Showing metabocard for 3a,7a-Dihydroxy-5b-cholestane (BMDB0006893)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:27:19 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0006893
Secondary Accession Numbers
  • BMDB06893
Metabolite Identification
Common Name3a,7a-Dihydroxy-5b-cholestane
Description3a,7a-Dihydroxy-5b-cholestane, also known as dihydroxycoprostane or 5b-cholestane-3a,7a-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 3a,7a-dihydroxy-5b-cholestane is considered to be a bile acid lipid molecule. 3a,7a-Dihydroxy-5b-cholestane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3a,7a-Dihydroxy-5b-cholestane is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholestaneChEBI
DihydroxycoprostaneChEBI
5beta-Cholestane-3alpha,7alpha-diolKegg
3Α,7α-dihydroxy-5β-cholestaneGenerator
5b-Cholestane-3a,7a-diolGenerator
5Β-cholestane-3α,7α-diolGenerator
3,7-Dihydroxy-5-cholestaneHMDB
3,7-DihydroxycholestaneHMDB
5alpha-Cholestane-3beta,7beta-diolHMDB
Dihydroxycoprostane, (3alpha,5alpha,7alpha)-isomerHMDB
Dihydroxycoprostane, (3beta,5alpha,7alpha)-isomerHMDB
Chemical FormulaC27H48O2
Average Molecular Weight404.6688
Monoisotopic Molecular Weight404.36543078
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9-diol
Traditional Name5β-cholestane-3α,7α-diol
CAS Registry Number3862-26-8
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])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H48O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h17-25,28-29H,6-16H2,1-5H3/t18-,19+,20-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyAPYVEUGLZHAHDJ-TVRYRFOISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP5.88ALOGPS
logP6.21ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.36 m³·mol⁻¹ChemAxon
Polarizability51.59 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, Positivesplash10-06rl-1219000000-6af223a41b0a7a91af2cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-3220590000-375bc120297d486a3b68View 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, Positivesplash10-052r-0009200000-df25d1509241d9f73f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-2129100000-1bfe2b042bf2b32bbabdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-4129000000-cfef80f1eeab9ccd9236View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0003900000-9badc48971b46507f711View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0009800000-a236fdccb8989fe2c557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-1009000000-ac762387fbd63dd8fee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-b8b020b5e69b09c721f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9013100000-34ed7551b67a9fc921bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9430000000-dd74d7aaa66a164f94b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-82ba826e352c471b5c11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0000900000-3db0959145384e45d712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0000900000-60f92d1adbf02fcd18e9View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006893
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024140
KNApSAcK IDNot Available
Chemspider ID2338356
KEGG Compound IDC05452
BioCyc IDNot Available
BiGG ID45841
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080603
PDB IDNot Available
ChEBI ID28047
References
Synthesis ReferenceNot Available
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-Dihydroxy-5b-cholestane + 3 NADPH + 3 Oxygen → 3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane +3 NADP +3 Waterdetails
Enzyme Details
2. Dihydrodiol dehydrogenase 3
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P52898
Molecular weight:
36784.0
Reactions
7a-Hydroxy-5b-cholestan-3-one + NAD → 3a,7a-Dihydroxy-5b-cholestane + NADPdetails