Showing metabocard for 3 beta,7 alpha-Dihydroxy-5-cholestenoate (BMDB0012454)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:52 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0012454
Secondary Accession Numbers
  • BMDB12454
Metabolite Identification
Common Name3 beta,7 alpha-Dihydroxy-5-cholestenoate
Description3beta,7alpha-Dihydroxy-5-cholestenoate, also known as 3b,7a-dihydroxy-5-cholesten-26-Oic acid, 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. 3beta,7alpha-Dihydroxy-5-cholestenoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 3beta,7alpha-Dihydroxy-5-cholestenoate is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3beta,7alpha-Dihydroxy-5-cholesten-26-Oic acidKegg
3b,7a-Dihydroxy-5-cholesten-26-OateGenerator
3b,7a-Dihydroxy-5-cholesten-26-Oic acidGenerator
3beta,7alpha-Dihydroxy-5-cholesten-26-OateGenerator
3Β,7α-dihydroxy-5-cholesten-26-OateGenerator
3Β,7α-dihydroxy-5-cholesten-26-Oic acidGenerator
3b,7a-Dihydroxy-5-cholestenoateGenerator
3b,7a-Dihydroxy-5-cholestenoic acidGenerator
3beta,7alpha-Dihydroxy-5-cholestenoic acidGenerator
3Β,7α-dihydroxy-5-cholestenoateGenerator
3Β,7α-dihydroxy-5-cholestenoic acidGenerator
3,7-Dihydroxy-5-cholestenoic acidHMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oic acidHMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.645
Monoisotopic Molecular Weight432.323959897
IUPAC Name(6R)-6-[(1S,2R,5S,9S,10S,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(1S,2R,5S,9S,10S,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-84-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[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/C27H44O4/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/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeyGYJSAWZGYQXRBS-GRJZKGIBSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP3.92ALOGPS
logP4.9ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.75 m³·mol⁻¹ChemAxon
Polarizability52.17 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v4r-0247900000-6844e920e0f45971085cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1110149000-9481ac260199d7f5b542View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0007900000-ba51b1e65739e23c2f83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0009200000-ad2af6637f0b3ce7d674View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2119000000-87d5606a65d11c0d0bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-11d955c76d3b48e69882View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-0007900000-1344438f254eaafa390dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-6009200000-7340abd91104a8c2fb9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ls-1106900000-2985a04589bff796de8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ba-2159100000-99496085551528fe3dceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-7690000000-313265b61c2dcc7ed040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-3cca5453e09966b932edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0002900000-acd26e8db7d05ca4d858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1002900000-97654ceb214ce880e583View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012454
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17335
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3081084
PDB IDNot Available
ChEBI ID81015
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Prostacyclin synthase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q29626
Molecular weight:
56629.0
Reactions
3beta-Hydroxy-5-cholestenoic acid + NADPH + Oxygen → 3 beta,7 alpha-Dihydroxy-5-cholestenoate + NADP + Waterdetails
Enzyme Details
2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B
Uniprot ID:
P14893
Molecular weight:
42220.0
Reactions
3 beta,7 alpha-Dihydroxy-5-cholestenoate + NAD → 7 alpha-Hydroxy-3-oxo-4-cholestenoate + NADHdetails