ChemFOnt: Showing chemical card for ent-16beta-Methoxy-19-kauranoic acid (CFc000017289)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:12 UTC

Chemfont ID

CFc000017289

Molecule Identification

Common Name

ent-16beta-Methoxy-19-kauranoic acid

Definition

ent-16beta-Methoxy-19-kauranoic acid is found in alcoholic beverages. ent-16beta-Methoxy-19-kauranoic acid is a constituent of Annona glabra (pond apple)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
ent-16b-Methoxy-19-kauranoate	Generator
ent-16b-Methoxy-19-kauranoic acid	Generator
ent-16beta-Methoxy-19-kauranoate	Generator
ent-16Β-methoxy-19-kauranoate	Generator
ent-16Β-methoxy-19-kauranoic acid	Generator
14-Methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₁H₃₄O₃

Average Molecular Weight

334.4929

Monoisotopic Molecular Weight

334.250794954

IUPAC Name

14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

38308-35-9

SMILES

COC1(C)CC23CC1CCC2C1(C)CCCC(C)(C1CC3)C(O)=O

InChI Identifier

InChI=1S/C21H34O3/c1-18-9-5-10-19(2,17(22)23)15(18)8-11-21-12-14(6-7-16(18)21)20(3,13-21)24-4/h14-16H,5-13H2,1-4H3,(H,22,23)

InChI Key

VYVVNCBNYVCVGC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Not Available

Substituents

Not Available

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: HMDB0036302)

Source

Endogenous

Endogenous (HMDB: HMDB0036302)

Plant

Plant (HMDB: HMDB0036302)

Animal

Animal (HMDB: HMDB0036302)

Exogenous

Food

Food (HMDB: HMDB0036302)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0036302)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036302)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036302)

Lipid metabolism pathway (HMDB: HMDB0036302)

Cellular process

Cell signaling (HMDB: HMDB0036302)

Biochemical process

Lipid transport (HMDB: HMDB0036302)

Role

Biological role

Energy source (HMDB: HMDB0036302)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036302)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	4.33	ALOGPS
logP	4.48	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	39.09 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

HMDB0036302

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015170

KNApSAcK ID

Not Available

Chemspider ID

433824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

495571

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for ent-16beta-Methoxy-19-kauranoic acid (CFc000017289)

MOL for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

3D MOL for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

3D SDF for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

3D-SDF for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

PDB for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

3D PDB for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

SMILES for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

INCHI for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

Structure for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)

3D Structure for CFc000017289 (ent-16beta-Methoxy-19-kauranoic acid)