ChemFOnt: Showing chemical card for Arctiopicrin (CFc000281373)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:41 UTC

Chemfont ID

CFc000281373

Molecule Identification

Common Name

Arctiopicrin

Definition

Arctiopicrin belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Arctiopicrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Arctiopicrin can be found in burdock, which makes arctiopicrin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₆

Average Molecular Weight

350.4061

Monoisotopic Molecular Weight

350.172938564

IUPAC Name

(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylpropanoate

Traditional Name

arctiopicrin

CAS Registry Number

19889-01-1

SMILES

CC(CO)C(=O)O[C@H]1C\C(C)=C\CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H26O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,12,15-17,20-21H,3-4,6-7,9-10H2,1-2H3/b11-5+,14-8-/t12?,15-,16+,17+/m0/s1

InChI Key

VOOFFTMORIBISQ-UMRVURNHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:2810 )
Germacrenes (C09297 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301857)

Food

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antibiotic (HMDB: HMDB0301857)
Gram(+)icide (HMDB: HMDB0301857)

Agriculture

Pesticide (HMDB: HMDB0301857)

Biological role

Bitter (HMDB: HMDB0301857)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.59	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.42 m³·mol⁻¹	ChemAxon
Polarizability	36.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon