Showing Compound Cholestanol (FDB012122)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:00 UTC

Update date

2019-11-26 03:06:14 UTC

Primary ID

FDB012122

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cholestanol

Description

5alpha-Cholestanol, also known as cholestanol or dihydrocholesterol, 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-cholestanol is considered to be a sterol. Based on a literature review a significant number of articles have been published on 5alpha-Cholestanol.

CAS Number

80-97-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3beta,5alpha)-Cholestan-3-ol	ChEBI
Cholestanol	ChEBI
Dihydrocholesterol	ChEBI
Zymostanol	ChEBI
(3b,5a)-Cholestan-3-ol	Generator
(3Β,5α)-cholestan-3-ol	Generator
5a-Cholestanol	Generator
5Α-cholestanol	Generator
5 alpha Cholestan 3 beta ol	HMDB
5 beta Cholestan 3 beta ol	HMDB
5 beta-Cholestan-3 beta-ol	HMDB
beta Cholestanol	HMDB
beta-Ol, 5 beta-cholestan-3	HMDB
5 alpha Cholestan 3 alpha ol	HMDB
5 alpha-Cholestan-3 beta-ol	HMDB
Cholestan 3 ol	HMDB
Cholestanol, (3alpha, 5beta)-isomer	HMDB
Coprosterol	HMDB
beta-Cholestanol	HMDB
5 beta-Cholestan-3 alpha-ol	HMDB
Coprostanol	HMDB
5 alpha-Cholestan-3 alpha-ol	HMDB
Cholestan-3-ol	HMDB
beta-Cholestan-3 beta-ol, 5	HMDB
3b-Hydroxy-5a-cholestane	HMDB
3b-Hydroxycholestane	HMDB
5a-Cholestan-3b-ol	HMDB
5a-Dihydrocholesterol	HMDB
Cholestan-3b-ol	HMDB
Dihydrocholesterin	HMDB
Epicholestanol	HMDB
5alpha-Cholestanol	ChEBI
β-Cholestanol	biospider
3-β-Cholestanol	biospider
3-beta-Cholestanol	biospider
3-beta-Hydroxycholestane	biospider
3β-Hydroxy-5α-cholestane	biospider
3β-Hydroxycholestane	biospider
3beta-Cholestanol	biospider
3beta-Hydroxy-5beta-cholestanol	biospider
5α-Cholestan-3β-ol	biospider
5α-Cholestanol	biospider
Cholestan-3β-ol	biospider
Dihydrolathosterol	manual
Lathostanol	manual

Predicted Properties

Property	Value	Source
Water Solubility	1.5e-05 g/L	ALOGPS
logP	7.02	ALOGPS
logP	7.52	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.77 m³·mol⁻¹	ChemAxon
Polarizability	51.27 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

C27H48O

IUPAC name

(1S,2S,5S,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-ol

InChI Identifier

InChI=1S/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

QYIXCDOBOSTCEI-QCYZZNICSA-N

Isomeric SMILES

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

Average Molecular Weight

388.6694

Monoisotopic Molecular Weight

388.370516158

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
Cholesterol
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:86570 )
cholestanoid (CHEBI:86570 )
Cholesterol and derivatives (LMST01010077 )

Ontology

Ingestion

Tissue and substructures:

Organ and components:

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

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 - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 83.44%; H 12.45%; O 4.12%	DFC
Melting Point	Mp 142-143°	DFC
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	[a]22D +27.4 (CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Cholestanol, 1 TMS, GC-MS Spectrum	splash10-0a7l-8910000000-cb54fe639b59ac574d48	Spectrum
GC-MS	Cholestanol, non-derivatized, GC-MS Spectrum	splash10-0159-2971000000-c73c47a340a1d4a167e1	Spectrum
GC-MS	Cholestanol, non-derivatized, GC-MS Spectrum	splash10-001c-9685000000-f1bd7d21900c66c26e86	Spectrum
GC-MS	Cholestanol, non-derivatized, GC-MS Spectrum	splash10-0a7l-8910000000-cb54fe639b59ac574d48	Spectrum
GC-MS	Cholestanol, non-derivatized, GC-MS Spectrum	splash10-0a4m-3920000000-deaba49a3e34c5a9a998	Spectrum
Predicted GC-MS	Cholestanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i0-0109000000-761dcf3fe040f44fa80e	Spectrum
Predicted GC-MS	Cholestanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-3104900000-654dcbe9dd07b5a589f2	Spectrum
Predicted GC-MS	Cholestanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cholestanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cholestanol, TBDMS_1_1, 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-1019000000-713d1937c93d1a00cc54	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000j-9002000000-f96eb85165088475ddbc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05o1-9200000000-8819828d6963c4e8290d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	splash10-0159-2971000000-c73c47a340a1d4a167e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-001c-9685000000-f1bd7d21900c66c26e86	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0009000000-57023400d5e478a8c746	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-3039000000-9ce6c0a362b9f376d3f0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-4159000000-32959ebb75235db63ac3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-134a888410f8beddca3b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-c42f43f5e21141f5a909	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-1009000000-8096d56c7bfdd221f9c2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-44afea742dee80d0734e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9032000000-166905331dad000292e6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9820000000-f066461902c4fe39e2d4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-34ef429285e58bb4b314	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-780ac33d63315f658159	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0009000000-2b8e0e9916832dc47876	2021-09-22	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