ChemFOnt: Showing chemical card for 19-Trachylobanoic acid (CFc000283301)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:26 UTC

Chemfont ID

CFc000283301

Molecule Identification

Common Name

19-Trachylobanoic acid

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
19-Trachylobanoate	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

IUPAC Name

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

Traditional Name

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

CAS Registry Number

None

SMILES

CC12CC34CC1C2CC3C1(C)CCCC(C)(C1CC4)C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-17-6-4-7-18(2,16(21)22)14(17)5-8-20-10-13-12(9-15(17)20)19(13,3)11-20/h12-15H,4-11H2,1-3H3,(H,21,22)

InChI Key

FLGAFUAMEXILLB-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
Villanovane, atisane, trachylobane or helvifulvane diterpenoid
Atisane diterpenoid
Alkaloid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303785)

Food

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Not Available

Role

Biological role

Anti septic (HMDB: HMDB0303785)
Juvabional (HMDB: HMDB0303785)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0303785)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	3.19	ALOGPS
logP	4.39	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.61 m³·mol⁻¹	ChemAxon
Polarizability	35.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021677

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

14262763

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 19-Trachylobanoic acid (CFc000283301)

MOL for CFc000283301 (19-Trachylobanoic acid)

3D MOL for CFc000283301 (19-Trachylobanoic acid)

3D SDF for CFc000283301 (19-Trachylobanoic acid)

3D-SDF for CFc000283301 (19-Trachylobanoic acid)

PDB for CFc000283301 (19-Trachylobanoic acid)

3D PDB for CFc000283301 (19-Trachylobanoic acid)

SMILES for CFc000283301 (19-Trachylobanoic acid)

INCHI for CFc000283301 (19-Trachylobanoic acid)

Structure for CFc000283301 (19-Trachylobanoic acid)

3D Structure for CFc000283301 (19-Trachylobanoic acid)