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Showing metabocard for 7b-Hydroxy-3-oxo-5b-cholanoic acid (HMDB0000541)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000541
Secondary Accession Numbers
  • HMDB00541
Metabolite Identification
Common Name7b-Hydroxy-3-oxo-5b-cholanoic acid
Description7b-Hydroxy-3-oxo-5b-cholanoic acid was one of the bile acids present in significant proportions during early gestation, identified in amniotic fluid. (PMID 2373959 ). 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
Data?1582752138
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

Untitled Document-6
  Mrv0541 02231218352D          

 32 35  0  0  0  0            999 V2000
   -3.3884   -1.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -1.5888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6739   -1.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2450   -2.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
M  STY  1   1 SUP
M  SAL   1  2  31  32
M  SBL   1  1  34
M  SMT   1 OCH3
M  END
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3D MOL for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

HMDB0000541
     RDKit          3D
7b-Hydroxy-3-oxo-5b-cholanoic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    7.5283    2.1403   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0550    0.1782    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6273   -0.1824   -0.8033 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  3  5  1  0
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 29 65  1  0
 29 66  1  0
 29 67  1  0
M  END
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3D SDF for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

Untitled Document-6
  Mrv0541 02231218352D          

 32 35  0  0  0  0            999 V2000
   -3.3884   -1.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3884   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739   -2.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -1.5888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6739   -1.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2450   -1.1763    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.2450   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9686   -0.0964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.3060    2.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 14 10  1  0  0  0  0
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 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 12 19  1  1  0  0  0
  5 20  1  1  0  0  0
  9 21  1  1  0  0  0
 18 22  1  6  0  0  0
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 25 26  2  0  0  0  0
  8 27  2  0  0  0  0
  2 28  2  0  0  0  0
 10 29  1  6  0  0  0
 11 30  1  6  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  STY  1   1 SUP
M  SAL   1  2  31  32
M  SBL   1  1  34
M  SMT   1 OCH3
M  END
> <DATABASE_ID>
HMDB0000541

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1

> <INCHI_KEY>
UZRRNRRCPZZPNY-ZECRIGHZSA-N

> <FORMULA>
C25H38O4

> <MOLECULAR_WEIGHT>
402.5668

> <EXACT_MASS>
402.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.31285335806791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.452214635000001

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.515993948009562

> <JCHEM_PKA_STRONGEST_BASIC>
-6.753737659695693

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
112.08959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7b-hydroxy-3-oxo-5b-cholanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

HMDB0000541
     RDKit          3D
7b-Hydroxy-3-oxo-5b-cholanoic acid
 67 70  0  0  0  0  0  0  0  0999 V2000
    7.5283    2.1403   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481    1.4221    0.5730 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0550    0.1782    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5419   -0.2601   -0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -0.5011    0.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7836   -0.9193    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9401    0.1512   -0.2778 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6653    0.9699   -1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.1824   -0.8033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5806   -1.1547   -1.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1038   -1.6081   -2.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5220   -0.7578   -1.0246 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7978   -1.0695   -0.3885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8812   -1.5311   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -1.8399   -2.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455   -1.6163   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5641   -0.2237   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7904    0.6609   -1.3204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1470    2.0029   -0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1372    2.5540   -1.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519    2.6039    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9209    1.6343    1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5576    0.2600    0.8549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6763   -0.6425    2.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2011    0.2737    0.2566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1183    0.8217    1.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226    0.0272    1.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678   -0.7495    0.0721 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7926   -2.2252    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3829    1.5241   -0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0531    2.6328   -1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9053    2.9535    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8527    0.0299    1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5325   -1.4748    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0664   -1.6831   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978   -1.3980    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7843    0.9000    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881    1.5386   -1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1800    0.2926   -2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    1.7872   -0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784    0.7683   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2718   -1.9888   -1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766   -0.6435   -2.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3354   -1.3912   -3.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -2.7012   -1.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018    0.2994   -1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7640   -1.7684    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9865   -1.7797   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3228   -2.3791    0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5539   -0.2830    0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9313    0.6778   -2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6306    0.1939   -1.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626    3.0270   -0.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967    3.4607    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1891    2.1259    1.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8561    1.5428    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -1.5611    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7587   -0.9441    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -0.0938    2.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858    0.9489   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5277    0.9696    2.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8104    1.8654    0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666    0.6987    1.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027   -0.6704    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0934   -2.8561    0.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6345   -2.6781   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -2.3616    1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  1
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  6
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  6
 13 47  1  1
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  6
 26 61  1  0
 26 62  1  0
 27 63  1  0
 27 64  1  0
 29 65  1  0
 29 66  1  0
 29 67  1  0
M  END
Download

PDB for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-6                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.325  -2.966   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.325  -4.506   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.991  -5.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.658  -4.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.658  -2.966   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.991  -2.196   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.324  -5.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.990  -4.506   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.990  -2.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.324  -2.196   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.343  -2.196   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.343  -0.656   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.990   0.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.324  -0.656   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.808  -2.672   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.713  -1.426   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.808  -0.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.284   1.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.504   0.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.056  -1.478   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.099  -4.055   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       1.195   2.374   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.790   1.605   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.266   3.070   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.772   3.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.861   2.301   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.343  -5.276   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -7.659  -5.276   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      -3.094  -0.862   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.113  -3.529   0.000  0.00  0.00           H+0
HETATM   31  O   OCH3     1       6.171   4.877   0.000  0.00  0.00           O+0
HETATM   32  C   OCH3     1       6.570   6.365   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   20                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   11   21                                             
CONECT   10    9    5   14   29                                             
CONECT   11    9   12   15   30                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   22   23                                                  
CONECT   19   12                                                            
CONECT   20    5                                                            
CONECT   21    9                                                            
CONECT   22   18                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25                                                            
CONECT   27    8                                                            
CONECT   28    2                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   32   25                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END
Download

3D PDB for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

COMPND    HMDB0000541
HETATM    1  C1  UNL     1       7.528   2.140  -0.169  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.548   1.422   0.573  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.055   0.178   0.152  1.00  0.00           C  
HETATM    4  O2  UNL     1       6.542  -0.260  -0.930  1.00  0.00           O  
HETATM    5  C3  UNL     1       5.059  -0.501   0.949  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.784  -0.919   0.275  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.940   0.151  -0.278  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.665   0.970  -1.345  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.627  -0.182  -0.803  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.581  -1.155  -1.966  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.104  -1.608  -2.029  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.522  -0.758  -1.025  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.798  -1.069  -0.389  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.881  -1.531  -1.256  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.707  -1.840  -2.417  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.245  -1.616  -0.672  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.564  -0.224  -0.125  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.790   0.661  -1.320  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.147   2.003  -0.811  1.00  0.00           C  
