ChemFOnt: Showing chemical card for (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid (CFc000017693)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:48 UTC

Chemfont ID

CFc000017693

Molecule Identification

Common Name

(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid

Definition

(ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid is found in pulses. (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid is isolated from Phaseolus coccineus (scarlet runner bean).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,3-Dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator
(ent-6a,7a,16AlphaH)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6a,7a,16AlphaH)-6,7,17-trihydroxy-19-kauranoic acid	Generator
(ent-6alpha,7alpha,16AlphaH)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6Α,7α,16alphah)-6,7,17-trihydroxy-19-kauranoate	Generator
(ent-6Α,7α,16alphah)-6,7,17-trihydroxy-19-kauranoic acid	Generator

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

2,3-dihydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

56064-72-3

SMILES

CC12CCCC(C)(C1C(O)C(O)C13CC(CO)C(C1)CCC23)C(O)=O

InChI Identifier

InChI=1S/C20H32O5/c1-18-6-3-7-19(2,17(24)25)15(18)14(22)16(23)20-8-11(4-5-13(18)20)12(9-20)10-21/h11-16,21-23H,3-10H2,1-2H3,(H,24,25)

InChI Key

FQXFNQBHZJYODR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036756)

Source

Endogenous

Endogenous (HMDB: HMDB0036756)

Plant

Fabaceae (HMDB: HMDB0036756)

Animal

Animal (HMDB: HMDB0036756)

Exogenous

Food

Food (HMDB: HMDB0036756)

Pulse

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0036756)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036756)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036756)

Lipid metabolism pathway (HMDB: HMDB0036756)

Cellular process

Cell signaling (HMDB: HMDB0036756)

Biochemical process

Lipid transport (HMDB: HMDB0036756)

Role

Biological role

Energy source (HMDB: HMDB0036756)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036756)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.37 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.57	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.24 m³·mol⁻¹	ChemAxon
Polarizability	38.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030920

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002886

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid (CFc000017693)

MOL for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D MOL for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D SDF for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D-SDF for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

PDB for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D PDB for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

SMILES for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

INCHI for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

Structure for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)

3D Structure for CFc000017693 ((ent-6alpha,7alpha,16alphaH)-6,7,17-Trihydroxy-19-kauranoic acid)