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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (8) Show 11 proteins XML

enzymes (3)transporters (8) Show 11 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:19:05 UTC

HMDB ID

HMDB0000601

Secondary Accession Numbers

HMDB0003873
HMDB00601
HMDB03873

Metabolite Identification

Common Name

Coprocholic acid

Description

Coprocholic acid, also called 3α,7α,12α-Trihydroxy-5β-cholestan-26-oic acid, is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and the 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 SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305231918412D          

 37 40  0  0  0  0            999 V2000
 9999.6406 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.638510001.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3579 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9997.3127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9999.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2131 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925710001.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6385 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9257 9999.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.9081 9999.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4231 9999.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.423110000.4698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.423110001.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.138710001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.852310001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567910001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.712810001.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210002.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610000.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.709010001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.138710000.8822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7855 9999.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7855 9997.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5000 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5000 9998.9670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9999.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9997.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9272 9998.1432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9272 9998.9683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.925710000.6272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.211210000.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6402 9999.3896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.640210000.2147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  6  0  0  0
 13 14  1  0  0  0  0
 13 22  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 12  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 34  7  1  6  0  0  0
 36 11  1  0  0  0  0
 12 37  1  0  0  0  0
 37  2  1  1  0  0  0
 36  8  1  6  0  0  0
 32  1  1  6  0  0  0
 35 30  1  0  0  0  0
 33 36  1  0  0  0  0
 30  6  1  6  0  0  0
 33  9  1  1  0  0  0
 26  3  1  6  0  0  0
 30 29  1  0  0  0  0
 28 31  1  0  0  0  0
 28  4  1  1  0  0  0
 29  5  1  1  0  0  0
M  END


  Mrv1652305231918412D          

 37 40  0  0  0  0            999 V2000
 9999.6406 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.638510001.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3579 9997.7263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9997.3127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5003 9999.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2131 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925710001.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6385 9998.5598    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9257 9999.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.9081 9999.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4231 9999.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.423110000.4698    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.423110001.2948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.138710001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.852310001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.567910001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610001.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.712810001.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.997210002.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.281610000.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.709010001.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.138710000.8822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7855 9999.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0710 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.7855 9997.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5000 9998.1419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5000 9998.9670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9999.3808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2127 9997.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9272 9998.1432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9272 9998.9683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.925710000.6272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.211210000.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6402 9999.3896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.640210000.2147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 23  1  6  0  0  0
 13 14  1  0  0  0  0
 13 22  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 10 12  1  0  0  0  0
 24 25  1  0  0  0  0
 24 29  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  1  0  0  0  0
 36 37  1  0  0  0  0
 34  7  1  6  0  0  0
 36 11  1  0  0  0  0
 12 37  1  0  0  0  0
 37  2  1  1  0  0  0
 36  8  1  6  0  0  0
 32  1  1  6  0  0  0
 35 30  1  0  0  0  0
 33 36  1  0  0  0  0
 30  6  1  6  0  0  0
 33  9  1  1  0  0  0
 26  3  1  6  0  0  0
 30 29  1  0  0  0  0
 28 31  1  0  0  0  0
 28  4  1  1  0  0  0
 29  5  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000601

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

> <INCHI_KEY>
CNWPIIOQKZNXBB-VCVMUKOKSA-N

> <FORMULA>
C27H46O5

> <MOLECULAR_WEIGHT>
450.6511

> <EXACT_MASS>
450.334524582

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.32339719269413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.9146180650000013

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.2963399055959

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.618758291832509

> <JCHEM_PKA_STRONGEST_BASIC>
-0.15944064032502225

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
124.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:77})
 78 81  0  0  0  0  0  0  0  0999 V2000
   -1.1584   -0.3942   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1538    0.1134   -0.6917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1750    1.6491   -0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698    2.1835   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    0.9609   -0.4190 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4014    0.7955   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954    0.9708    0.5017 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9673    1.0635    1.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2254    2.1326    0.1486 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6982    3.0761    0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6362    2.0167   -1.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560    2.0943    1.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1975    0.7707    0.8593 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0721    0.7434    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6418    0.6486   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3840   -0.6744   -0.7985 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2593   -0.7010   -0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7980   -0.7882   -2.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543   -1.8383   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0098   -1.7160    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665   -0.3933    1.2073 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8184   -0.2719    2.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0293   -0.3653    0.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3488   -0.4267   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -1.5665    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -1.5179   -0.2126 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1971   -2.3560    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406   -1.5709   -1.6083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451   -0.1777    0.0525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0590    0.0100    1.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3565   -0.3285    0.1446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3465    0.1953    1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816   -1.8370    0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6484    0.0032   -0.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -0.3236    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1431    0.0080   -0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3459   -0.3187    0.4197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3412    0.5994    1.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6177   -0.1086   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8066   -0.3357    0.2193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5673    0.2642   -1.5091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    1.8864   -1.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103    2.0866   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498    2.9986   -0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537    2.5029    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292    2.7219   -1.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1186    2.9227    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423    2.1828    2.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669    0.6755   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3043    1.4777   -0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2760   -1.6049   -2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5795   -1.8122   -1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9835   -2.7809   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4484    1.0098    1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6999   -0.5882   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8394   -1.3840    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    0.2678    1.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1549    1.0684   -0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1946   -0.5833   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2863   -1.3575    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1981    0.3667    2.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4213    0.4474    2.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4009    1.6381    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5945   -0.1871   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 29  1  0  0  0  0
  2 31  1  0  0  0  0
  3  4  1  0  0  0  0
  3 42  1  0  0  0  0
  3 43  1  0  0  0  0
  4  5  1  0  0  0  0
  4 44  1  0  0  0  0
  4 45  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 29  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 23  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 11 46  1  0  0  0  0
 12 13  1  0  0  0  0
 12 47  1  0  0  0  0
 12 48  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 13 21  1  0  0  0  0
 15 16  1  0  0  0  0
 15 49  1  0  0  0  0
 15 50  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 51  1  0  0  0  0
 19 20  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 20 21  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 59  1  0  0  0  0
 25 60  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 61  1  0  0  0  0
 29 30  1  1  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 30 64  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 33 65  1  0  0  0  0
 33 66  1  0  0  0  0
 33 67  1  0  0  0  0
 34 35  1  0  0  0  0
 34 68  1  0  0  0  0
 34 69  1  0  0  0  0
 35 36  1  0  0  0  0
 35 70  1  0  0  0  0
 35 71  1  0  0  0  0
 36 37  1  0  0  0  0
