ChemFOnt: Showing chemical card for F-Tigogenin (CFc000333210)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:05 UTC

Chemfont ID

CFc000333210

Molecule Identification

Common Name

F-Tigogenin

Definition

Neotigogenin, also known as (25s)-5alpha-spirostan-3beta-ol or (3beta,5alpha,25s)-spirostan-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, neotigogenin is considered to be a sterol lipid molecule. Neotigogenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Neotigogenin can be found in fenugreek, garden tomato, and garden tomato (variety), which makes neotigogenin a potential biomarker for the consumption of these food products. .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,5alpha,25S)-Spirostan-3-ol	Kegg
(3b,5a,25S)-Spirostan-3-ol	Generator
(3Β,5α,25S)-spirostan-3-ol	Generator
5-Methyl-6-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
e,e,5-Methyl-4-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
4-Farnesyl-5-methylresorcinol	HMDB
4-trans,trans-Farnesyl-5-methylresorcinol	HMDB
(25S)-5alpha-Spirostan-3beta-ol	HMDB
25S-Tigogenin	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

Traditional Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

CAS Registry Number

470-01-9

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2

InChI Identifier

InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI Key

GMBQZIIUCVWOCD-PUHUBZITSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Spirostane skeleton
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Steroid
Ketal
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:80752 )
spirostan (C16819 )
Spirostanols and derivatives (LMST01080019 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030047)

Source

Endogenous

Endogenous (HMDB: HMDB0030047)

Plant

Plant (HMDB: HMDB0030047)

Animal

Animal (HMDB: HMDB0030047)

Exogenous

Food

Food (HMDB: HMDB0030047)

Herb and spice

Herb

Soft-necked garlic (FooDB: FOOD00850)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0030047)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0030047)

Lipid metabolism pathway (HMDB: HMDB0030047)

Cellular process

Cell signaling (HMDB: HMDB0030047)

Biochemical process

Lipid transport (HMDB: HMDB0030047)

Role

Biological role

Energy source (HMDB: HMDB0030047)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030047)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.3e-05 g/L	ALOGPS
logP	4.52	ALOGPS
logP	5.33	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	119.42 m³·mol⁻¹	ChemAxon
Polarizability	50.87 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030047

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9874426

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for F-Tigogenin (CFc000333210)

MOL for CFc000333210 (F-Tigogenin)

3D MOL for CFc000333210 (F-Tigogenin)

3D SDF for CFc000333210 (F-Tigogenin)

3D-SDF for CFc000333210 (F-Tigogenin)

PDB for CFc000333210 (F-Tigogenin)

3D PDB for CFc000333210 (F-Tigogenin)

SMILES for CFc000333210 (F-Tigogenin)

INCHI for CFc000333210 (F-Tigogenin)

Structure for CFc000333210 (F-Tigogenin)

3D Structure for CFc000333210 (F-Tigogenin)