HETATM   20  O4  UNL     1      -6.137   2.554  -1.226  1.00  0.00           O  
HETATM   21  C17 UNL     1      -4.252   2.604   0.199  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.921   1.634   1.307  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.558   0.260   0.855  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.676  -0.642   2.083  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.201   0.274   0.257  1.00  0.00           C  
HETATM   26  C22 UNL     1      -1.118   0.822   1.109  1.00  0.00           C  
HETATM   27  C23 UNL     1       0.123   0.027   1.226  1.00  0.00           C  
HETATM   28  C24 UNL     1       0.568  -0.750   0.072  1.00  0.00           C  
HETATM   29  C25 UNL     1       0.793  -2.225   0.426  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.383   1.524  -0.459  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.053   2.633  -1.061  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.905   2.954   0.484  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.853   0.030   1.908  1.00  0.00           H  
HETATM   34  H5  UNL     1       5.533  -1.475   1.295  1.00  0.00           H  
HETATM   35  H6  UNL     1       4.066  -1.683  -0.481  1.00  0.00           H  
HETATM   36  H7  UNL     1       3.198  -1.398   1.122  1.00  0.00           H  
HETATM   37  H8  UNL     1       2.784   0.900   0.559  1.00  0.00           H  
HETATM   38  H9  UNL     1       2.888   1.539  -1.959  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.180   0.293  -2.034  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.278   1.787  -0.919  1.00  0.00           H  
HETATM   41  H12 UNL     1       1.178   0.768  -1.227  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.272  -1.989  -1.900  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.777  -0.644  -2.933  1.00  0.00           H  
HETATM   44  H15 UNL     1      -0.335  -1.391  -3.033  1.00  0.00           H  
HETATM   45  H16 UNL     1       0.014  -2.701  -1.909  1.00  0.00           H  
HETATM   46  H17 UNL     1      -0.502   0.299  -1.428  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.764  -1.768   0.476  1.00  0.00           H  
HETATM   48  H19 UNL     1      -4.987  -1.780  -1.482  1.00  0.00           H  
HETATM   49  H20 UNL     1      -4.323  -2.379   0.122  1.00  0.00           H  
HETATM   50  H21 UNL     1      -5.554  -0.283   0.407  1.00  0.00           H  
HETATM   51  H22 UNL     1      -3.931   0.678  -2.017  1.00  0.00           H  
HETATM   52  H23 UNL     1      -5.631   0.194  -1.895  1.00  0.00           H  
HETATM   53  H24 UNL     1      -3.363   3.027  -0.283  1.00  0.00           H  
HETATM   54  H25 UNL     1      -4.797   3.461   0.670  1.00  0.00           H  
HETATM   55  H26 UNL     1      -3.189   2.126   1.954  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.856   1.543   1.925  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.103  -1.561   2.004  1.00  0.00           H  
HETATM   58  H29 UNL     1      -4.759  -0.944   2.179  1.00  0.00           H  
HETATM   59  H30 UNL     1      -3.401  -0.094   2.993  1.00  0.00           H  
HETATM   60  H31 UNL     1      -2.286   0.949  -0.646  1.00  0.00           H  
HETATM   61  H32 UNL     1      -1.528   0.970   2.135  1.00  0.00           H  
HETATM   62  H33 UNL     1      -0.810   1.865   0.786  1.00  0.00           H  
HETATM   63  H34 UNL     1       0.967   0.699   1.548  1.00  0.00           H  
HETATM   64  H35 UNL     1       0.003  -0.670   2.100  1.00  0.00           H  
HETATM   65  H36 UNL     1      -0.093  -2.856   0.120  1.00  0.00           H  
HETATM   66  H37 UNL     1       1.635  -2.678  -0.117  1.00  0.00           H  
HETATM   67  H38 UNL     1       0.847  -2.362   1.531  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8    9   37
CONECT    8   38   39   40
CONECT    9   10   28   41
CONECT   10   11   42   43
CONECT   11   12   44   45
CONECT   12   13   28   46
CONECT   13   14   25   47
CONECT   14   15   15   16
CONECT   16   17   48   49
CONECT   17   18   23   50
CONECT   18   19   51   52
CONECT   19   20   20   21
CONECT   21   22   53   54
CONECT   22   23   55   56
CONECT   23   24   25
CONECT   24   57   58   59
CONECT   25   26   60
CONECT   26   27   61   62
CONECT   27   28   63   64
CONECT   28   29
CONECT   29   65   66   67
END
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SMILES for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C
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INCHI for HMDB0000541 (7b-Hydroxy-3-oxo-5b-cholanoic acid)

InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
7b-Hydroxy-3-oxo-5b-cholanoateGenerator
(5b,7b)-7-Hydroxy-3-oxo-cholan-24-OateHMDB
(5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oic acidHMDB
7b-Hydroxy-3-oxo-5b-cholan-24-OateHMDB
7b-Hydroxy-3-oxo-5b-cholan-24-Oic acidHMDB
Methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acidHMDB
Methyl 3,7-dioxocholan-24-Oic acidHMDB
Chemical FormulaC25H38O4
Average Molecular Weight402.5668
Monoisotopic Molecular Weight402.277009704
IUPAC Namemethyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate
Traditional Name7b-hydroxy-3-oxo-5b-cholanoate
CAS Registry Number77060-26-5
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1
InChI KeyUZRRNRRCPZZPNY-ZECRIGHZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentBile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Bile acid, alcohol, or derivatives
  • 3-oxosteroid
  • 7-oxosteroid
  • Oxosteroid
  • Fatty acid methyl ester
  • Fatty acid ester
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point171 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP3.74ALOGPS
logP4.45ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.52ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.09 m³·mol⁻¹ChemAxon
Polarizability47.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+196.01331661259
DarkChem[M-H]-192.15431661259
AllCCS[M+H]+201.65732859911
AllCCS[M-H]-201.97932859911
DeepCCS[M-2H]-239.82330932474
DeepCCS[M+Na]+215.19430932474
AllCCS[M+H]+201.732859911
AllCCS[M+H-H2O]+199.532859911
AllCCS[M+NH4]+203.632859911
AllCCS[M+Na]+204.232859911
AllCCS[M-H]-202.032859911
AllCCS[M+Na-2H]-203.432859911
AllCCS[M+HCOO]-205.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.8.39 minutes32390414
Predicted by Siyang on May 30, 202220.7674 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.46 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3302.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid502.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid268.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid217.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid596.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid816.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid911.0 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)88.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1643.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid605.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1809.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid458.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid512.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate255.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA449.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water9.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7b-Hydroxy-3-oxo-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C3088.1Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C3107.0Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C3455.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3265.7Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3268.5Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3726.6Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3194.6Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3222.1Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3708.1Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3294.1Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3247.7Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3702.4Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3306.7Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3279.3Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3695.8Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3252.1Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3287.1Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3733.3Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3267.5Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3301.6Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C)CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3729.6Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3206.3Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3219.2Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3734.3Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3222.6Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3270.3Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C)=CC4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3736.5Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3483.3Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3527.8Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3837.1Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3430.8Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3389.8Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3819.6Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3551.6Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3450.2Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3816.6Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3552.0Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3496.6Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,1TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3811.1Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3662.8Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3635.3Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #1COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3915.3Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3692.9Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3694.2Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #2COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3913.5Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3626.9Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3500.9Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #3COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3909.6Standard polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3643.9Semi standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3562.1Standard non polar33892256
7b-Hydroxy-3-oxo-5b-cholanoic acid,2TBDMS,isomer #4COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(O[Si](C)(C)C(C)(C)C)=CC4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3915.0Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022104
KNApSAcK IDNot Available
Chemspider ID17215969
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5526
PubChem Compound22833531
PDB IDNot Available
ChEBI ID172644
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Forlani, Roberto; Maietti, Silvia; Pedrini, Paola. Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids. Journal of Organic Chemistry (2002), 67(16), 5802-5806.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Goto J, Saisho Y, Nambara T: Studies on steroids. CCLII. Separation and characterization of 3-oxobile acids in serum by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1991 Jul 5;567(2):343-9. [PubMed:1939467 ]
  2. Nakagawa M, Setchell KD: Bile acid metabolism in early life: studies of amniotic fluid. J Lipid Res. 1990 Jun;31(6):1089-98. [PubMed:2373959 ]
  3. Koopman BJ, Wolthers BG, van der Molen JC, Nagel GT, Kruizinga W: Abnormal urinary bile acids in a patient suffering from cerebrotendinous xanthomatosis during oral administration of ursodeoxycholic acid. Biochim Biophys Acta. 1987 Feb 14;917(2):238-46. [PubMed:3801500 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]