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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (8) Show 10 proteins XML

enzymes (2)transporters (8) Show 10 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-14 18:32:47 UTC

Update Date

2022-03-07 02:49:34 UTC

HMDB ID

HMDB0006898

Secondary Accession Numbers

HMDB06898

Metabolite Identification

Common Name

Chenodeoxyglycocholic acid

Description

Chenodeoxyglycocholic acid is a glycine conjugated 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 02231220552D          

 32 35  0  0  1  0            999 V2000
   17.8568  -12.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8669  -13.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1547  -12.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4978  -11.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2798  -13.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7949  -14.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6908  -11.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4379  -14.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5813  -13.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1524  -14.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2958  -12.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1524  -15.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5813  -15.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0769  -12.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0498  -12.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8669  -15.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4379  -15.4377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7949  -13.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0102  -14.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5813  -14.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2958  -15.4377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1388  -11.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2699  -12.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2958  -14.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8669  -14.6127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0102  -13.3752    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3318  -11.4524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7234  -15.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0102  -15.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3937  -10.4963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7179  -11.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0149  -13.1933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
 25  2  1  1  0  0  0
 26  3  1  1  0  0  0
  4 15  1  0  0  0  0
  4  7  1  0  0  0  0
  5 18  1  0  0  0  0
  5  6  1  0  0  0  0
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  7 22  1  0  0  0  0
  8 10  1  0  0  0  0
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  9 20  1  0  0  0  0
  9 11  1  0  0  0  0
 10 25  1  0  0  0  0
 11 26  1  0  0  0  0
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 16 12  1  0  0  0  0
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 13 21  1  0  0  0  0
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 15 18  1  0  0  0  0
 16 25  1  0  0  0  0
 17 28  1  6  0  0  0
 18 26  1  0  0  0  0
 19 24  1  0  0  0  0
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 20 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 24  1  0  0  0  0
 21 29  1  6  0  0  0
 22 30  2  0  0  0  0
 22 27  1  0  0  0  0
 23 31  1  0  0  0  0
 23 32  2  0  0  0  0
M  END

HMDB0006898
     RDKit          3D
Chenodeoxyglycocholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.7180   -0.4015   -2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.6896   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720    0.9719   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -0.2341   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    0.1928    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566    1.3635   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.7694    0.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.4315    1.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0364   -1.5907    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4341   -2.6953    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3393   -1.5459    2.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    0.3001   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876    1.3872    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    1.4314    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    0.1053    0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -0.2154    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070   -0.8186   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1905   -0.9258   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.2158   -0.5525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0361    1.5324   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -0.4871   -0.3216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1316    0.2278   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059   -1.7609   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9314   -1.6957    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.4439    0.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8140   -0.5379    1.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459    0.7339    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7726   -0.5167   -2.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3216    1.6054   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705    1.8561   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519    1.2304   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8886   -1.0408   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3824    1.0822    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3010    1.5304    2.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4392   -0.6379    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720   -1.0328    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6592    2.3464   -0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114    1.3762   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.8918   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.2110   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3849   -2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903    0.3747   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0717   -2.6009   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4363   -0.3484    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 74  1  1
 32 75  1  0
M  END


  Mrv0541 02231220552D          

 32 35  0  0  1  0            999 V2000
   17.8568  -12.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8669  -13.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1547  -12.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4978  -11.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2798  -13.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7949  -14.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6908  -11.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4379  -14.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5813  -13.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1524  -14.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2958  -12.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1524  -15.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3318  -11.4524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7234  -15.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0102  -15.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7179  -11.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 25  2  1  1  0  0  0
 26  3  1  1  0  0  0
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 22 30  2  0  0  0  0
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 23 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006898

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC(=O)NCC(O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15?,16?,17-,18?,19?,20?,21-,24?,25+,26-/m1/s1

> <INCHI_KEY>
GHCZAUBVMUEKKP-AFQLCFGXSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.805215356559074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido}acetic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.608022284

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.791653018199973

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.773307537576899

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2921848801328769

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
122.07729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006898
     RDKit          3D
Chenodeoxyglycocholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.7180   -0.4015   -2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.6896   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720    0.9719   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -0.2341   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    0.1928    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566    1.3635   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.7694    0.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.4315    1.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0364   -1.5907    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4341   -2.6953    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3393   -1.5459    2.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    0.3001   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876    1.3872    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    1.4314    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    0.1053    0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -0.2154    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070   -0.8186   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024   -0.6773   -1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -0.9258   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.2158   -0.5525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0361    1.5324   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -0.4871   -0.3216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1316    0.2278   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059   -1.7609   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9314   -1.6957    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.4439    0.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8140   -0.5379    1.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459    0.7339    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    0.3073    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.5011    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3749    0.8968    1.7639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0028    0.4441    2.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -0.5167   -2.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -1.3963   -1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.1381   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216    1.6054   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705    1.8561   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519    1.2304   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1987   -0.6702    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -1.0408   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -1.7475    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -0.0148    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2821    0.3817    1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0778   -1.0442    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081   -0.6517    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    1.0822    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0466    2.3491    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    1.5304    2.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    2.3090    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.6379    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720   -1.0328    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.9546   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525    0.2989   -1.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -1.4471   -2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -1.0631   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090   -1.8822   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    2.3464   -0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114    1.3762   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.8918   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.2110   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3849   -2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903    0.3747   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9398   -2.0384   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0717   -2.6009   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5866   -2.5349    0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7641   -1.8740    1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063   -0.3380   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4308    0.2415    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9512    1.5566   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2228    1.1665    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363   -0.3484    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928    2.2380    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2260    1.9869    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891    1.6670    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5280   -0.4121    3.1759 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 17 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 20 12  1  0
 29 22  1  0
 20 15  1  0
 31 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  6
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 31 74  1  1
 32 75  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      33.333 -22.706   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.885 -25.737   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.155 -23.451   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.796 -21.882   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.256 -25.737   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.350 -26.983   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.289 -22.202   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.217 -27.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.218 -24.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.551 -26.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.552 -24.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.551 -29.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.218 -29.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.277 -22.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.826 -23.026   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.885 -28.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.217 -28.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.350 -24.491   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.886 -26.507   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.218 -26.507   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.552 -28.817   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.259 -21.058   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.770 -23.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      28.552 -27.277   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.885 -27.277   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.886 -24.967   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      26.753 -21.378   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      21.884 -29.587   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      29.886 -29.587   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      28.735 -19.593   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      23.740 -22.018   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      24.294 -24.627   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   15    7                                                       
CONECT    5   18    6                                                       
CONECT    6    5   19                                                       
CONECT    7    4   22                                                       
