Showing Compound 5alpha-Cholestanone (FDB022292)

Record Information

Version

1.0

Creation date

2011-09-21 00:11:38 UTC

Update date

2015-10-09 22:29:21 UTC

Primary ID

FDB022292

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5alpha-Cholestanone

Description

5alpha-Cholestanone, also known as coprostanone or 5α-cholestanone, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanone is considered to be a sterol. Based on a literature review a significant number of articles have been published on 5alpha-Cholestanone.

CAS Number

566-88-1

Structure

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

Synonyms

Synonym	Source
5a-Cholestanone	Generator
5Α-cholestanone	Generator
(5a,17b)-17-Octylandrostan-3-one	HMDB
(5alpha)-Cholestan-3-one	HMDB
(5alpha)-Cholestanone	HMDB
5a(H)-Cholestan-3-one	HMDB
5a-Cholestan-3-one	HMDB
5alpha-Cholestane-3-one	HMDB
5alpha-Coprostanone	HMDB
Coprostanone, (5alpha)-isomer	HMDB
Coprostanone, (5beta)-isomer	HMDB
Coprostanone	HMDB
5-alpha-Cholestan-3-one	HMDB
5alpha-Cholestan-3-one	ChEBI
5alpha-Cholestanone	hmdb
5α-cholestan-3-one	Generator

Predicted Properties

Property	Value	Source
Water Solubility	1.4e-05 g/L	ALOGPS
logP	6.65	ALOGPS
logP	7.73	ChemAxon
logS	-7.4	ALOGPS
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	5	ChemAxon
Refractivity	118.74 m³·mol⁻¹	ChemAxon
Polarizability	50.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C27H46O

IUPAC name

(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

InChI Identifier

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

PESKGJQREUXSRR-UXIWKSIVSA-N

Isomeric SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

Average Molecular Weight

386.6535

Monoisotopic Molecular Weight

386.354866094

Classification

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

3-oxo steroid (CHEBI:17762 )
Cholesterol and derivatives (LMST01010174 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolic syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Biofluid and excreta:

Urine

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Multicellular process:

Inflammatory response

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	5alpha-Cholestanone, non-derivatized, GC-MS Spectrum	splash10-054o-3920000000-1e285528ee9f0b57935d	Spectrum
GC-MS	5alpha-Cholestanone, non-derivatized, GC-MS Spectrum	splash10-054o-3920000000-6bb813789665ec6a1628	Spectrum
GC-MS	5alpha-Cholestanone, non-derivatized, GC-MS Spectrum	splash10-054o-3920000000-1e285528ee9f0b57935d	Spectrum
GC-MS	5alpha-Cholestanone, non-derivatized, GC-MS Spectrum	splash10-054o-3920000000-6bb813789665ec6a1628	Spectrum
Predicted GC-MS	5alpha-Cholestanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-1119000000-9809fd6827c971c15cbd	Spectrum
Predicted GC-MS	5alpha-Cholestanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0009000000-4d86603e7a3a04181d6b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9700000000-ab5536500bf3ce457af0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05nf-9400000000-df0bf747717b6f902997	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-d67fc5e4a90e5d444b4c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avr-3109000000-6cb93905134a4bd15b66	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-4129000000-9147166fdcb0a41b5fb9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-dc54e67e8b668159df03	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-e72d372e493f1796a572	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-2019000000-49f63f8ed5d9e7e3d673	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-0799374e96775b3163db	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-85d8a5bf63fedb0c361c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06dj-9164000000-a2efdb351bfe2dea81fd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9710000000-de7ec5cb56f34f7b69c5	2021-09-23	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum