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Showing metabocard for Coprocholic acid (BMDB0000601)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:25 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0000601
Secondary Accession Numbers
  • BMDB00601
Metabolite Identification
Common NameCoprocholic acid
DescriptionCoprocholic acid, also known as coprocholate, 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. Coprocholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oic acidChEBI
3,7,12-Trihydroxycholestan-26-Oic acidChEBI
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oic acidGenerator
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-OateGenerator
(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oic acidGenerator
3,7,12-Trihydroxycholestan-26-OateGenerator
CoprocholateGenerator
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-OateHMDB
3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-OateHMDB
3a,7a,12a-Trihydroxy-5b-cholestan-26-Oic acidHMDB
3a,7a,12a-TrihydroxycoprostanateHMDB
3a,7a,12a-Trihydroxycoprostanic acidHMDB
5b-Cholestane-3a,7a,12a-triol-26-OateHMDB
5b-Cholestane-3a,7a,12a-triol-26-Oic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5-beta-cholestan-26-Oic acidHMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25R)-isomerHMDB
3,7,12-Trihydroxycholestan-26-Oic acid, (25S)-isomerHMDB
3Α,7α,12α-trihydroxy-5β-cholestan-26-Oic acidHMDB
3Α,7α,12α-trihydroxycoprostanic acidHMDB
5Β-cholestane-3α,7α,12α-triol-26-Oic acidHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oic acidHMDB
3alpha,7alpha,12alpha-Trihydroxycoprostanic acidHMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-Oic acidHMDB
Trihydroxycoprostanic acidHMDB
Trihydroxycoprostanoic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoic acidHMDB
3a,7a,12a-Trihydroxy-5b-cholestanoateHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoateHMDB
3Α,7α,12α-trihydroxy-5β-cholestanoateHMDB
3Α,7α,12α-trihydroxy-5β-cholestanoic acidHMDB
Coprocholic acidHMDB, ChEBI
Chemical FormulaC27H46O5
Average Molecular Weight450.6511
Monoisotopic Molecular Weight450.334524582
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 Number547-98-8
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 KeyCNWPIIOQKZNXBB-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.12ALOGPS
logP3.91ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.57 m³·mol⁻¹ChemAxon
Polarizability53.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0353900000-c3bc744526d90b133841View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1341349000-6c72d8109d5d5eae56d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001900000-852d3949fa0da999fbb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-0007900000-7eea489d1d7efa89ad83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1209400000-32cc970b446d3852e318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-7e444665cccf50f6f849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001s-0003900000-1b58b94657c3cc05dac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-8008900000-3cc12b0a94eafaef10e5View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Gallbladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000601
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022137
KNApSAcK IDNot Available
Chemspider ID109066
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5577
PubChem Compound122312
PDB IDNot Available
ChEBI ID18402
References
Synthesis ReferenceBatta 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 ReferencesNot Available

Enzymes

Enzyme Details
1. Cholesterol side-chain cleavage enzyme, mitochondrial
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
Reactions
3a,7a,12a-Trihydroxy-5b-cholestan-26-al → Coprocholic aciddetails