CONECT    8   10   17                                                       
CONECT    9   20   11                                                       
CONECT   10    8   25                                                       
CONECT   11    9   26                                                       
CONECT   12   17   16                                                       
CONECT   13   16   21                                                       
CONECT   14   27   23                                                       
CONECT   15    1    4   18                                                  
CONECT   16   12   13   25                                                  
CONECT   17    8   12   28                                                  
CONECT   18    5   15   26                                                  
CONECT   19    6   24   26                                                  
CONECT   20    9   24   25                                                  
CONECT   21   13   24   29                                                  
CONECT   22    7   30   27                                                  
CONECT   23   14   31   32                                                  
CONECT   24   19   20   21                                                  
CONECT   25    2   10   16   20                                             
CONECT   26    3   11   18   19                                             
CONECT   27   14   22                                                       
CONECT   28   17                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32   23                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0006898
HETATM    1  C1  UNL     1       2.718  -0.401  -2.367  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.664   0.690  -1.323  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.072   0.972  -0.885  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.763  -0.234  -0.288  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.134   0.193   0.095  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.557   1.364  -0.085  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.993  -0.769   0.686  1.00  0.00           N  
HETATM    8  C6  UNL     1       8.343  -0.431   1.086  1.00  0.00           C  
HETATM    9  C7  UNL     1       9.036  -1.591   1.673  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.434  -2.695   1.768  1.00  0.00           O  
HETATM   11  O3  UNL     1      10.339  -1.546   2.140  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.755   0.300  -0.218  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.688   1.387   0.873  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.244   1.431   1.351  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.249   0.105   0.858  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.673  -0.215   1.024  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.407  -0.819  -0.117  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.702  -0.677  -1.452  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.191  -0.926  -1.309  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.297   0.216  -0.553  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.036   1.532  -1.205  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.841  -0.487  -0.322  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.132   0.228  -1.618  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.706  -1.761  -0.415  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.931  -1.696   0.426  1.00  0.00           C  
HETATM   26  C22 UNL     1      -6.737  -0.444   0.248  1.00  0.00           C  
HETATM   27  O4  UNL     1      -7.814  -0.538   1.162  1.00  0.00           O  
HETATM   28  C23 UNL     1      -5.846   0.734   0.571  1.00  0.00           C  
HETATM   29  C24 UNL     1      -4.443   0.307   0.790  1.00  0.00           C  
HETATM   30  C25 UNL     1      -3.537   1.501   0.986  1.00  0.00           C  
HETATM   31  C26 UNL     1      -2.375   0.897   1.764  1.00  0.00           C  
HETATM   32  O5  UNL     1      -3.003   0.444   2.955  1.00  0.00           O  
HETATM   33  H1  UNL     1       3.773  -0.517  -2.766  1.00  0.00           H  
HETATM   34  H2  UNL     1       2.481  -1.396  -1.957  1.00  0.00           H  
HETATM   35  H3  UNL     1       2.135  -0.138  -3.287  1.00  0.00           H  
HETATM   36  H4  UNL     1       2.322   1.605  -1.861  1.00  0.00           H  
HETATM   37  H5  UNL     1       4.170   1.856  -0.225  1.00  0.00           H  
HETATM   38  H6  UNL     1       4.652   1.230  -1.815  1.00  0.00           H  
HETATM   39  H7  UNL     1       4.199  -0.670   0.556  1.00  0.00           H  
HETATM   40  H8  UNL     1       4.889  -1.041  -1.039  1.00  0.00           H  
HETATM   41  H9  UNL     1       6.673  -1.748   0.849  1.00  0.00           H  
HETATM   42  H10 UNL     1       8.865  -0.015   0.192  1.00  0.00           H  
HETATM   43  H11 UNL     1       8.282   0.382   1.852  1.00  0.00           H  
HETATM   44  H12 UNL     1      11.078  -1.044   1.679  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.108  -0.652   0.220  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.382   1.082   1.709  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.047   2.349   0.519  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.301   1.530   2.444  1.00  0.00           H  
HETATM   49  H17 UNL     1      -0.237   2.309   0.857  1.00  0.00           H  
HETATM   50  H18 UNL     1       0.439  -0.638   1.370  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.672  -1.033   1.831  1.00  0.00           H  
HETATM   52  H20 UNL     1      -2.415  -1.955  -0.004  1.00  0.00           H  
HETATM   53  H21 UNL     1      -1.853   0.299  -1.939  1.00  0.00           H  
HETATM   54  H22 UNL     1      -2.043  -1.447  -2.183  1.00  0.00           H  
HETATM   55  H23 UNL     1       0.162  -1.063  -2.344  1.00  0.00           H  
HETATM   56  H24 UNL     1      -0.109  -1.882  -0.754  1.00  0.00           H  
HETATM   57  H25 UNL     1       0.659   2.346  -0.972  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.011   1.376  -2.303  1.00  0.00           H  
HETATM   59  H27 UNL     1      -1.065   1.892  -0.960  1.00  0.00           H  
HETATM   60  H28 UNL     1      -3.641   1.211  -1.725  1.00  0.00           H  
HETATM   61  H29 UNL     1      -3.748  -0.385  -2.485  1.00  0.00           H  
HETATM   62  H30 UNL     1      -5.190   0.375  -1.805  1.00  0.00           H  
HETATM   63  H31 UNL     1      -4.940  -2.038  -1.438  1.00  0.00           H  
HETATM   64  H32 UNL     1      -4.072  -2.601  -0.003  1.00  0.00           H  
HETATM   65  H33 UNL     1      -6.587  -2.535   0.100  1.00  0.00           H  
HETATM   66  H34 UNL     1      -5.764  -1.874   1.509  1.00  0.00           H  
HETATM   67  H35 UNL     1      -7.206  -0.338  -0.735  1.00  0.00           H  
HETATM   68  H36 UNL     1      -8.431   0.241   1.034  1.00  0.00           H  
HETATM   69  H37 UNL     1      -5.951   1.557  -0.184  1.00  0.00           H  
HETATM   70  H38 UNL     1      -6.223   1.167   1.522  1.00  0.00           H  
HETATM   71  H39 UNL     1      -4.436  -0.348   1.694  1.00  0.00           H  
HETATM   72  H40 UNL     1      -3.993   2.238   1.682  1.00  0.00           H  
HETATM   73  H41 UNL     1      -3.226   1.987   0.072  1.00  0.00           H  
HETATM   74  H42 UNL     1      -1.689   1.667   2.107  1.00  0.00           H  
HETATM   75  H43 UNL     1      -2.528  -0.412   3.176  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   12   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6    6    7
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   11
CONECT   11   44
CONECT   12   13   20   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   20   50
CONECT   16   17   31   51
CONECT   17   18   22   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21
CONECT   21   57   58   59
CONECT   22   23   24   29
CONECT   23   60   61   62
CONECT   24   25   63   64
CONECT   25   26   65   66
CONECT   26   27   28   67
CONECT   27   68
CONECT   28   29   69   70
CONECT   29   30   71
CONECT   30   31   72   73
CONECT   31   32   74
CONECT   32   75
END

