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Record Information
Version1.0
Creation Date2016-09-30 22:29:15 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0000359
Secondary Accession Numbers
  • BMDB00359
Metabolite Identification
Common Name3a,7a-Dihydroxycoprostanic acid
Description3alpha,7alpha-Dihydroxycoprostanic acid, also known as 3alpha,7alpha-dihydroxy-5beta-cholestanate or 3α,7α-dihydroxy-5β-cholestanate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 3alpha,7alpha-Dihydroxycoprostanic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholestanateChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanic acidChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoateChEBI
3alpha,7alpha-Dihydroxy-5beta-cholestanoic acidChEBI
3a,7a-Dihydroxy-5b-cholestanateGenerator
3a,7a-Dihydroxy-5b-cholestanic acidGenerator
3Α,7α-dihydroxy-5β-cholestanateGenerator
3Α,7α-dihydroxy-5β-cholestanic acidGenerator
3a,7a-Dihydroxy-5b-cholestanoateGenerator
3a,7a-Dihydroxy-5b-cholestanoic acidGenerator
3Α,7α-dihydroxy-5β-cholestanoateGenerator
3Α,7α-dihydroxy-5β-cholestanoic acidGenerator
3a,7a-DihydroxycoprostanateGenerator
3a,7a-Dihydroxycoprostanic acidGenerator
3alpha,7alpha-DihydroxycoprostanateGenerator
3Α,7α-dihydroxycoprostanateGenerator
3Α,7α-dihydroxycoprostanic acidGenerator
3a,7a-Dihydroxy-5b-cholestan-26-OateHMDB
3a,7a-Dihydroxy-5b-cholestan-26-Oic acidHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-OateHMDB
3Α,7α-dihydroxy-5β-cholestan-26-OateHMDB
3Α,7α-dihydroxy-5β-cholestan-26-Oic acidHMDB
(3Α,5β,7α)-3,7-dihydroxycholestan-26-Oic acidHMDB
(3a,5b,7a)-3,7-Dihydroxycholestan-26-Oic acidHMDB
(3alpha,5beta,7alpha)-3,7-Dihydroxycholestan-26-Oic acidHMDB
3Α,7α-hydroxy-5β-cholestan-26-Oic acidHMDB
3a,7a-Hydroxy-5β-cholestan-26-Oic acidHMDB
3alpha,7alpha-Hydroxy-5β-cholestan-26-Oic acidHMDB
3a,7a-Hydroxy-5b-cholestan-26-OateHMDB
3a,7a-Hydroxy-5b-cholestan-26-Oic acidHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oic acidHMDB
3alpha,7alpha-Dihydroxycoprostanic acidHMDB
Chemical FormulaC27H46O4
Average Molecular Weight434.661
Monoisotopic Molecular Weight434.339609961
IUPAC Name(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid
CAS Registry Number17974-66-2
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])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeyITZYGDKGRKKBSN-HKFUITGCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
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
logP4.02ALOGPS
logP5.15ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.05 m³·mol⁻¹ChemAxon
Polarizability52.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-0007900000-55bf6ba08fdb23cc5f37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0009200000-3864d6012d9e0f3baf02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06di-1019000000-1d984e3a244a1acc4fd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-8b656f3d458df7baa276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00sr-0007900000-8c41fc1f2328cf805012View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-6009200000-226e124be38dd986fd54View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000359
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021979
KNApSAcK IDNot Available
Chemspider ID4447327
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5348
PubChem Compound5284239
PDB IDNot Available
ChEBI ID16577
References
Synthesis ReferenceHanson, Russell Floyd. Isolation, identification, formation, and metabolism of 3a, 7a-hydroxy-5b-cholestan-26-oic acid in man. (1972), 73 pp. CAN 78:27152 AN 1973:27152
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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-Dihydroxy-5b-cholestan-26-al → 3a,7a-Dihydroxycoprostanic aciddetails
General function:
Not Available
Specific function:
Mediates the ATP-dependent import of long-chain fatty acids (LCFA) into the cell by mediating their translocation at the plasma membrane. Has also an acyl-CoA ligase activity for long-chain and very-long-chain fatty acids. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane-associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LCFA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism.
Gene Name:
SLC27A1
Uniprot ID:
Q3ZKN0
Molecular weight:
71123.0
Reactions
3a,7a-Dihydroxycoprostanic acid + Adenosine triphosphate + Coenzyme A → 3a,7a-Dihydroxy-5b-cholestanoyl-CoA + Pyrophosphate + 3'-AMPdetails