 36 72  1  0  0  0  0
 36 73  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 74  1  1  0  0  0
 38 75  1  0  0  0  0
 38 76  1  0  0  0  0
 38 77  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 40 78  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 23-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAY-19         0                                  
HETATM    1  O   UNK     0    8665.9968662.422   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.9928668.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0018662.422   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.0018661.650   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8662.0018666.284   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8663.3318663.978   0.000  0.00  0.00           H+0
HETATM    7  O   UNK     0    8664.6618669.391   0.000  0.00  0.00           O+0
HETATM    8  H   UNK     0    8665.9928663.978   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8664.6618666.284   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8668.3628666.298   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.4568665.052   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.4568667.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.4568669.084   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.7928669.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.1248669.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8671.4608669.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8672.7928669.084   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8674.1288669.853   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8675.4648669.084   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8674.1288671.393   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8672.7928667.544   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.1238669.853   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0    8668.7928668.313   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0    8660.6668665.508   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8659.3338664.738   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8659.3338663.198   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8660.6668662.428   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8662.0008663.198   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8662.0008664.738   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8663.3308665.511   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8663.3308662.431   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8664.6648663.201   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8664.6648664.741   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8664.6618667.837   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8663.3288667.067   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8665.9958665.527   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8665.9958667.067   0.000  0.00  0.00           C+0
CONECT    1   32                                                            
CONECT    2   37                                                            
CONECT    3   26                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   34                                                            
CONECT    8   36                                                            
CONECT    9   33                                                            
CONECT   10   11   12                                                       
CONECT   11   10   36                                                       
CONECT   12   13   23   10   37                                             
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   13                                                            
CONECT   23   12                                                            
CONECT   24   25   29                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27    3                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31    4                                             
CONECT   29   24   28   30    5                                             
CONECT   30   33   35    6   29                                             
CONECT   31   32   28                                                       
CONECT   32   31   33    1                                                  
CONECT   33   30   32   36    9                                             
CONECT   34   35   37    7                                                  
CONECT   35   34   30                                                       
CONECT   36   37   11    8   33                                             
CONECT   37   34   36   12    2                                             
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -1.158  -0.394  -1.656  1.00  0.00           H  
HETATM    2  C   UNL     1      -1.154   0.113  -0.692  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.175   1.649  -0.893  1.00  0.00           C  
HETATM    4  C   UNL     1       0.170   2.183  -0.329  1.00  0.00           C  
HETATM    5  C   UNL     1       1.090   0.961  -0.419  1.00  0.00           C  
HETATM    6  H   UNL     1       1.401   0.795  -1.450  1.00  0.00           H  
HETATM    7  C   UNL     1       2.295   0.971   0.502  1.00  0.00           C  
HETATM    8  H   UNL     1       1.967   1.063   1.537  1.00  0.00           H  
HETATM    9  C   UNL     1       3.225   2.133   0.149  1.00  0.00           C  
HETATM   10  H   UNL     1       2.698   3.076   0.290  1.00  0.00           H  
HETATM   11  O   UNL     1       3.636   2.017  -1.215  1.00  0.00           O  
HETATM   12  C   UNL     1       4.456   2.094   1.057  1.00  0.00           C  
HETATM   13  C   UNL     1       5.197   0.771   0.859  1.00  0.00           C  
HETATM   14  H   UNL     1       6.072   0.743   1.509  1.00  0.00           H  
HETATM   15  C   UNL     1       5.642   0.649  -0.600  1.00  0.00           C  
HETATM   16  C   UNL     1       6.384  -0.674  -0.798  1.00  0.00           C  
