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Record Information
Version3.6
Creation Date2007-05-22 21:09:59 UTC
Update Date2016-02-11 01:07:27 UTC
HMDB IDHMDB06281
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-a,27-Dihydroxycholesterol
Description7-a,27-dihydroxycholesterol is an intermediate in bile acid biosynthesis. The enzyme 27-Hydroxycholesterol 7alpha-monooxygenase [EC:1.14.13.60] catalyzes the production of this metabolite from 27-hydroxycholesterol. This enzyme reaction is irreversible and occurs in the endoplasmic reticulum.
Structure
Thumb
Synonyms
ValueSource
5-Cholestene-3beta,7alpha,26-triolChEBI
7-alpha,27-DihydroxycholesterolChEBI
Cholest-5-ene-3beta,7alpha,26-triolChEBI
Cholest-5-ene-3beta,7alpha,27-triolChEBI
5-Cholestene-3b,7a,26-triolGenerator
5-Cholestene-3β,7α,26-triolGenerator
7a,26-DihydroxycholesterolGenerator
7α,26-dihydroxycholesterolGenerator
7-a,27-DihydroxycholesterolGenerator
7-α,27-dihydroxycholesterolGenerator
Cholest-5-ene-3b,7a,26-triolGenerator
Cholest-5-ene-3β,7α,26-triolGenerator
Cholest-5-ene-3b,7a,27-triolGenerator
Cholest-5-ene-3β,7α,27-triolGenerator
7alpha,27-DihydroxycholesterolHMDB
Cholest-5-ene-3,7,27-triolHMDB
Cholest-5-ene-3- b,7-a,27-triolHMDB
Cholest-5-ene-3-b,7-a,27-triolHMDB
Cholest-5-ene-3-beta,7-alpha,27-triolHMDB
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name7α,27-dihydroxycholesterol
CAS Registry Number4725-24-0
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)CO
InChI Identifier
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h15,17-18,20-25,28-30H,5-14,16H2,1-4H3/t17?,18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyInChIKey=RXMHNAKZMGJANZ-DTTSCKGMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0051 mg/mLALOGPS
logP4.67ALOGPS
logP4.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.91 m3·mol-1ChemAxon
Polarizability52.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023875
KNApSAcK IDNot Available
Chemspider ID389810
KEGG Compound IDC06341
BioCyc IDCPD-7243
BiGG ID48023
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06281
Metagene LinkHMDB06281
METLIN IDNot Available
PubChem Compound440985
PDB IDNot Available
ChEBI ID18431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
7-a,27-Dihydroxycholesterol + NAD → 7 alpha,26-Dihydroxy-4-cholesten-3-one + NADH + Hydrogen Iondetails