ContaminantDB: 4a-Methyl-5a-cholesta-8,24-dien-3-one

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:25:15 UTC

Update Date

2016-11-09 01:21:14 UTC

Accession Number

CHEM035016

Identification

Common Name

4a-Methyl-5a-cholesta-8,24-dien-3-one

Class

Small Molecule

Description

4a-Methyl-5a-cholesta-8,24-dien-3-one is an intermediate in the Cholesterol biosynthesis pathway, in a reaction catalyzed by the enzyme 3-keto-steroid reductase [EC 1.1.1.270]. (MetaCyc Pathway: cholesterol biosynthesis).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-one	ChEBI
3-Keto-4alpha-methyl-zymosterol	ChEBI
3-Keto-4alpha-methylzymosterol	ChEBI
(4a,5a)-4-Methylcholesta-8,24-dien-3-one	Generator
(4Α,5α)-4-methylcholesta-8,24-dien-3-one	Generator
3-Keto-4a-methyl-zymosterol	Generator
3-Keto-4α-methyl-zymosterol	Generator
3-Keto-4a-methylzymosterol	Generator
3-Keto-4α-methylzymosterol	Generator
4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one	HMDB
4alpha-Methyl-(5alpha)-cholesta-8,24-dien-3-one	ChEBI
4a-Methyl-(5a)-cholesta-8,24-dien-3-one	Generator
4Α-methyl-(5α)-cholesta-8,24-dien-3-one	Generator

Chemical Formula

C₂₈H₄₄O

Average Molecular Mass

396.648 g/mol

Monoisotopic Mass

396.339 g/mol

CAS Registry Number

7377-73-3

IUPAC Name

(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

Traditional Name

(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,27-,28+/m1/s1

InChI Key

DBPZYKHQDWKORQ-SINUOACOSA-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-5-alpha-steroid
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010237 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00056 g/L	ALOGPS
logP	7.22	ALOGPS
logP	7.41	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	124.75 m³·mol⁻¹	ChemAxon
Polarizability	50.94 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02au-1019000000-74f38f1f24d48a20f4b0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-1225e33fc8dbc85e29fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0174-2009000000-71b5c36c965fb209ee16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-2119000000-e1899d14bd1d0142d0f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-133fa32ff7ba267c45fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-61f0749dd8a63d07401e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02di-3009000000-3b2e5d918411006b6e76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0009000000-dabf3142c40a4512bbdc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-5589000000-dc34720a786d693f5d5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8942000000-801d53df4f599d0ae81b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-2f6aa9af0bd8878fb6c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-2f6aa9af0bd8878fb6c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0009000000-ec12d6f6902d6552044d	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000981

FooDB ID

FDB022350

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5918

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

20059529

ChEBI ID

136486

PubChem Compound ID

22298939

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Barton, Derek H. R.; Harrison, David Miles; Moss, G. P.; Widdowson, David A. Biosynthesis of steroids and terpenoids. II. Role of 24-methylene derivatives in the biosynthesis of steroids and terpenoids. Journal of the Chemical Society [Section] C: Organic (1970), (6), 775-85.

4a-Methyl-5a-cholesta-8,24-dien-3-one (CHEM035016)

Structure for CHEM035016: 4a-Methyl-5a-cholesta-8,24-dien-3-one