ChemFOnt: Showing chemical card for Methyl 15beta-hydroxy-19-trachylobanoate (CFc000336887)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:17 UTC

Chemfont ID

CFc000336887

Molecule Identification

Common Name

Methyl 15beta-hydroxy-19-trachylobanoate

Definition

15beta-hydroxy-19-trachylobanoic acid 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. 15beta-hydroxy-19-trachylobanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 15beta-hydroxy-19-trachylobanoic acid can be found in fats and oils, which makes 15beta-hydroxy-19-trachylobanoic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(ent-15b)-15-Hydroxy-19-trachylobanoate	Generator
(ent-15b)-15-Hydroxy-19-trachylobanoic acid	Generator
(ent-15beta)-15-Hydroxy-19-trachylobanoate	Generator
(ent-15Β)-15-hydroxy-19-trachylobanoate	Generator
(ent-15Β)-15-hydroxy-19-trachylobanoic acid	Generator
16-Hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

Traditional Name

16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid

CAS Registry Number

83508-81-0

SMILES

CC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O

InChI Identifier

InChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23)

InChI Key

MHVNHDYWKUKRRJ-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

Atisane diterpenoid
Kaurane diterpenoid
Villanovane, atisane, trachylobane or helvifulvane diterpenoid
Alkaloid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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: HMDB0036839)

Source

Endogenous

Endogenous (HMDB: HMDB0036839)

Animal

Animal (HMDB: HMDB0036839)

Exogenous

Food

Food (HMDB: HMDB0036839)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036839)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036839)

Lipid metabolism pathway (HMDB: HMDB0036839)

Cellular process

Cell signaling (HMDB: HMDB0036839)

Biochemical process

Lipid transport (HMDB: HMDB0036839)

Role

Biological role

Energy source (HMDB: HMDB0036839)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036839)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.33	ALOGPS
logP	3.31	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-0.4	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	86.97 m³·mol⁻¹	ChemAxon
Polarizability	36.16 Å³	ChemAxon
Number of Rings	5	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

HMDB0036839

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021672

KNApSAcK ID

Not Available

Chemspider ID

35014269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752061

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Methyl 15beta-hydroxy-19-trachylobanoate (CFc000336887)

MOL for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D MOL for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D SDF for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D-SDF for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

PDB for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D PDB for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

SMILES for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

INCHI for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

Structure for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)

3D Structure for CFc000336887 (Methyl 15beta-hydroxy-19-trachylobanoate)