HETATM   17  H   UNL     1       7.259  -0.701  -0.149  1.00  0.00           H  
HETATM   18  O   UNL     1       6.798  -0.788  -2.162  1.00  0.00           O  
HETATM   19  C   UNL     1       5.454  -1.838  -0.449  1.00  0.00           C  
HETATM   20  C   UNL     1       5.010  -1.716   1.010  1.00  0.00           C  
HETATM   21  C   UNL     1       4.266  -0.393   1.207  1.00  0.00           C  
HETATM   22  C   UNL     1       3.818  -0.272   2.665  1.00  0.00           C  
HETATM   23  C   UNL     1       3.029  -0.365   0.307  1.00  0.00           C  
HETATM   24  H   UNL     1       3.349  -0.427  -0.733  1.00  0.00           H  
HETATM   25  C   UNL     1       2.139  -1.567   0.607  1.00  0.00           C  
HETATM   26  C   UNL     1       0.839  -1.518  -0.213  1.00  0.00           C  
HETATM   27  H   UNL     1       0.197  -2.356   0.060  1.00  0.00           H  
HETATM   28  O   UNL     1       1.141  -1.571  -1.608  1.00  0.00           O  
HETATM   29  C   UNL     1       0.145  -0.178   0.052  1.00  0.00           C  
HETATM   30  C   UNL     1      -0.059   0.010   1.557  1.00  0.00           C  
HETATM   31  C   UNL     1      -2.357  -0.329   0.145  1.00  0.00           C  
HETATM   32  H   UNL     1      -2.346   0.195   1.101  1.00  0.00           H  
HETATM   33  C   UNL     1      -2.282  -1.837   0.389  1.00  0.00           C  
HETATM   34  C   UNL     1      -3.648   0.003  -0.605  1.00  0.00           C  
HETATM   35  C   UNL     1      -4.851  -0.324   0.282  1.00  0.00           C  
HETATM   36  C   UNL     1      -6.143   0.008  -0.468  1.00  0.00           C  
HETATM   37  C   UNL     1      -7.346  -0.319   0.420  1.00  0.00           C  
HETATM   38  C   UNL     1      -7.341   0.599   1.644  1.00  0.00           C  
HETATM   39  C   UNL     1      -8.618  -0.109  -0.361  1.00  0.00           C  
HETATM   40  O   UNL     1      -9.807  -0.336   0.219  1.00  0.00           O  
HETATM   41  O   UNL     1      -8.567   0.264  -1.509  1.00  0.00           O  
HETATM   42  H   UNL     1      -1.256   1.886  -1.954  1.00  0.00           H  
HETATM   43  H   UNL     1      -2.010   2.087  -0.346  1.00  0.00           H  
HETATM   44  H   UNL     1       0.550   2.999  -0.944  1.00  0.00           H  
HETATM   45  H   UNL     1       0.054   2.503   0.707  1.00  0.00           H  
HETATM   46  H   UNL     1       4.229   2.722  -1.509  1.00  0.00           H  
HETATM   47  H   UNL     1       5.119   2.923   0.806  1.00  0.00           H  
HETATM   48  H   UNL     1       4.142   2.183   2.097  1.00  0.00           H  
HETATM   49  H   UNL     1       4.767   0.675  -1.249  1.00  0.00           H  
HETATM   50  H   UNL     1       6.304   1.478  -0.848  1.00  0.00           H  
HETATM   51  H   UNL     1       7.276  -1.605  -2.361  1.00  0.00           H  
HETATM   52  H   UNL     1       4.580  -1.812  -1.099  1.00  0.00           H  
HETATM   53  H   UNL     1       5.984  -2.781  -0.590  1.00  0.00           H  
HETATM   54  H   UNL     1       4.348  -2.545   1.259  1.00  0.00           H  
HETATM   55  H   UNL     1       5.885  -1.741   1.660  1.00  0.00           H  
HETATM   56  H   UNL     1       4.692  -0.298   3.317  1.00  0.00           H  
HETATM   57  H   UNL     1       3.289   0.671   2.805  1.00  0.00           H  
HETATM   58  H   UNL     1       3.155  -1.101   2.912  1.00  0.00           H  
HETATM   59  H   UNL     1       2.680  -2.481   0.363  1.00  0.00           H  
HETATM   60  H   UNL     1       1.892  -1.572   1.668  1.00  0.00           H  
HETATM   61  H   UNL     1       1.614  -2.370  -1.878  1.00  0.00           H  
HETATM   62  H   UNL     1       0.894  -0.114   2.071  1.00  0.00           H  
HETATM   63  H   UNL     1      -0.448   1.010   1.749  1.00  0.00           H  
HETATM   64  H   UNL     1      -0.768  -0.733   1.923  1.00  0.00           H  
HETATM   65  H   UNL     1      -1.361  -2.073   0.923  1.00  0.00           H  
HETATM   66  H   UNL     1      -3.138  -2.152   0.985  1.00  0.00           H  
HETATM   67  H   UNL     1      -2.292  -2.361  -0.567  1.00  0.00           H  
HETATM   68  H   UNL     1      -3.660   1.064  -0.857  1.00  0.00           H  
HETATM   69  H   UNL     1      -3.700  -0.588  -1.519  1.00  0.00           H  
HETATM   70  H   UNL     1      -4.839  -1.384   0.534  1.00  0.00           H  
HETATM   71  H   UNL     1      -4.800   0.268   1.196  1.00  0.00           H  
HETATM   72  H   UNL     1      -6.155   1.068  -0.720  1.00  0.00           H  
HETATM   73  H   UNL     1      -6.195  -0.583  -1.382  1.00  0.00           H  
HETATM   74  H   UNL     1      -7.286  -1.357   0.745  1.00  0.00           H  
HETATM   75  H   UNL     1      -8.198   0.367   2.276  1.00  0.00           H  
HETATM   76  H   UNL     1      -6.421   0.447   2.208  1.00  0.00           H  
HETATM   77  H   UNL     1      -7.401   1.638   1.319  1.00  0.00           H  
HETATM   78  H   UNL     1     -10.595  -0.187  -0.321  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3   29   31                                       
CONECT    3    2    4   42   43                                       
CONECT    4    3    5   44   45                                       
CONECT    5    4    6    7   29                                       
CONECT    6    5                                                      
CONECT    7    5    8    9   23                                       
CONECT    8    7                                                      
CONECT    9    7   10   11   12                                       
CONECT   10    9                                                      
CONECT   11    9   46                                                 
CONECT   12    9   13   47   48                                       
CONECT   13   12   14   15   21                                       
CONECT   14   13                                                      
CONECT   15   13   16   49   50                                       
CONECT   16   15   17   18   19                                       
CONECT   17   16                                                      
