ChemFOnt: Showing chemical card for 7-a,27-Dihydroxycholesterol (CFc000002701)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:39 UTC

Chemfont ID

CFc000002701

Molecule Identification

Common Name

7-a,27-Dihydroxycholesterol

Definition

7-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Cholestene-3beta,7alpha,26-triol	ChEBI
7-alpha,27-Dihydroxycholesterol	ChEBI
Cholest-5-ene-3beta,7alpha,26-triol	ChEBI
Cholest-5-ene-3beta,7alpha,27-triol	ChEBI
5-Cholestene-3b,7a,26-triol	Generator
5-Cholestene-3β,7α,26-triol	Generator
7-Α,27-dihydroxycholesterol	Generator
Cholest-5-ene-3b,7a,26-triol	Generator
Cholest-5-ene-3β,7α,26-triol	Generator
Cholest-5-ene-3b,7a,27-triol	Generator
Cholest-5-ene-3β,7α,27-triol	Generator
Cholest-5-ene-3,7,27-triol	MeSH
7alpha,26-Dihydroxycholesterol	HMDB
7alpha,27-Dihydroxycholesterol	HMDB
Cholest-5-ene-3- b,7-a,27-triol	HMDB
Cholest-5-ene-3-b,7-a,27-triol	HMDB
Cholest-5-ene-3-beta,7-alpha,27-triol	HMDB

Chemical Formula

C₂₇H₄₆O₃

Average Molecular Weight

418.6523

Monoisotopic Molecular Weight

418.344695338

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 Name

7α,27-dihydroxycholesterol

CAS Registry Number

4725-24-0

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 Key

RXMHNAKZMGJANZ-DTTSCKGMSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Trihydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Primary alcohol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triol (CHEBI:18431 )
7alpha-hydroxy steroid (CHEBI:18431 )
26-hydroxy steroid (CHEBI:18431 )
oxysterol (CHEBI:18431 )
Cholesterol and derivatives (C06341 )
C27 bile acids, alcohols, and derivatives (LMST04030081 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006281)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006281)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006281)

Source

Endogenous

Endogenous (HMDB: HMDB0006281)

Animal

Animal (HMDB: HMDB0006281)

Exogenous

Food

Food (HMDB: HMDB0006281)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006281)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006281)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0006281)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006281)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0006281)

Cellular process

Cell signaling (HMDB: HMDB0006281)

Biochemical process

Lipid transport (HMDB: HMDB0006281)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006281)

Molecular messenger

Hormone (HMDB: HMDB0006281)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006281)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0051 g/L	ALOGPS
logP	4.67	ALOGPS
logP	4.6	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.91 m³·mol⁻¹	ChemAxon
Polarizability	52.19 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon