ChemFOnt: Showing chemical card for 2,3-seco-3-oxoolean-12-en-2-oic acid (CFc000338142)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:32:25 UTC

Chemfont ID

CFc000338142

Molecule Identification

Common Name

2,3-seco-3-oxoolean-12-en-2-oic acid

Definition

2,3-seco-3-Oxoolean-12-en-2-oic acid is a triterpenoid found in gentian root, a bitter food additive and medicinal herb from the herbaceous perennial plant Gentiana lutea (PMID: 12520135 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3-Seco-3-oxooleana-12-ene-2-Oate	Generator

Chemical Formula

C₃₀H₄₈O₃

Average Molecular Weight

456.711

Monoisotopic Molecular Weight

456.360345406

IUPAC Name

2-[(1R,2R,4aR,4bS,6aR,10aR,12aR)-1,4a,4b,6a,9,9-hexamethyl-2-(2-methyl-1-oxopropan-2-yl)-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysen-1-yl]acetic acid

Traditional Name

[(1R,2R,4aR,4bS,6aR,10aR,12aR)-1,4a,4b,6a,9,9-hexamethyl-2-(2-methyl-1-oxopropan-2-yl)-3,4,5,6,7,8,10,10a,12,12a-decahydro-2H-chrysen-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(C)(C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@](C)(CC(O)=O)[C@@]([H])(CC[C@@]12C)C(C)(C)C=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)13-14-27(5)15-16-29(7)20(21(27)17-25)9-10-23-28(6,18-24(32)33)22(26(3,4)19-31)11-12-30(23,29)8/h9,19,21-23H,10-18H2,1-8H3,(H,32,33)/t21-,22-,23+,27+,28-,29+,30+/m0/s1

InChI Key

BUXSYCWKLKUTID-CFYIDONUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

20-oxosteroids

Alternative Parents

Substituents

20-oxosteroid
Diterpenoid
16-hydroxysteroid
16-oxosteroid
Hydroxysteroid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Vegetable

Gentiana lutea (FooDB: FOOD00894)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	7.53	ALOGPS
logP	6.81	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	134.65 m³·mol⁻¹	ChemAxon
Polarizability	54.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000018

KNApSAcK ID

Not Available

Chemspider ID

9202040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11026860

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2,3-seco-3-oxoolean-12-en-2-oic acid (CFc000338142)

MOL for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

3D MOL for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

3D SDF for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

3D-SDF for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

PDB for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

3D PDB for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

SMILES for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

INCHI for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

Structure for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)

3D Structure for CFc000338142 (2,3-seco-3-oxoolean-12-en-2-oic acid)