ChemFOnt: Showing chemical card for ent-7alpha-hydroxykaur-16-en-19-oate (CFc000283861)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:37:31 UTC

Chemfont ID

CFc000283861

Molecule Identification

Common Name

ent-7alpha-hydroxykaur-16-en-19-oate

Definition

Ent-7alpha-hydroxykaur-16-en-19-oate is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids 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. Ent-7alpha-hydroxykaur-16-en-19-oate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ent-7alpha-hydroxykaur-16-en-19-oate can be found in a number of food items such as greenthread tea, cardamom, agave, and hickory nut, which makes ent-7alpha-hydroxykaur-16-en-19-oate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
ent-7Α-hydroxykaur-16-en-19-Oic acid	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.457

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

Traditional Name

2-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC12CCCC(C)(C1CC(O)C13CC(CCC21)C(=C)C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-12-10-20-11-13(12)5-6-14(20)18(2)7-4-8-19(3,17(22)23)15(18)9-16(20)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)

InChI Key

KMLXVEXJZSTMBV-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

Substituents

Kaurane diterpenoid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
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

Not Available

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Gibberellin A12 Biosynthesis (PathBank: SMP0012068)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	2.94	ALOGPS
logP	3.58	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-0.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.88 m³·mol⁻¹	ChemAxon
Polarizability	36.29 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030845

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

14487041

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for ent-7alpha-hydroxykaur-16-en-19-oate (CFc000283861)

MOL for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D MOL for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D SDF for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D-SDF for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

PDB for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D PDB for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

SMILES for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

INCHI for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

Structure for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)

3D Structure for CFc000283861 (ent-7alpha-hydroxykaur-16-en-19-oate)