CONECT   18   16   51                                                 
CONECT   19   16   20   52   53                                       
CONECT   20   19   21   54   55                                       
CONECT   21   20   13   22   23                                       
CONECT   22   21   56   57   58                                       
CONECT   23   21    7   24   25                                       
CONECT   24   23                                                      
CONECT   25   23   26   59   60                                       
CONECT   26   25   27   28   29                                       
CONECT   27   26                                                      
CONECT   28   26   61                                                 
CONECT   29   26    2    5   30                                       
CONECT   30   29   62   63   64                                       
CONECT   31    2   32   33   34                                       
CONECT   32   31                                                      
CONECT   33   31   65   66   67                                       
CONECT   34   31   35   68   69                                       
CONECT   35   34   36   70   71                                       
CONECT   36   35   37   72   73                                       
CONECT   37   36   38   39   74                                       
CONECT   38   37   75   76   77                                       
CONECT   39   37   40   41   41                                       
CONECT   40   39   78                                                 
CONECT   41   39   39                                                 
CONECT   42    3                                                      
CONECT   43    3                                                      
CONECT   44    4                                                      
CONECT   45    4                                                      
CONECT   46   11                                                      
CONECT   47   12                                                      
CONECT   48   12                                                      
CONECT   49   15                                                      
CONECT   50   15                                                      
CONECT   51   18                                                      
CONECT   52   19                                                      
CONECT   53   19                                                      
CONECT   54   20                                                      
CONECT   55   20                                                      
CONECT   56   22                                                      
CONECT   57   22                                                      
CONECT   58   22                                                      
CONECT   59   25                                                      
CONECT   60   25                                                      
CONECT   61   28                                                      
CONECT   62   30                                                      
CONECT   63   30                                                      
CONECT   64   30                                                      
CONECT   65   33                                                      
CONECT   66   33                                                      
CONECT   67   33                                                      
CONECT   68   34                                                      
CONECT   69   34                                                      
CONECT   70   35                                                      
CONECT   71   35                                                      
CONECT   72   36                                                      
CONECT   73   36                                                      
CONECT   74   37                                                      
CONECT   75   38                                                      
CONECT   76   38                                                      
CONECT   77   38                                                      
CONECT   78   40                                                      
MASTER        0    0    0    0    0    0    0    0   78    0   78    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D1(CC%5BC@@%5D2(...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:77})
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oic acid	ChEBI
3,7,12-Trihydroxycholestan-26-Oic acid	ChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oic acid	Generator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oate	Generator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oic acid	Generator
3,7,12-Trihydroxycholestan-26-Oate	Generator
Coprocholate	Generator
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oate	HMDB
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-Oate	HMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-Oic acid	HMDB
3a,7a,12a-Trihydroxycoprostanate	HMDB
3a,7a,12a-Trihydroxycoprostanic acid	HMDB
5b-Cholestane-3a,7a,12a-triol-26-Oate	HMDB
5b-Cholestane-3a,7a,12a-triol-26-Oic acid	HMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5-beta-cholestan-26-Oic acid	HMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25R)-isomer	HMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25S)-isomer	HMDB
3Α,7α,12α-trihydroxy-5β-cholestan-26-Oic acid	HMDB
3Α,7α,12α-trihydroxycoprostanic acid	HMDB
5Β-cholestane-3α,7α,12α-triol-26-Oic acid	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oic acid	HMDB
3alpha,7alpha,12alpha-Trihydroxycoprostanic acid	HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-Oic acid	HMDB
Trihydroxycoprostanic acid	HMDB
Trihydroxycoprostanoic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestanoic acid	HMDB
3a,7a,12a-Trihydroxy-5b-cholestanoate	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate	HMDB
3Α,7α,12α-trihydroxy-5β-cholestanoate	HMDB
3Α,7α,12α-trihydroxy-5β-cholestanoic acid	HMDB
Coprocholic acid	HMDB, ChEBI

Chemical Formula

C₂₇H₄₆O₅

Average Molecular Weight

450.6511

Monoisotopic Molecular Weight

450.334524582

IUPAC Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

Traditional Name

(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid

CAS Registry Number

547-98-8

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O

InChI Identifier

InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1

InChI Key

CNWPIIOQKZNXBB-VCVMUKOKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
12-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:18402 )
hydroxy monocarboxylic acid (CHEBI:18402 )
7alpha-hydroxy steroid (CHEBI:18402 )
12alpha-hydroxy steroid (CHEBI:18402 )
steroid acid (CHEBI:18402 )
C27 bile acids, alcohols, and derivatives (LMST04030001 )

Ontology

Physiological effect

Health effect:

Health condition:

Refsum's disease

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Subcellular:

Organ and components:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.91	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.16	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	53.32 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

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0353900000-c3bc744526d90b133841	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-1341349000-6c72d8109d5d5eae56d4	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0pc0-0443900000-6d03811231513840bd6b	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0001900000-852d3949fa0da999fbb4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0007900000-7eea489d1d7efa89ad83	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1209400000-32cc970b446d3852e318	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-7e444665cccf50f6f849	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001s-0003900000-1b58b94657c3cc05dac8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-8008900000-3cc12b0a94eafaef10e5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uyi-1003900000-5c888251913ae8a80b47	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-4298800000-c11d607bba9f2dc3c53b	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9542000000-bd6635a22cb471b48c15	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-a004816f1a3eaa6588ef	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0001900000-21ca99c0ac4af23573b3	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-2023900000-84c3d77a80ad34457a20	2021-09-07	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Bile Acid Biosynthesis
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.1 uM	Infant (0-1 year old)	Not Specified	Normal	12646728	details
Blood	Detected and Quantified	0 uM	Children (1 - 13 years old)	Both	Normal	2427795	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.76 uM	Children (1-13 years old)	Both	Infantile Refsum disease	2427795	details
Blood	Detected and Quantified	0 uM	Newborn (0-30 days old)	Not Specified	Neonatal adrenoleukodystrophy	9818927	details
Blood	Detected and Quantified	0.013 uM	Newborn (0-30 days old)	Female	Rhizomelic chondrodysplasia punctata	9818927	details
Blood	Detected and Quantified	0.078 uM	Infant (0-1 year old)	Male	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	1.15 uM	Newborn (0-30 days old)	Not Specified	Zellweger syndrome	9818927	details
Blood	Detected and Quantified	0-3.812 uM	Children (1-13 years old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	0.0290-1.0400 uM	Newborn (0-30 days old)	Female	Peroxisomal biogenesis disorder	9818927	details
Blood	Detected and Quantified	0.719 - 0.828 uM	Children (1 - 13 years old)	Male	Classicle Refsum's disease	2427795	details
Blood	Detected and Quantified	13.4 uM	Infant (0-1 year old)	Not Specified	D-Bifunctional Protein Deficiency	12646728	details