HMDB0006898
     RDKit          3D
Chenodeoxyglycocholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.7180   -0.4015   -2.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6638    0.6896   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0720    0.9719   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630   -0.2341   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    0.1928    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566    1.3635   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9929   -0.7694    0.6864 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3426   -0.4315    1.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0364   -1.5907    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4341   -2.6953    1.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3393   -1.5459    2.1403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547    0.3001   -0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876    1.3872    0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    1.4314    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    0.1053    0.8577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6726   -0.2154    1.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4070   -0.8186   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024   -0.6773   -1.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905   -0.9258   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966    0.2158   -0.5525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0361    1.5324   -1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -0.4871   -0.3216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1316    0.2278   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7059   -1.7609   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9314   -1.6957    0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7374   -0.4439    0.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8140   -0.5379    1.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8459    0.7339    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4428    0.3073    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.5011    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3749    0.8968    1.7639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0028    0.4441    2.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -0.5167   -2.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806   -1.3963   -1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.1381   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3216    1.6054   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705    1.8561   -0.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519    1.2304   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1987   -0.6702    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -1.0408   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -1.7475    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8646   -0.0148    0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2821    0.3817    1.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0778   -1.0442    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1081   -0.6517    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    1.0822    1.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0466    2.3491    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    1.5304    2.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    2.3090    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.6379    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6720   -1.0328    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -1.9546   -0.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525    0.2989   -1.9392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -1.4471   -2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -1.0631   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090   -1.8822   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6592    2.3464   -0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0114    1.3762   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653    1.8918   -0.9603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6415    1.2110   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7478   -0.3849   -2.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903    0.3747   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9398   -2.0384   -1.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0717   -2.6009   -0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5866   -2.5349    0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7641   -1.8740    1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2063   -0.3380   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4308    0.2415    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9512    1.5566   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2228    1.1665    1.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363   -0.3484    1.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928    2.2380    1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2260    1.9869    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891    1.6670    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5280   -0.4121    3.1759 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
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 17 22  1  0
 22 23  1  6
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 20 12  1  0
 29 22  1  0
 20 15  1  0
 31 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 26 67  1  6
 27 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 31 74  1  1
 32 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chenodeoxyglycocholate	Generator
2-({4-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-1-hydroxypentylidene}amino)acetate	Generator

