Showing Compound fecosterol (FDB030856)

Record Information

Version

1.0

Creation date

2015-05-07 20:18:37 UTC

Update date

2019-11-26 03:21:55 UTC

Primary ID

FDB030856

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

fecosterol

Description

Fecosterol, also known as 24-methylene-5alpha-cholest-8-en-3beta-ol or delta-8(24),28-ergostadienol, belongs to ergosterols and derivatives class of compounds. Those are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, fecosterol is considered to be a sterol lipid molecule. Fecosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Fecosterol can be synthesized from 5alpha-ergostane. Fecosterol can also be synthesized into fecosterol ester. Fecosterol can be found in a number of food items such as jew's ear, lima bean, persimmon, and european plum, which makes fecosterol a potential biomarker for the consumption of these food products. Fecosterol may be a unique S.cerevisiae (yeast) metabolite. Fecosterol is a sterol made by certain fungi and lichens .

CAS Number

516-86-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3beta)-Isomer OF fecosterol	MeSH
24-Methylene-5a-cholest-8-en-3b-ol	Generator
24-Methylene-5alpha-cholest-8-en-3beta-ol	ChEBI
24-Methylene-5α-cholest-8-en-3β-ol	Generator
24-Methylene-cholest-8-en-3b-ol	Generator
24-Methylene-cholest-8-en-3beta-ol	ChEBI
24-Methylene-cholest-8-en-3β-ol	Generator
delta-8(24),28-Ergostadienol	ChEBI
Δ-8(24),28-ergostadienol	Generator

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00083 g/L	ALOGPS
logP	6.65	ALOGPS
logP	7.01	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	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	124.68 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

C28H46O

IUPAC name

(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

InChI Identifier

InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18,20-22,24-25,29H,3,7-17H2,1-2,4-6H3/t20-,21+,22+,24-,25+,27+,28-/m1/s1

InChI Key

SLQKYSPHBZMASJ-QKPORZECSA-N

Isomeric SMILES

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

Average Molecular Weight

398.6642

Monoisotopic Molecular Weight

398.354866094

Classification

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
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-sterol (CHEBI:17038 )
Cholesterol and derivatives (C04525 )
Ergosterols and C24-methyl derivatives (C04525 )
Ergosterols and C24-methyl derivatives (LMST01030095 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
Predicted GC-MS	fecosterol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001j-0019000000-4a337e3ab572869d5978	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-6059000000-66cb566725fe3979de6f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-6194000000-e66d0b9546e54d7c12b9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-d618dab195514d0c7bd6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-023dcac6f0c7eab01b94	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2019000000-e6765e76cb50aa2e41b9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-0ca06bc1a59e9690d939	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-0ca06bc1a59e9690d939	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0019000000-c291f31f16695acf3118	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0039000000-64f7710a14da25c485d9	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-8259000000-d9f24f47df06d778f58a	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9640000000-dc358966f446c6d8e5a7	2021-10-21	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound fecosterol (FDB030856)

Structure for FDB030856 (fecosterol)