ChemFOnt: Showing chemical card for Lappaphen A (CFc000281834)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:36 UTC

Chemfont ID

CFc000281834

Molecule Identification

Common Name

Lappaphen A

Definition

Lappaphen b belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Lappaphen b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Lappaphen b can be found in burdock, which makes lappaphen b a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆O₄S₂

Average Molecular Weight

478.623

Monoisotopic Molecular Weight

478.1272507

IUPAC Name

3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

None

SMILES

CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=O

InChI Identifier

InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3

InChI Key

WKQBNYGTPIGLMV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Bithiophene
Aryl alkyl ketone
Aryl ketone
2,5-disubstituted thiophene
Beta-hydroxy ketone
Gamma butyrolactone
Heteroaromatic compound
Thiophene
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302318)

Food

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.96	ALOGPS
logP	5.56	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.71 m³·mol⁻¹	ChemAxon
Polarizability	52.85 Å³	ChemAxon
Number of Rings	5	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

HMDB0302318

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004114

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

13856335

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Lappaphen A (CFc000281834)

MOL for CFc000281834 (Lappaphen A)

3D MOL for CFc000281834 (Lappaphen A)

3D SDF for CFc000281834 (Lappaphen A)

3D-SDF for CFc000281834 (Lappaphen A)

PDB for CFc000281834 (Lappaphen A)

3D PDB for CFc000281834 (Lappaphen A)

SMILES for CFc000281834 (Lappaphen A)

INCHI for CFc000281834 (Lappaphen A)

Structure for CFc000281834 (Lappaphen A)

3D Structure for CFc000281834 (Lappaphen A)