Showing metabocard for 3beta-Hydroxy-5-cholestenoic acid (BMDB0109593)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2020-03-26 13:17:01 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0109593
Secondary Accession NumbersNone
Metabolite Identification
Common Name3beta-Hydroxy-5-cholestenoic acid
Description3beta-Hydroxy-5-cholestenoic acid, also known as 3β-hydroxy-5-cholestenoate or 5-cholesten-3-ol-25-carboxylic acid, belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Based on a literature review a significant number of articles have been published on 3beta-Hydroxy-5-cholestenoic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3b-Hydroxy-5-cholestenoateGenerator
3b-Hydroxy-5-cholestenoic acidGenerator
3beta-Hydroxy-5-cholestenoateGenerator
3Β-hydroxy-5-cholestenoateGenerator
3Β-hydroxy-5-cholestenoic acidGenerator
5-Cholesten-3-ol-25-carboxylic acidMeSH
(25R)-3b-Hydroxycholest-5-en-26-OateGenerator, HMDB
(25R)-3b-Hydroxycholest-5-en-26-Oic acidGenerator, HMDB
(25R)-3beta-Hydroxycholest-5-en-26-OateGenerator, HMDB
(25R)-3Β-hydroxycholest-5-en-26-OateGenerator, HMDB
(25R)-3Β-hydroxycholest-5-en-26-Oic acidGenerator, HMDB
(3beta)-3-Hydroxycholest-5-en-26-oic acidHMDB
(3beta,25R)-3-Hydroxycholest-5-en-26-oic acidHMDB
(3β)-3-Hydroxycholest-5-en-26-oic acidHMDB
(3β,25R)-3-Hydroxycholest-5-en-26-oic acidHMDB
3beta-Hydroxy-5-cholestenoic acidHMDB
3beta-Hydroxycholest-5-en-26-oic acidHMDB
3beta-Hydroxycholest-5-en-27-oic acidHMDB
3β-Hydroxycholest-5-en-26-oic acidHMDB
3β-Hydroxycholest-5-en-27-oic acidHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.646
Monoisotopic Molecular Weight416.329045277
IUPAC Name(2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)C(O)=O
InChI Identifier
InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChI KeyWVXOMPRLWLXFAP-KQOPCUSDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxy-delta-5-steroid
  • 3-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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.57ALOGPS
logP6.05ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.31 m³·mol⁻¹ChemAxon
Polarizability51.55 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-9291456af111b57a086aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0007900000-53d9c33626532c025532View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2003900000-44ce8c22a104fa8cb7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1109500000-59889f5826d4841604c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-2169000000-925cc86a36a9e049df54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-7910000000-ffc877d5e91fdf1f8c9dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012453
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111635
KNApSAcK IDNot Available
Chemspider ID25942571
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound40579073
PDB IDNot Available
ChEBI ID86378
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. 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
27-Hydroxycholesterol + 3 NADPH + 3 Oxygen → 3beta-Hydroxy-5-cholestenoic acid +3 NADP +4 Waterdetails