ChemFOnt: Showing chemical card for 15-Hydroxy-3-dehydrodeoxyfruticin (CFc000282181)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:18 UTC

Chemfont ID

CFc000282181

Molecule Identification

Common Name

15-Hydroxy-3-dehydrodeoxyfruticin

Definition

15-hydroxy-3-dehydrodeoxyfruticin 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. 15-hydroxy-3-dehydrodeoxyfruticin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 15-hydroxy-3-dehydrodeoxyfruticin can be found in sunflower, which makes 15-hydroxy-3-dehydrodeoxyfruticin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-Hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,6H,9H,11ah-cyclodeca[b]furan-4-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₄O₇

Average Molecular Weight

376.405

Monoisotopic Molecular Weight

376.152203113

IUPAC Name

6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,6H,9H,11aH-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

Traditional Name

6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-3aH,4H,5H,11aH-cyclodeca[b]furan-4-yl 2-methylbut-2-enoate

CAS Registry Number

None

SMILES

CC=C(C)C(=O)OC1CC(C)(O)C=CC(=O)C(CO)=CC2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H24O7/c1-5-11(2)18(23)27-16-9-20(4,25)7-6-14(22)13(10-21)8-15-17(16)12(3)19(24)26-15/h5-8,15-17,21,25H,3,9-10H2,1-2,4H3

InChI Key

NEJKUCWBWUMARI-UHFFFAOYSA-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
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302665)

Food

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	0.83	ALOGPS
logP	1.83	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.62 m³·mol⁻¹	ChemAxon
Polarizability	38.74 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

External Links

HMDB ID

HMDB0302665

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005681

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 15-Hydroxy-3-dehydrodeoxyfruticin (CFc000282181)

MOL for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

3D MOL for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

3D SDF for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

3D-SDF for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

PDB for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

3D PDB for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

SMILES for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

INCHI for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

Structure for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)

3D Structure for CFc000282181 (15-Hydroxy-3-dehydrodeoxyfruticin)