Chemical Formula

C₂₆H₄₃NO₅

Average Molecular Weight

449.6233

Monoisotopic Molecular Weight

449.314123491

IUPAC Name

2-{4-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido}acetic acid

Traditional Name

{4-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido}acetic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(=O)NCC(O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15?,16?,17-,18?,19?,20?,21-,24?,25+,26-/m1/s1

InChI Key

GHCZAUBVMUEKKP-AFQLCFGXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0006898)
Cell membrane (HMDB: HMDB0006898)

Biofluid or Excreta

Urine (HMDB: HMDB0006898)

Tissue substructure

Hepatic tissue (HMDB: HMDB0006898)

Cellular substructure

Extracellular (HMDB: HMDB0006898)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006898)

Source

Endogenous

Endogenous (HMDB: HMDB0006898)

Animal

Animal (HMDB: HMDB0006898)

Exogenous

Food

Food (HMDB: HMDB0006898)

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: HMDB0006898)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006898)

Cellular process

Cell signaling (HMDB: HMDB0006898)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0006898)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006898)

Molecular messenger

Signaling molecule (HMDB: HMDB0006898)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006898)

Emulsifier (HMDB: HMDB0006898)

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	0.0079 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.08 m³·mol⁻¹	ChemAxon
Polarizability	51.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	200.594	31661259
DarkChem	[M-H]-	192.968	31661259
DeepCCS	[M-2H]-	238.039	30932474
DeepCCS	[M+Na]+	213.464	30932474
AllCCS	[M+H]+	212.4	32859911
AllCCS	[M+H-H2O]+	210.6	32859911
AllCCS	[M+NH4]+	214.0	32859911
AllCCS	[M+Na]+	214.4	32859911
AllCCS	[M-H]-	205.3	32859911
AllCCS	[M+Na-2H]-	207.3	32859911
AllCCS	[M+HCOO]-	209.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxyglycocholic acid	CC(CCC(=O)NCC(O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C	3363.0	Standard polar	33892256
Chenodeoxyglycocholic acid	CC(CCC(=O)NCC(O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C	3297.8	Standard non polar	33892256
Chenodeoxyglycocholic acid	CC(CCC(=O)NCC(O)=O)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C	4103.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chenodeoxyglycocholic acid,1TMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	3962.2	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TMS,isomer #2	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C	3968.8	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TMS,isomer #3	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O	3976.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TMS,isomer #4	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	3943.4	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O	3915.2	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #2	CC(CCC(=O)NCC(=O)O[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C	3887.8	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #3	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	3900.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #4	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	3944.7	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #5	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C	3897.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TMS,isomer #6	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O	3943.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	3819.9	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TMS,isomer #2	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O	3852.9	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TMS,isomer #3	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C	3810.8	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TMS,isomer #4	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	3835.9	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,4TMS,isomer #1	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	3747.0	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,4TMS,isomer #1	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	3793.8	Standard non polar	33892256
Chenodeoxyglycocholic acid,4TMS,isomer #1	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)CC1C[C@H]3O[Si](C)(C)C	4078.2	Standard polar	33892256
Chenodeoxyglycocholic acid,1TBDMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	4187.9	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TBDMS,isomer #2	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4169.8	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TBDMS,isomer #3	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O	4195.2	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,1TBDMS,isomer #4	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	4160.6	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O	4358.5	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #2	CC(CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4275.0	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #3	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O	4362.9	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #4	CC(CCC(=O)NCC(=O)O)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4349.5	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #5	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4336.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,2TBDMS,isomer #6	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O	4396.5	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TBDMS,isomer #1	CC(CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4426.2	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TBDMS,isomer #2	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O	4546.0	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TBDMS,isomer #3	CC(CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4473.1	Semi standard non polar	33892256
Chenodeoxyglycocholic acid,3TBDMS,isomer #4	CC(CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)C1CCC2C3C(CC[C@]12C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)CC1C[C@H]3O[Si](C)(C)C(C)(C)C	4511.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxyglycocholic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-003u-1223900000-3350cb54efde717c988c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxyglycocholic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-1001029000-2c90d59630fb6b214a2e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chenodeoxyglycocholic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Chenodeoxyglycocholic acid 10V, Positive-QTOF	splash10-0gz9-2002900000-3abffd226605ac6cf9ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 20V, Positive-QTOF	splash10-056r-9005400000-e6ffe50d890cb63a4461	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 40V, Positive-QTOF	splash10-004i-9105200000-f81ed28d5795157627cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 10V, Negative-QTOF	splash10-0002-0000900000-9e4d382267acd7d0da8c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 20V, Negative-QTOF	splash10-00ea-4103900000-d0ad37cdb8c4ebcc8b3f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 40V, Negative-QTOF	splash10-05fr-9001000000-146adacced28077cba6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 10V, Negative-QTOF	splash10-0002-0000900000-9c8720c88dcc5ed55fa7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 20V, Negative-QTOF	splash10-000t-1001900000-2bc798e522a0b6147a61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 40V, Negative-QTOF	splash10-05fr-9003100000-93b7723cdc53cd4e35ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 10V, Positive-QTOF	splash10-0ue9-0000900000-2a4d946db77fcfab0e9c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 20V, Positive-QTOF	splash10-08gv-4319600000-48d6b0bd21595df5aa8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chenodeoxyglycocholic acid 40V, Positive-QTOF	splash10-066s-9142000000-337965ce39e2ae3f0648	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

FDB024145

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05462

BioCyc ID

Not Available

BiGG ID

45858

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477907

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

2. 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 Chenodeoxyglycocholic acid (HMDB0006898)

MOL for HMDB0006898 (Chenodeoxyglycocholic acid)

3D MOL for HMDB0006898 (Chenodeoxyglycocholic acid)

3D SDF for HMDB0006898 (Chenodeoxyglycocholic acid)

3D-SDF for HMDB0006898 (Chenodeoxyglycocholic acid)

PDB for HMDB0006898 (Chenodeoxyglycocholic acid)

3D PDB for HMDB0006898 (Chenodeoxyglycocholic acid)

SMILES for HMDB0006898 (Chenodeoxyglycocholic acid)

INCHI for HMDB0006898 (Chenodeoxyglycocholic acid)

Structure for HMDB0006898 (Chenodeoxyglycocholic acid)

3D Structure for HMDB0006898 (Chenodeoxyglycocholic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References