ContaminantDB: Stigmastanol

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

Record Information

Version

1.0

Creation Date

2016-05-25 21:11:43 UTC

Update Date

2016-11-09 01:17:45 UTC

Accession Number

CHEM023631

Identification

Common Name

Stigmastanol

Class

Small Molecule

Description

A heteropentacyclic compound that is (20alpha)-16,17-didehydro-18-oxayohimban which is substituted at position 16 by a methoxycarbonyl group and at position 19 by a methyl group. It is a metabolite found in several plant species.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate	ChEBI
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid	Generator
(3b)-Stigmastan-3-ol	HMDB
(3beta)-Stigmastan-3-ol	HMDB
(3beta,5alpha)-Stigmastan-3-ol	HMDB
24-alpha-Ethylcholestanol	HMDB
24a-Ethylcholestanol	HMDB
4a-Methyl-5a,14a-lumistan-3b-ol	HMDB
4a-Methylcampestanol	HMDB
5,6-dihydro-b-Sitosterol	HMDB
5,6-dihydro-beta-Sitosterol	HMDB
5a-Stigmastan-3b-ol	HMDB
5alpha-Stigmastan-3beta-ol	HMDB
b-Sitostanol	HMDB
beta-dihydro-Sitosterol	HMDB
beta-Sitostanol	HMDB, MeSH
dihydro-b-Sitosterol	HMDB
dihydro-beta-Sitosterol	HMDB
Dihydrositosterin	HMDB
Dihydrositosterol	HMDB, MeSH
Fucostanol	HMDB
Sitostanol	HMDB, MeSH
Spinastanol	HMDB
Stigmastan-3-ol	HMDB
Stigmastane-3-beta-ol	HMDB
24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol	MeSH, HMDB
Stigmastanol, (3beta,5beta,24S)-isomer	MeSH, HMDB
24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol	MeSH, HMDB
Stigmastanol	MeSH

Chemical Formula

C₂₉H₅₂O

Average Molecular Mass

416.723 g/mol

Monoisotopic Mass

416.402 g/mol

CAS Registry Number

83-45-4

IUPAC Name

(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

Traditional Name

stigmastane-3-β-ol

SMILES

CCC(CCC(C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C)C(C)C

InChI Identifier

InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3

InChI Key

LGJMUZUPVCAVPU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Ajmalicine-skeleton
18-oxayohimban
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

yohimban alkaloid (CHEBI:9479 )
Indole alkaloids (C11682 )

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	1.1e-05 g/L	ALOGPS
logP	7.23	ALOGPS
logP	8.25	ChemAxon
logS	-7.6	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	6	ChemAxon
Refractivity	128.92 m³·mol⁻¹	ChemAxon
Polarizability	54.93 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	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-066u-4942100000-604c3357e69c5eff6d37	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066u-4942100000-604c3357e69c5eff6d37	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-2109200000-a86730d94764ca5efe85	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3103900000-2af97f9cf8a2adff3196	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0019600000-d66897ecdbe2fe845508	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-4149200000-b304e7e4678a4df85f02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-8089100000-404a21c90ecdfcc88b6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0002900000-5b14a67727dfd30debe9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0004900000-af8991b83701d4b9f081	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0012-1009000000-eebc7b9b36cf260dbceb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-b5f23f2410b0642246b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000900000-bb6fb31d418e3fc0bd50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02ta-0004900000-0b0cca9041a827eb2238	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2125900000-88705afd06ff3d3ec277	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9022300000-71d6fc93ae624cc61e6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9610000000-0304da0e562e0b20612f	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

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00025214

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

9479

PubChem Compound ID

72340

Kegg Compound ID

C11682

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17340319

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19403195

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23285803

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=5050366

Stigmastanol (CHEM023631)

Structure for CHEM023631: Stigmastanol