ChemFOnt: Showing chemical card for (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid (CFc000017697)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:49 UTC

Chemfont ID

CFc000017697

Molecule Identification

Common Name

(ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid

Definition

(ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid is found in coffee and coffee products. (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid is a constituent of roasted coffee.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Bis(4-methoxyphenyl)-1,3-butanediol, 9ci	HMDB
14-Hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylate	Generator
(ent-16BetaOH)-16,17-dihydroxy-9(11)-kauren-19-Oate	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylic acid

Traditional Name

14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-10-ene-5-carboxylic acid

CAS Registry Number

55483-24-4

SMILES

CC1(CCCC2(C)C1CCC13CC(CC=C21)C(O)(CO)C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h5,13-14,21,24H,3-4,6-12H2,1-2H3,(H,22,23)

InChI Key

QSJIZGQGHYROGD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Phenylpropane
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036760)

Source

Endogenous

Endogenous (HMDB: HMDB0036760)

Plant

Coffea (HMDB: HMDB0036760)

Animal

Animal (HMDB: HMDB0036760)

Exogenous

Food

Food (HMDB: HMDB0036760)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0036760)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036760)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036760)

Lipid metabolism pathway (HMDB: HMDB0036760)

Cellular process

Cell signaling (HMDB: HMDB0036760)

Biochemical process

Lipid transport (HMDB: HMDB0036760)

Role

Biological role

Energy source (HMDB: HMDB0036760)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036760)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.19	ALOGPS
logP	2.39	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.66 m³·mol⁻¹	ChemAxon
Polarizability	37.16 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

HMDB0036472

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015422

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

73819207

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid (CFc000017697)

MOL for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

3D MOL for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

3D SDF for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

3D-SDF for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

PDB for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

3D PDB for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

SMILES for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

INCHI for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

Structure for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)

3D Structure for CFc000017697 ((ent-16betaOH)-16,17-Dihydroxy-9(11)-kauren-19-oic acid)