ChemFOnt: Showing chemical card for 7a,12a-Dihydroxy-cholestene-3-one (CFc000001480)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:07 UTC

Chemfont ID

CFc000001480

Molecule Identification

Common Name

7a,12a-Dihydroxy-cholestene-3-one

Definition

7a,12a-Dihydroxy-cholestene-3-one is an intermediate in bile acid synthesis; is considerably higher in patients with cerebrotendinous xanthomatosis (CTX) than in the normal liver. (PMID 7017048 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-a,12-a-Dihydroxy-4-cholesten-3-one	HMDB
7-a,12-a-Dihydroxycholest-4-en-3-one	HMDB
7-a,12-alpha-Dihydroxy-4-cholesten-3-one	HMDB
7-a,12-alpha-Dihydroxycholest-4-en-3-one	HMDB
7-alpha,12-alpha-Dihydroxy-4-cholesten-3-one	HMDB
7-alpha,12-alpha-Dihydroxycholest-4-en-3-one	HMDB
7alpha,12alpha-Dihydroxy-cholestene-3-one	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

Traditional Name

(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one

CAS Registry Number

None

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

VJGNBLOGSXHTLR-JFXJTJEYSA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-oxo-delta-1-steroid
3-oxosteroid
7-hydroxysteroid
Oxosteroid
12-hydroxysteroid
Hydroxysteroid
Delta-1-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0002197)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0002197)

Tissue

All Tissues (HMDB: HMDB0002197)

Connective tissue

Adipose tissue (HMDB: HMDB0002197)

Nervous tissue

Hepatic tissue (HMDB: HMDB0002197)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002197)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002197)

Source

Endogenous

Endogenous (HMDB: HMDB0002197)

Animal

Animal (HMDB: HMDB0002197)

Exogenous

Food

Food (HMDB: HMDB0002197)

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: HMDB0002197)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002197)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0002197)
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: HMDB0002197)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0002197)

Cellular process

Cell signaling (HMDB: HMDB0002197)

Biochemical process

Lipid transport (HMDB: HMDB0002197)

Multicellular process

Inflammatory response (HMDB: HMDB0002197)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002197)

Molecular messenger

Hormone (HMDB: HMDB0002197)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002197)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	4.69	ALOGPS
logP	5.18	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.94 m³·mol⁻¹	ChemAxon
Polarizability	50.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon