo sapiens
MMDBp0193122	Cytochrome P450 2A6	Unknown	P11509	Homo sapiens
MMDBp0193321	Retinoic acid receptor gamma	Enzyme	P13631	Homo sapiens
MMDBp0193322	Retinoic acid receptor responder protein 1	Enzyme	P49788	Homo sapiens
MMDBp0193323	Retinoic acid receptor alpha	Enzyme	P10276	Homo sapiens
MMDBp0193326	Retinoic acid receptor beta	Enzyme	P10826	Homo sapiens
MMDBp0193327	Retinoic acid receptor RXR-beta	Enzyme	P28702	Homo sapiens
MMDBp0193330	Retinoic acid receptor RXR-gamma	Enzyme	P48443	Homo sapiens
MMDBp0193331	Cellular retinoic acid-binding protein 1	Transporter	P29762	Homo sapiens
MMDBp0193333	Retinoic acid receptor RXR-alpha	Enzyme	P19793	Homo sapiens
MMDBp0193334	Cellular retinoic acid-binding protein 2	Transporter	P29373	Homo sapiens
MMDBp0194070	Cytochrome P450 4A22	Unknown	Q5TCH4	Homo sapiens
MMDBp0194142	UDP-glucuronosyltransferase 2A3	Enzyme	Q6UWM9	Homo sapiens
MMDBp0194192	Cytochrome P450, family 1, subfamily A, polypeptide 1	Enzyme	A0N0X8	Homo sapiens
MMDBp0195932	HCG2039726, isoform CRA_f	Enzyme	Q5DT02	Homo sapiens
MMDBp0195933	HCG2039726, isoform CRA_e	Enzyme	Q5DSZ6	Homo sapiens
MMDBp0195934	UDP glycosyltransferase 1 family polypeptide A7	Enzyme	Q5DSZ7	Homo sapiens
MMDBp0196019	Cytochrome P450 2D6	Enzyme	Q6NWU0	Homo sapiens
MMDBp0196394	Nuclear receptor corepressor 2	Unknown	Q9Y618	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001829	Oxygen	4-Oxo-13-Cis-Retinoate	Not Available	4-Oxo-Retinoic Acid Formation (Oxidation)	VMH	1503811
MMDBr0002049	Water	Hydrogen Ion	Not Available	Retinal Dehydrogenase	VMH; KEGG	30371894
MMDBr0002050	Water	Hydrogen Ion	Not Available	Retinal Dehydrogenase (NADPH)	VMH	1503811
MMDBr0002053	Hydrogen Ion	Water	Not Available	Retinoic Acid Hydroxylation (P450)	VMH	1503811
MMDBr0002056	all-trans-Retinoic acid	13-cis-Retinoic acid	Glutathione s-transferase mu 1	13-Cis-Retinoic Acid Isomerase	VMH	1503811 9677409 9806904
MMDBr0002058	all-trans-Retinoic acid	all-trans-Retinoic acid	Not Available	Retinoate Transport, Nuclear	VMH	1503811
MMDBr0002072	Adenosine triphosphate	Adenosine monophosphate	Not Available	Retinoyl Coenzyme A Formation	VMH	1503811
MMDBr0002077	all-trans-Retinoic acid	all-trans-Retinoic acid	Not Available	Retinoic Acid Transport	VMH	8630327
MMDBr0002078	all-trans-Retinoic acid	all-trans-Retinoic acid	Not Available	Retinoic Acid Transport in Er	VMH	14704335
MMDBr0002332	all-trans-Retinoic acid	Retinoyl b-glucuronide	Udp glucuronosyltransferase 1 family, polypeptide a1	UDP-Glucuronosyltransferase 1-10 Precursor, Microsomal	VMH	15117964 9295054
MMDBr0003501	Acetoacetic acid	Acetoacetic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003509	2-Hydroxybutyric acid	2-Hydroxybutyric acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003516	Pyruvic acid	Pyruvic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003524	Oxoglutaric acid	Oxoglutaric acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003531	Acetic acid	Acetic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003536	Formic acid	Formic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003540	Propionic acid	Propionic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003545	L-Lactic acid	L-Lactic acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003547	Butyric acid	Butyric acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0003549	(R)-3-Hydroxybutyric acid	(R)-3-Hydroxybutyric acid	Solute carrier family 16 (monocarboxylate transporter), member 1	Major Facilitator (Mfs) Tcdb:2.A.1.13.1	VMH	12739169
MMDBr0004135	Hydrogen Ion	all-trans-18-Hydroxyretinoic acid	Not Available	RE1943C	VMH	10823918 12091498
MMDBr0004136	Hydrogen Ion	all-trans-18-Hydroxyretinoic acid	Cytochrome p450 family 26 subfamily b member 1	RE1943R	VMH	10823918 12091498
MMDBr0004337	all-trans-Retinoic acid	13-cis-Retinoic acid	Not Available	RE2659R	VMH	9647871
MMDBr0004480	Water	Hydrogen Ion	Not Available	Retinal Dehydrogenase	VMH	10559215
MMDBr0010394	Water	Hydrogen Ion	Aldehyde dehydrogenase 1 family, member a1	Retinal:NAD+ Oxidoreductase	VMH; KEGG	30371894

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	22	Human feces; Human sputum; Human	Metabolic reconstruction
Bacteria	Firmicutes	4	Human feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0145	0.0092	uM	Adult (>18 years old)	Both	Normal	HMDB	2756924
Human Blood	Detected and Quantified	0.20	0.18	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 Adipose tissue	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Bladder	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	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 Kidney	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Lung	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Pancreas	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
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

HMDB0001852

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022710

KNApSAcK ID

Not Available

Chemspider ID

392618

KEGG Compound ID

C00777

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tretinoin

METLIN ID

Not Available

PubChem Compound

444795

PDB ID

Not Available

ChEBI ID

15367

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. doi: 10.1016/0753-3322(91)90101-x. [PubMed:1932598 ]
Barua AB, Olson JA: Retinoyl beta-glucuronide: an endogenous compound of human blood. Am J Clin Nutr. 1986 Apr;43(4):481-5. doi: 10.1093/ajcn/43.4.481. [PubMed:3962900 ]
Stewart ME, Benoit AM, Downing DT, Strauss JS: Suppression of sebum secretion with 13-cis-retinoic acid: effect on individual skin surface lipids and implications for their anatomic origin. J Invest Dermatol. 1984 Jan;82(1):74-8. doi: 10.1111/1523-1747.ep12259161. [PubMed:6228612 ]
Meyer E, Lambert WE, De Leenheer AP: Simultaneous determination of endogenous retinoic acid isomers and retinol in human plasma by isocratic normal-phase HPLC with ultraviolet detection. Clin Chem. 1994 Jan;40(1):48-57. [PubMed:8287543 ]
Lopez-Boado YS, Klaus M, Dawson MI, Lopez-Otin C: Retinoic acid-induced expression of apolipoprotein D and concomitant growth arrest in human breast cancer cells are mediated through a retinoic acid receptor RARalpha-dependent signaling pathway. J Biol Chem. 1996 Dec 13;271(50):32105-11. doi: 10.1074/jbc.271.50.32105. [PubMed:8943263 ]
Masgrau-Peya E, Salomon D, Saurat JH, Meda P: In vivo modulation of connexins 43 and 26 of human epidermis by topical retinoic acid treatment. J Histochem Cytochem. 1997 Sep;45(9):1207-15. doi: 10.1177/002215549704500904. [PubMed:9283608 ]
Thiboutot D, Martin P, Volikos L, Gilliland K: Oxidative activity of the type 2 isozyme of 17beta-hydroxysteroid dehydrogenase (17beta-HSD) predominates in human sebaceous glands. J Invest Dermatol. 1998 Sep;111(3):390-5. doi: 10.1046/j.1523-1747.1998.00322.x. [PubMed:9740229 ]
Giannini G, Di Marcotullio L, Ristori E, Zani M, Crescenzi M, Scarpa S, Piaggio G, Vacca A, Peverali FA, Diana F, Screpanti I, Frati L, Gulino A: HMGI(Y) and HMGI-C genes are expressed in neuroblastoma cell lines and tumors and affect retinoic acid responsiveness. Cancer Res. 1999 May 15;59(10):2484-92. [PubMed:10344762 ]
Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
Natsume N, Kondo S, Matsuyama Y, Sumida K, Inou H, Kawakami N, Sandell LJ, Iwata H: Analysis of cartilage-derived retinoic acid-sensitive protein in cerebrospinal fluid From patients With spinal diseases. Spine (Phila Pa 1976). 2001 Jan 15;26(2):157-60. doi: 10.1097/00007632-200101150-00009. [PubMed:11154535 ]
Paez-Pereda M, Kovalovsky D, Hopfner U, Theodoropoulou M, Pagotto U, Uhl E, Losa M, Stalla J, Grubler Y, Missale C, Arzt E, Stalla GK: Retinoic acid prevents experimental Cushing syndrome. J Clin Invest. 2001 Oct;108(8):1123-31. doi: 10.1172/JCI11098. [PubMed:11602619 ]
Saito S, Kondo S, Mishima S, Ishiguro N, Hasegawa Y, Sandell LJ, Iwata H: Analysis of cartilage-derived retinoic-acid-sensitive protein (CD-RAP) in synovial fluid from patients with osteoarthritis and rheumatoid arthritis. J Bone Joint Surg Br. 2002 Sep;84(7):1066-9. doi: 10.1302/0301-620x.84b7.12177. [PubMed:12358374 ]
Lee YF, Bao BY, Chang C: Modulation of the retinoic acid-induced cell apoptosis and differentiation by the human TR4 orphan nuclear receptor. Biochem Biophys Res Commun. 2004 Oct 22;323(3):876-83. doi: 10.1016/j.bbrc.2004.08.176. [PubMed:15381082 ]
Patel JB, Huynh CK, Handratta VD, Gediya LK, Brodie AM, Goloubeva OG, Clement OO, Nanne IP, Soprano DR, Njar VC: Novel retinoic acid metabolism blocking agents endowed with multiple biological activities are efficient growth inhibitors of human breast and prostate cancer cells in vitro and a human breast tumor xenograft in nude mice. J Med Chem. 2004 Dec 30;47(27):6716-29. doi: 10.1021/jm0401457. [PubMed:15615521 ]
Tse HK, Leung MB, Woolf AS, Menke AL, Hastie ND, Gosling JA, Pang CP, Shum AS: Implication of Wt1 in the pathogenesis of nephrogenic failure in a mouse model of retinoic acid-induced caudal regression syndrome. Am J Pathol. 2005 May;166(5):1295-307. doi: 10.1016/S0002-9440(10)62349-8. [PubMed:15855632 ]
Baron JM, Heise R, Blaner WS, Neis M, Joussen S, Dreuw A, Marquardt Y, Saurat JH, Merk HF, Bickers DR, Jugert FK: Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J Invest Dermatol. 2005 Jul;125(1):143-53. doi: 10.1111/j.0022-202X.2005.23791.x. [PubMed:15982314 ]
Mercader J, Ribot J, Murano I, Felipe F, Cinti S, Bonet ML, Palou A: Remodeling of white adipose tissue after retinoic acid administration in mice. Endocrinology. 2006 Nov;147(11):5325-32. doi: 10.1210/en.2006-0760. Epub 2006 Jul 13. [PubMed:16840543 ]
Holland LZ: Developmental biology: a chordate with a difference. Nature. 2007 May 10;447(7141):153-5. doi: 10.1038/447153a. [PubMed:17495912 ]

Showing metabocard for all-trans-Retinoic acid (MMDBc0047935)

MOL for #<Metabolite:0x00007fa4a1fc68c0>

3D MOL for #<Metabolite:0x00007fa4a1fc68c0>

3D SDF for #<Metabolite:0x00007fa4a1fc68c0>

3D-SDF for #<Metabolite:0x00007fa4a1fc68c0>

PDB for #<Metabolite:0x00007fa4a1fc68c0>

3D PDB for #<Metabolite:0x00007fa4a1fc68c0>

SMILES for #<Metabolite:0x00007fa4a1fc68c0>

INCHI for #<Metabolite:0x00007fa4a1fc68c0>

Structure for #<Metabolite:0x00007fa4a1fc68c0>

3D Structure for #<Metabolite:0x00007fa4a1fc68c0>