Associated Disorders and Diseases

Disease References

Infantile Refsum's disease
Poll-The BT, Saudubray JM, Ogier H, Schutgens RB, Wanders RJ, Schrakamp G, van den Bosch H, Trijbels JM, Poulos A, Moser HW, et al.: Infantile Refsum's disease: biochemical findings suggesting multiple peroxisomal dysfunction. J Inherit Metab Dis. 1986;9(2):169-74. [PubMed:2427795 ]
Rhizomelic chondrodysplasia punctata
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Peroxisomal biogenesis defect
Baumgartner MR, Poll-The BT, Verhoeven NM, Jakobs C, Espeel M, Roels F, Rabier D, Levade T, Rolland MO, Martinez M, Wanders RJ, Saudubray JM: Clinical approach to inherited peroxisomal disorders: a series of 27 patients. Ann Neurol. 1998 Nov;44(5):720-30. [PubMed:9818927 ]
Refsum's disease
Poll-The BT, Saudubray JM, Ogier H, Schutgens RB, Wanders RJ, Schrakamp G, van den Bosch H, Trijbels JM, Poulos A, Moser HW, et al.: Infantile Refsum's disease: biochemical findings suggesting multiple peroxisomal dysfunction. J Inherit Metab Dis. 1986;9(2):169-74. [PubMed:2427795 ]
D-Bifunctional protein deficiency
Rizzo C, Boenzi S, Wanders RJ, Duran M, Caruso U, Dionisi-Vici C: Characteristic acylcarnitine profiles in inherited defects of peroxisome biogenesis: a novel tool for screening diagnosis using tandem mass spectrometry. Pediatr Res. 2003 Jun;53(6):1013-8. doi: 10.1203/01.PDR.0000064902.59052.0F. Epub 2003 Mar 19. [PubMed:12646728 ]

Associated OMIM IDs

266510 (Infantile Refsum's disease)
215100 (Rhizomelic chondrodysplasia punctata)
214100 (Peroxisomal biogenesis defect)
266500 (Refsum's disease)
261515 (D-Bifunctional protein deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022137

KNApSAcK ID

Not Available

Chemspider ID

109066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5577

PubChem Compound

122312

PDB ID

Not Available

ChEBI ID

18402

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029864

References

Synthesis Reference

Batta A K; Mirchandani R; Salen G; Shefer S Synthesis of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid from 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid: configuration in the bile of Alligator mississippiensis. Steroids (1992), 57(4), 162-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mihalik SJ, Steinberg SJ, Pei Z, Park J, Kim DG, Heinzer AK, Dacremont G, Wanders RJ, Cuebas DA, Smith KD, Watkins PA: Participation of two members of the very long-chain acyl-CoA synthetase family in bile acid synthesis and recycling. J Biol Chem. 2002 Jul 5;277(27):24771-9. Epub 2002 Apr 29. [PubMed:11980911 ]
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 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Sterol 26-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:: CYP27A1
Uniprot ID:: Q02318
Molecular weight:: 60234.28

Reactions

5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADPH + Oxygen → Coprocholic acid + NADP + Water	details
3a,7a,12a-Trihydroxy-5b-cholestan-26-al + NADPH + Oxygen + Hydrogen Ion → Coprocholic acid + NADP + Water	details

Enzyme Details

2. Bile acyl-CoA synthetase

General function:: Involved in catalytic activity
Specific function:: Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:: SLC27A5
Uniprot ID:: Q9Y2P5
Molecular weight:: 75384.375

Reactions

Adenosine triphosphate + Coprocholic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoyl-CoA	details
Adenosine triphosphate + Coprocholic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + 3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA	details
Coprocholic acid + Adenosine triphosphate + Coenzyme A → (25R)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoA + Adenosine monophosphate + Pyrophosphate	details

Enzyme Details

3. 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

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Coprocholic acid (HMDB0000601)

MOL for HMDB0000601 (Coprocholic acid)

3D MOL for HMDB0000601 (Coprocholic acid)

3D SDF for HMDB0000601 (Coprocholic acid)

3D-SDF for HMDB0000601 (Coprocholic acid)

PDB for HMDB0000601 (Coprocholic acid)

3D PDB for HMDB0000601 (Coprocholic acid)

SMILES for HMDB0000601 (Coprocholic acid)

INCHI for HMDB0000601 (Coprocholic acid)

Structure for HMDB0000601 (Coprocholic acid)

3D Structure for HMDB0000601 (Coprocholic acid)

GC-MS

LC-MS/MS

Enzymes

Reactions

Reactions

References

Transporters

References

References