(+)-Hardwickiic acid (CED0018965)

Record Information

Version

1.0

Creation Date

2016-05-25 22:52:06 UTC

Update Date

2026-04-05 10:41:14 UTC

Accession Number

CHEM026227

Identification

Common Name

(+)-Hardwickiic acid

Class

Small Molecule

Description

(+)-Hardwickiic acid belongs to the diterpenoids, a subclass of prenol lipids within the organic compounds. It is a lipid and lipid-like molecule with the formula C20H28O3 and an average molecular weight of 316.43 g/mol.

Contaminant Type

Insecticide

Chemical 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 Mass

316.435 g/mol

Monoisotopic Mass

316.204 g/mol

CAS Registry Number

1782-65-6

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

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0097000000-fed39af9417d4a080f43	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00rj-0391000000-5e076b8451e26c71ba14	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-2980000000-7f9587534f8731d22563	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0049000000-26269078d2d5b32a37da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-0093000000-094c9e1bfbdeae11ab01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ll-1090000000-edf67d81c1d3829d273c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0094000000-c8b34837a6610be3fcbb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fz9-0490000000-914b8f387fe0cd72b097	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fxt-5930000000-35dd4033a8477f12cd44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-0098000000-5616871189dc97fa5f81	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0095000000-eba827a65da349366bb4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0600-3190000000-bf82fbc21d16e353611f	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1109.0	Log mg/kg	[620:2000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Acidic phospholipase A2 2	P15445	Naja naja	Predicted (SEA)	0.155698
Click to view 3D structure	Phospholipase A2, membrane associated	P14555	Humans	Predicted (SEA)	14.7135
Click to view 3D structure	Phospholipase A2	P00630	Apis mellifera	Predicted (SEA)	0.311397
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	593.367
Click to view 3D structure	ALK tyrosine kinase receptor	Q9UM73	Humans	Predicted (SEA)	4433.98
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	5561.86
Click to view 3D structure	Focal adhesion kinase 1	Q05397	Humans	Predicted (SEA)	4309.97
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	2713.36
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	3965.72
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	756.85
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	1447.45
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	4018.11
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	3447.09
Click to view 3D structure	Dual specificity protein phosphatase 3	P51452	Humans	Predicted (SEA)	1462.71
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	3089.52
Click to view 3D structure	3-oxoacyl-[acyl-carrier-protein] synthase 2	Q5TKS0	Staphylococcus aureus	Predicted (SEA)	1.08989
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	1084.67
Click to view 3D structure	D(1B) dopamine receptor	P21918	Humans	Predicted (SEA)	2794.4
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	1790.92
Click to view 3D structure	Kappa-type opioid receptor	P33534	Mus musculus	Predicted (SEA)	709.362
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	1081.64
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 2	P17706	Humans	Predicted (SEA)	1030.72
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	1858.73
Click to view 3D structure	Transient receptor potential cation channel subfamily A member 1	Q6RI86	Rattus norvegicus	Predicted (SEA)	910.602
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 2	Q9WUD2	Rattus norvegicus	Predicted (SEA)	124.637