ContaminantDB: 4alpha-Hydroxymethyl-5alpha-cholesta-8-en-3beta-ol

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

Record Information

Version

1.0

Creation Date

2016-05-27 00:21:57 UTC

Update Date

2016-11-09 01:22:18 UTC

Accession Number

CHEM040690

Identification

Common Name

4alpha-Hydroxymethyl-5alpha-cholesta-8-en-3beta-ol

Class

Small Molecule

Description

4Alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic reduction of 4a-formyl-5a-cholesta-8-en-3b-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
4a-Hydroxymethyl-5a-cholesta-8-en-3b-ol	Generator
4Α-hydroxymethyl-5α-cholesta-8-en-3β-ol	Generator

Chemical Formula

C₂₈H₄₈O₂

Average Molecular Mass

416.680 g/mol

Monoisotopic Mass

416.365 g/mol

CAS Registry Number

Not Available

IUPAC Name

(2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol

Traditional Name

(2S,5S,6R,15R)-6-(hydroxymethyl)-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol

SMILES

CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](CO)C1CC3

InChI Identifier

InChI=1S/C28H48O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h18-19,21-24,26,29-30H,6-17H2,1-5H3/t19?,21-,22?,23?,24?,26-,27+,28-/m0/s1

InChI Key

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	0.0018 g/L	ALOGPS
logP	5.83	ALOGPS
logP	6.04	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	126.65 m³·mol⁻¹	ChemAxon
Polarizability	53.12 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2i-1009200000-599e1f63fce58f7c582d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0002-3101290000-95af824cb5650d8827fe	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	splash10-00kb-0009300000-c3e00eae240a56560ee0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-2019100000-04f6393c9197f1400470	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-6349100000-9ef510556f96a8a65604	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0005900000-9ea36fac8500e81f971a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009300000-2fa2273cdf378f769c7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1009000000-52e44ab5433b14f91fe1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-fa56ba175266d5836db1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0004900000-487336b30e2268367094	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-0009000000-0e59dcb4be1197a5e7bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009700000-e02e80c0289cb944cf4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9128300000-75d6cbfa2681a8db240a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9002000000-8bbcbade157221c3f35e	Spectrum