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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (8) Show 9 proteins XML

enzymes (1)transporters (8) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:01 UTC

HMDB ID

HMDB0000385

Secondary Accession Numbers

HMDB00385

Metabolite Identification

Common Name

12a-Hydroxy-3-oxocholadienic acid

Description

12a-Hydroxy-3-oxocholadienic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

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


  Mrv0541 02231218292D          

 28 31  0  0  1  0            999 V2000
    8.8602   -4.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636   -6.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3986   -5.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2088   -5.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8502   -8.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5739   -8.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5949   -6.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0949   -7.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4815   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7355   -7.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592   -7.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4216   -8.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9066   -6.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3981   -5.3067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1453   -8.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -8.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5927   -7.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1254   -6.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3163   -7.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8878   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303   -5.8937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2921   -4.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1641   -7.5107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3351   -6.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9931   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5496   -5.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5649   -3.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8301   -4.8474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  6  0  0  0
 23  2  1  1  0  0  0
 24  3  1  1  0  0  0
  4 14  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5 15  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
  7  8  1  0  0  0  0
 19  8  1  0  0  0  0
  9 22  1  0  0  0  0
 10 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 23  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 20 13  1  0  0  0  0
 13 21  1  0  0  0  0
 14 18  1  0  0  0  0
 15 23  1  0  0  0  0
 16 25  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 24  1  0  0  0  0
 19 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 26  1  6  0  0  0
 21 24  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
M  END

HMDB0000385
     RDKit          3D
12a-Hydroxy-3-oxocholadienic acid
 62 65  0  0  0  0  0  0  0  0999 V2000
   -4.1835    1.3168   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2072    0.2188   -0.3185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8848   -0.8680    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9681   -1.5572   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316   -0.7766   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4638   -0.8097   -1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8373   -0.0285    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    0.8336    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    1.8191   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899    1.9559   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0859    1.1241    1.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.5872    1.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.7626    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508    1.8670    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.8382    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945    0.9788   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739   -0.0549   -0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9865   -0.1600   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340   -0.9862   -1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843   -0.6886   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.4328    0.2583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2256   -1.5188    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9511   -0.5345    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -1.0633   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.1243    0.1973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1168   -1.4637   -0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.0267    0.9338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2868   -0.4185    2.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412    1.6500    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    1.1496   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5926    2.2512   -0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -0.1872   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011   -0.4048    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2032   -1.6840    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -2.4144    0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -2.1516   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7028    0.3993   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.4607    1.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929    1.5516   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    2.8455   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    3.0480    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.7408   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3270    1.7507    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975    0.2316    2.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102    2.5707    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758    2.7728    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7096    1.9360    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0965   -2.0392   -1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8719   -0.7197   -2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0312    0.2438   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385   -1.5890   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -1.8348    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -2.4246    0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -1.1449    1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -1.4245    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -2.1392   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -0.5807   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325   -2.0706    0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -1.9553   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    0.1797    3.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694   -0.3976    2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454   -1.4630    2.4914 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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  1
 26 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END


  Mrv0541 02231218292D          

 28 31  0  0  1  0            999 V2000
    8.8602   -4.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636   -6.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3986   -5.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2088   -5.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8502   -8.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5739   -8.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5949   -6.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0949   -7.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4815   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7355   -7.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592   -7.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4216   -8.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9066   -6.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3981   -5.3067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1453   -8.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -8.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5927   -7.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1254   -6.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3163   -7.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8878   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303   -5.8937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2921   -4.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1641   -7.5107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3351   -6.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9931   -8.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5496   -5.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5649   -3.4433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8301   -4.8474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  6  0  0  0
 23  2  1  1  0  0  0
 24  3  1  1  0  0  0
  4 14  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5 15  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
  7  8  1  0  0  0  0
 19  8  1  0  0  0  0
  9 22  1  0  0  0  0
 10 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 23  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 20 13  1  0  0  0  0
 13 21  1  0  0  0  0
 14 18  1  0  0  0  0
 15 23  1  0  0  0  0
 16 25  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 24  1  0  0  0  0
 19 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 26  1  6  0  0  0
 21 24  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000385

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O4/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/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1

> <INCHI_KEY>
DJVAMCYXFUWMLS-RVOJYKBWSA-N

> <FORMULA>
C24H34O4

> <MOLECULAR_WEIGHT>
386.5244

> <EXACT_MASS>
386.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.63938568500029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.5910040636666665

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.93748577624332

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6706144451678595

> <JCHEM_PKA_STRONGEST_BASIC>
-0.34612030596180665

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
110.11199999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12a-hydroxy-3-oxocholadienate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000385
     RDKit          3D
12a-Hydroxy-3-oxocholadienic acid
 62 65  0  0  0  0  0  0  0  0999 V2000
   -4.1835    1.3168   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2072    0.2188   -0.3185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8848   -0.8680    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9681   -1.5572   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316   -0.7766   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4638   -0.8097   -1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8373   -0.0285    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    0.8336    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    1.8191   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899    1.9559   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0859    1.1241    1.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.5872    1.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.7626    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508    1.8670    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.8382    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945    0.9788   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739   -0.0549   -0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9865   -0.1600   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340   -0.9862   -1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843   -0.6886   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.4328    0.2583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2256   -1.5188    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9511   -0.5345    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -1.0633   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.1243    0.1973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1168   -1.4637   -0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.0267    0.9338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2868   -0.4185    2.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412    1.6500    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    1.1496   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5926    2.2512   -0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -0.1872   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011   -0.4048    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2032   -1.6840    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -2.4144    0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -2.1516   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7028    0.3993   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.4607    1.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929    1.5516   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    2.8455   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    3.0480    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.7408   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3270    1.7507    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975    0.2316    2.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102    2.5707    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758    2.7728    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7096    1.9360    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0965   -2.0392   -1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8719   -0.7197   -2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0312    0.2438   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385   -1.5890   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -1.8348    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -2.4246    0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -1.1449    1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -1.4245    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -2.1392   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -0.5807   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325   -2.0706    0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -1.9553   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    0.1797    3.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694   -0.3976    2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454   -1.4630    2.4914 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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  1
 26 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  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  C   UNK     0      16.539  -8.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.319 -12.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.677 -10.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.056  -9.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.787 -16.360   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.138 -15.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.910 -12.626   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.977 -13.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.565  -8.167   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.840 -13.959   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.191 -13.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.120 -16.299   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.892 -11.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.543  -9.906   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.471 -15.560   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.805 -15.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.173 -14.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.034 -11.359   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.524 -13.341   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.857 -13.281   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.243 -11.002   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.079  -7.881   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.506 -14.020   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.559 -11.802   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.454 -16.238   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      14.093  -9.462   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      21.588  -6.427   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.083  -9.048   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   14    9                                                       
CONECT    5    6   15                                                       
CONECT    6    5   17                                                       
CONECT    7   18    8                                                       
CONECT    8    7   19                                                       
CONECT    9    4   22                                                       
CONECT   10   16   11                                                       
CONECT   11   10   23                                                       
CONECT   12   15   16                                                       
CONECT   13   20   21                                                       
CONECT   14    1    4   18                                                  
CONECT   15    5   12   23                                                  
CONECT   16   10   12   25                                                  
CONECT   17    6   19   20                                                  
CONECT   18    7   14   24                                                  
CONECT   19    8   17   24                                                  
CONECT   20   13   17   23                                                  
CONECT   21   13   26   24                                                  
CONECT   22    9   27   28                                                  
CONECT   23    2   11   15   20                                             
CONECT   24    3   18   19   21                                             
CONECT   25   16                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0000385
HETATM    1  C1  UNL     1      -4.184   1.317  -0.656  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.207   0.219  -0.319  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.885  -0.868   0.393  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.968  -1.557  -0.361  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.132  -0.777  -0.779  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.464  -0.810  -1.997  1.00  0.00           O  
HETATM    7  O2  UNL     1      -6.837  -0.028   0.157  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.042   0.834   0.348  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.355   1.819  -0.544  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.090   1.956  -0.065  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.086   1.124   1.157  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.412   0.587   1.613  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.262   1.763   1.836  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.451   1.867   1.312  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.028   0.838   0.471  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.194   0.979  -0.133  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.774  -0.055  -0.977  1.00  0.00           C  
HETATM   18  O3  UNL     1       6.987  -0.160  -1.143  1.00  0.00           O  
HETATM   19  C16 UNL     1       4.834  -0.986  -1.636  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.384  -0.689  -1.234  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.319  -0.433   0.258  1.00  0.00           C  
HETATM   22  C19 UNL     1       4.226  -1.519   0.868  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.951  -0.534   0.826  1.00  0.00           C  
HETATM   24  C21 UNL     1       1.000  -1.063  -0.226  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.428  -1.124   0.197  1.00  0.00           C  
HETATM   26  O4  UNL     1      -1.117  -1.464  -0.988  1.00  0.00           O  
HETATM   27  C23 UNL     1      -0.971   0.027   0.934  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.287  -0.419   2.376  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.741   1.650   0.253  1.00  0.00           H  
HETATM   30  H2  UNL     1      -4.802   1.150  -1.533  1.00  0.00           H  
HETATM   31  H3  UNL     1      -3.593   2.251  -0.931  1.00  0.00           H  
HETATM   32  H4  UNL     1      -2.948  -0.187  -1.357  1.00  0.00           H  
HETATM   33  H5  UNL     1      -4.401  -0.405   1.297  1.00  0.00           H  
HETATM   34  H6  UNL     1      -3.203  -1.684   0.750  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.409  -2.414   0.260  1.00  0.00           H  
HETATM   36  H8  UNL     1      -4.539  -2.152  -1.237  1.00  0.00           H  
HETATM   37  H9  UNL     1      -7.703   0.399  -0.151  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.468   1.461   1.200  1.00  0.00           H  
HETATM   39  H11 UNL     1      -1.393   1.552  -1.628  1.00  0.00           H  
HETATM   40  H12 UNL     1      -1.827   2.846  -0.449  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.267   3.048   0.186  1.00  0.00           H  
HETATM   42  H14 UNL     1       0.828   1.741  -0.832  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.327   1.751   1.987  1.00  0.00           H  
HETATM   44  H16 UNL     1       1.197   0.232   2.687  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.910   2.571   2.446  1.00  0.00           H  
HETATM   46  H18 UNL     1       4.076   2.773   1.498  1.00  0.00           H  
HETATM   47  H19 UNL     1       5.710   1.936   0.042  1.00  0.00           H  
HETATM   48  H20 UNL     1       5.097  -2.039  -1.548  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.872  -0.720  -2.734  1.00  0.00           H  
HETATM   50  H22 UNL     1       3.031   0.244  -1.730  1.00  0.00           H  
HETATM   51  H23 UNL     1       2.839  -1.589  -1.563  1.00  0.00           H  
HETATM   52  H24 UNL     1       3.745  -1.835   1.843  1.00  0.00           H  
HETATM   53  H25 UNL     1       4.265  -2.425   0.266  1.00  0.00           H  
HETATM   54  H26 UNL     1       5.209  -1.145   1.148  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.992  -1.424   1.549  1.00  0.00           H  
HETATM   56  H28 UNL     1       1.312  -2.139  -0.416  1.00  0.00           H  
HETATM   57  H29 UNL     1       1.069  -0.581  -1.205  1.00  0.00           H  
HETATM   58  H30 UNL     1      -0.532  -2.071   0.819  1.00  0.00           H  
HETATM   59  H31 UNL     1      -0.568  -1.955  -1.619  1.00  0.00           H  
HETATM   60  H32 UNL     1      -0.771   0.180   3.133  1.00  0.00           H  
HETATM   61  H33 UNL     1      -2.369  -0.398   2.570  1.00  0.00           H  
HETATM   62  H34 UNL     1      -0.945  -1.463   2.491  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   14   45
CONECT   14   15   46
CONECT   15   16   16   21
CONECT   16   17   47
CONECT   17   18   18   19
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   23
CONECT   22   52   53   54
CONECT   23   24   55
CONECT   24   25   56   57
CONECT   25   26   27   58
CONECT   26   59
CONECT   27   28
CONECT   28   60   61   62
END

HMDB0000385
     RDKit          3D
12a-Hydroxy-3-oxocholadienic acid
 62 65  0  0  0  0  0  0  0  0999 V2000
   -4.1835    1.3168   -0.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2072    0.2188   -0.3185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8848   -0.8680    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9681   -1.5572   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316   -0.7766   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4638   -0.8097   -1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8373   -0.0285    0.1566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0425    0.8336    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    1.8191   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899    1.9559   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0859    1.1241    1.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122    0.5872    1.6127 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    1.7626    1.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4508    1.8670    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.8382    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945    0.9788   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7739   -0.0549   -0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9865   -0.1600   -1.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340   -0.9862   -1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843   -0.6886   -1.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.4328    0.2583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2256   -1.5188    0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9511   -0.5345    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -1.0633   -0.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.1243    0.1973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1168   -1.4637   -0.9881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.0267    0.9338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2868   -0.4185    2.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412    1.6500    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    1.1496   -1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5926    2.2512   -0.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -0.1872   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4011   -0.4048    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2032   -1.6840    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -2.4144    0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386   -2.1516   -1.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7028    0.3993   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677    1.4607    1.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929    1.5516   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267    2.8455   -0.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    3.0480    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8278    1.7408   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3270    1.7507    1.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1975    0.2316    2.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102    2.5707    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0758    2.7728    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7096    1.9360    0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0965   -2.0392   -1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8719   -0.7197   -2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0312    0.2438   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8385   -1.5890   -1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -1.8348    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2645   -2.4246    0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -1.1449    1.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921   -1.4245    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117   -2.1392   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -0.5807   -1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325   -2.0706    0.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5679   -1.9553   -1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713    0.1797    3.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694   -0.3976    2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454   -1.4630    2.4914 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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  1
 27  8  1  0
 27 11  1  0
 23 12  1  0
 21 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  7 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  1
 26 59  1  0
 28 60  1  0
 28 61  1  0
 28 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12a-Hydroxy-3-oxocholadienate	Generator
12a-Hydroxy-3-oxo-4,6-choladien-24-Oate	HMDB
12a-Hydroxy-3-oxo-4,6-choladien-24-Oic acid	HMDB
12a-Hydroxy-3-oxo-chola-4,6-dienate	HMDB
12a-Hydroxy-3-oxo-chola-4,6-dienic acid	HMDB
12a-Hydroxy-3-oxochola-4,6-dienate	HMDB
12a-Hydroxy-3-oxochola-4,6-dienic acid	HMDB
(4R)-4-[(2R,15R,16S)-16-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoate	HMDB
12alpha-Hydroxy-3-oxocholadienate	HMDB
12Α-hydroxy-3-oxocholadienate	HMDB
12Α-hydroxy-3-oxocholadienic acid	HMDB
12a-Hydroxy-3-oxocholadienic acid	Generator

Chemical Formula

C₂₄H₃₄O₄

Average Molecular Weight

386.5244

Monoisotopic Molecular Weight

386.245709576

IUPAC Name

(4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid

Traditional Name

12a-hydroxy-3-oxocholadienate

CAS Registry Number

13535-96-1

SMILES

C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C

InChI Identifier

InChI=1S/C24H34O4/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/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1

InChI Key

DJVAMCYXFUWMLS-RVOJYKBWSA-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-oxosteroid
12-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
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

Not Available

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Depression (PMID: 35445772)

Alzheimer's Disease (PMID: 30337151)

Cancer

Colorectal cancer (PMID: 21724466)

Digestive system disorder

Gastrointestinal disorder

Chronic diarrhea (PMID: 19900947)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0000385)
Cell membrane (HMDB: HMDB0000385)

Biofluid or Excreta

Urine (HMDB: HMDB0000385)

Tissue substructure

Hepatic tissue (HMDB: HMDB0000385)

Organ

Cellular substructure

Extracellular (HMDB: HMDB0000385)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31643938)
Bile (PMID: 31643938)

Excreta

Biofluid or Excreta

Feces (PMID: 31643938)
Urine (PMID: 1112456)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000385)

Source

Endogenous

Endogenous (HMDB: HMDB0000385)

Animal

Animal (HMDB: HMDB0000385)

Exogenous

Food

Food (HMDB: HMDB0000385)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0000385)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0000385)

Cellular process

Cell signaling (HMDB: HMDB0000385)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0000385)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.49	ALOGPS
logP	3.59	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-0.35	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	110.11 m³·mol⁻¹	ChemAxon
Polarizability	43.64 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.618	31661259
DarkChem	[M-H]-	183.023	31661259
AllCCS	[M+H]+	198.267	32859911
AllCCS	[M-H]-	199.646	32859911
DeepCCS	[M-2H]-	221.862	30932474
DeepCCS	[M+Na]+	197.089	30932474
AllCCS	[M+H]+	198.3	32859911
AllCCS	[M+H-H2O]+	195.8	32859911
AllCCS	[M+NH4]+	200.5	32859911
AllCCS	[M+Na]+	201.1	32859911
AllCCS	[M-H]-	199.6	32859911
AllCCS	[M+Na-2H]-	200.6	32859911
AllCCS	[M+HCOO]-	201.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12a-Hydroxy-3-oxocholadienic acid	C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C	4481.5	Standard polar	33892256
12a-Hydroxy-3-oxocholadienic acid	C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C	3111.1	Standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid	C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C	3653.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12a-Hydroxy-3-oxocholadienic acid,1TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@@]21C	3479.9	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,1TMS,isomer #2	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3493.3	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,1TMS,isomer #3	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O)[C@@]21C	3533.3	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3444.3	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O)[C@@]21C	3469.6	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TMS,isomer #3	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3487.1	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3393.8	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3361.4	Standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C)[C@@]21C	3747.2	Standard polar	33892256
12a-Hydroxy-3-oxocholadienic acid,1TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@@]21C	3743.8	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,1TBDMS,isomer #2	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3739.7	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,1TBDMS,isomer #3	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O)[C@@]21C	3774.3	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3962.1	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TBDMS,isomer #2	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O)[C@@]21C	3936.1	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,2TBDMS,isomer #3	C[C@H](CCC(=O)O)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	3937.8	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	4045.0	Semi standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	4009.0	Standard non polar	33892256
12a-Hydroxy-3-oxocholadienic acid,3TBDMS,isomer #1	C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C=CC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)C3C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C	4014.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08mi-1749000000-de114046c628c58a5edd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (2 TMS) - 70eV, Positive	splash10-014i-2191170000-9998846ffacee5e0677f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 10V, Positive-QTOF	splash10-0gb9-0009000000-290d4eb4d249b16fe3e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 20V, Positive-QTOF	splash10-0lkc-0009000000-d7e470c0215474a29520	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 40V, Positive-QTOF	splash10-0aor-5219000000-a8d56d9c39447200b4ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 10V, Negative-QTOF	splash10-000i-0009000000-b0caf18090f9ef4bb293	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 20V, Negative-QTOF	splash10-014r-0009000000-669414e6c6b47067fe22	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 40V, Negative-QTOF	splash10-0a4l-9006000000-dd833c9fd22521dce774	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 10V, Negative-QTOF	splash10-000i-0009000000-c8a026dd6116a869f596	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 20V, Negative-QTOF	splash10-000i-0009000000-4e9f4a976c84950f587b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 40V, Negative-QTOF	splash10-00li-0098000000-686efde5f229f343a4f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 10V, Positive-QTOF	splash10-00kr-0019000000-30bbb01212141ac76f2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 20V, Positive-QTOF	splash10-0fri-2179000000-03bf59bf72ad64ad8f03	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12a-Hydroxy-3-oxocholadienic acid 40V, Positive-QTOF	splash10-0adl-4931000000-9780a1a303ef6253957c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022003

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5374

PubChem Compound

53477691

PDB ID

Not Available

ChEBI ID

172621

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hayakawa, Shohei; Saburi, Yasuo; Fujii, Takao; Sonoda, Yoshiya. Microbiological degradation of bile acids. VII. Partial synthesis of 3,12-dioxo-D4,6-choladienic acid and its derivatives from cholic acid. Journal of Biochemistry (Tokyo, Japan) (1956), 43 731-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

Enzyme Details

1. Gastrotropin

General function:: Involved in binding
Specific function:: Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:: FABP6
Uniprot ID:: P51161
Molecular weight:: 14371.2

References

Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

Enzyme Details

2. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

Enzyme Details

5. Ileal sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:: SLC10A2
Uniprot ID:: Q12908
Molecular weight:: 37697.4

References

Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]

Enzyme Details

6. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

Enzyme Details

7. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

Enzyme Details

8. Solute carrier organic anion transporter family member 4A1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:: SLCO4A1
Uniprot ID:: Q96BD0
Molecular weight:: 77192.5

Showing metabocard for 12a-Hydroxy-3-oxocholadienic acid (HMDB0000385)

MOL for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

3D MOL for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

3D SDF for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

3D-SDF for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

PDB for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

3D PDB for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

SMILES for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

INCHI for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

Structure for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

3D Structure for HMDB0000385 (12a-Hydroxy-3-oxocholadienic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References