ChemFOnt: Showing chemical card for 1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide (CFc000283292)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:25 UTC

Chemfont ID

CFc000283292

Molecule Identification

Common Name

1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide

Definition

1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide 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. 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide can be found in roman camomile, which makes 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₅

Average Molecular Weight

280.3163

Monoisotopic Molecular Weight

280.13107375

IUPAC Name

(9Z)-2,8-dihydroxy-4,9-dimethyl-14-methylidene-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-13-one

Traditional Name

(9Z)-2,8-dihydroxy-4,9-dimethyl-14-methylidene-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-13-one

CAS Registry Number

None

SMILES

C\C1=C\C2OC(=O)C(=C)C2C(O)CC2(C)OC2CC1O

InChI Identifier

InChI=1S/C15H20O5/c1-7-4-11-13(8(2)14(18)19-11)10(17)6-15(3)12(20-15)5-9(7)16/h4,9-13,16-17H,2,5-6H2,1,3H3/b7-4-

InChI Key

SCDDMRZFVFJIRF-DAXSKMNVSA-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
Sesquiterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303776)

Food

Herb and spice

Herb

Roman camomile (FooDB: FOOD00046)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0303776)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	12.4 g/L	ALOGPS
logP	0.26	ALOGPS
logP	0.19	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.71 m³·mol⁻¹	ChemAxon
Polarizability	28.92 Å³	ChemAxon
Number of Rings	3	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

HMDB0303776

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021648

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

157010104

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide (CFc000283292)

MOL for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

3D MOL for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

3D SDF for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

3D-SDF for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

PDB for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

3D PDB for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

SMILES for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

INCHI for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

Structure for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)

3D Structure for CFc000283292 (1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide)