ChemFOnt: Showing chemical card for (+)-Hardwickiic acid (CFc000282431)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:47 UTC

Chemfont ID

CFc000282431

Molecule Identification

Common Name

(+)-Hardwickiic acid

Definition

(+)-hardwickiic acid is a member of the class of compounds known as colensane and clerodane diterpenoids. Colensane and clerodane diterpenoids are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations (+)-hardwickiic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (+)-hardwickiic acid can be found in blackcurrant, which makes (+)-hardwickiic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-[2-(Furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator
(+)-Hardwickiate	Generator
Hardwickic acid, (-)-isomer	MeSH
Hardwickic acid	MeSH

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

None

SMILES

CC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)

InChI Key

HHWOKJDCJVESIF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302915)

Food

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0071 g/L	ALOGPS
logP	5.33	ALOGPS
logP	5.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.08 m³·mol⁻¹	ChemAxon
Polarizability	36.26 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302915

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006884

KNApSAcK ID

Not Available

Chemspider ID

26503523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559627

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (+)-Hardwickiic acid (CFc000282431)

MOL for CFc000282431 ((+)-Hardwickiic acid)

3D MOL for CFc000282431 ((+)-Hardwickiic acid)

3D SDF for CFc000282431 ((+)-Hardwickiic acid)

3D-SDF for CFc000282431 ((+)-Hardwickiic acid)

PDB for CFc000282431 ((+)-Hardwickiic acid)

3D PDB for CFc000282431 ((+)-Hardwickiic acid)

SMILES for CFc000282431 ((+)-Hardwickiic acid)

INCHI for CFc000282431 ((+)-Hardwickiic acid)

Structure for CFc000282431 ((+)-Hardwickiic acid)

3D Structure for CFc000282431 ((+)-Hardwickiic acid)