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Showing Compound 3a,7a-Dihydroxycoprostanic acid (FDB021979)

Record Information
Version1.0
Creation date2011-09-21 00:06:25 UTC
Update date2015-07-21 06:56:55 UTC
Primary IDFDB021979
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3a,7a-Dihydroxycoprostanic acid
Description3a,7a-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID 864325) 3a,7a-Dihydroxycoprostanic acid is the precursor to chenodeoxycholic acid A bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on 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. [HMDB]
CAS Number17974-66-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3a,7a-DihydroxycoprostanateGenerator
3a,7a-Dihydroxy-5b-cholestan-26-OateHMDB
3a,7a-Dihydroxy-5b-cholestan-26-Oic acidHMDB
3a,7a-Dihydroxy-5b-cholestanoateHMDB
3a,7a-Dihydroxy-5b-cholestanoic acidHMDB
3a,7a-Hydroxy-5b-cholestan-26-OateHMDB
3a,7a-Hydroxy-5b-cholestan-26-Oic acidHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-OateHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oic acidHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanateHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanic acidHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanoateHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanoic acidHMDB
3a,7a-Dihydroxy-5b-cholestan-26-oatehmdb
3a,7a-Dihydroxy-5b-cholestan-26-oic acidhmdb
3a,7a-Dihydroxycoprostanic acidhmdb
3a,7a-Hydroxy-5b-cholestan-26-oatehmdb
3a,7a-Hydroxy-5b-cholestan-26-oic acidhmdb
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oatehmdb
3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acidhmdb
3alpha,7alpha-dihydroxy-5beta-cholestanic acidhmdb
3alpha,7alpha-dihydroxy-5beta-cholestanoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
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
Polarizability52.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H46O4
IUPAC name(6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid
InChI IdentifierInChI=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-KLYSAGIUSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])C3[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
Average Molecular Weight434.6517
Monoisotopic Molecular Weight434.33960996
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3a,7a-Dihydroxycoprostanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-066r-0458900000-e362f9ddb933450731eeSpectrum
Predicted GC-MS3a,7a-Dihydroxycoprostanic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1210159000-481d95d334ecf3f4f9b9Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-0007900000-55bf6ba08fdb23cc5f372017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-0009200000-3864d6012d9e0f3baf022017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06di-1019000000-1d984e3a244a1acc4fd52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-8b656f3d458df7baa2762017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00sr-0007900000-8c41fc1f2328cf8050122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-6009200000-226e124be38dd986fd542017-09-01View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477686
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00359
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference