ChemFOnt: Showing chemical card for 11b,13-Dihydrolactucin (CFc000283324)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:29 UTC

Chemfont ID

CFc000283324

Molecule Identification

Common Name

11b,13-Dihydrolactucin

Definition

11b,13-dihydrolactucin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 11b,13-dihydrolactucin can be found in a number of food items such as endive, chicory, dandelion, and romaine lettuce, which makes 11b,13-dihydrolactucin a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₅

Average Molecular Weight

292.327

Monoisotopic Molecular Weight

292.13107375

IUPAC Name

(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

83117-63-9

SMILES

[H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C

InChI Identifier

InChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1

InChI Key

AVVAXORRBBPMQM-YRRGMINMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303808)

Chicory (FooDB: FOOD00049)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Process

Not Available

Role

Biological role

Bitter (HMDB: HMDB0303808)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.69 g/L	ALOGPS
logP	0.38	ALOGPS
logP	0.22	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.46 m³·mol⁻¹	ChemAxon
Polarizability	30.09 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

HMDB0303808

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021725

KNApSAcK ID

Not Available

Chemspider ID

59696905

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 11b,13-Dihydrolactucin (CFc000283324)

MOL for CFc000283324 (11b,13-Dihydrolactucin)

3D MOL for CFc000283324 (11b,13-Dihydrolactucin)

3D SDF for CFc000283324 (11b,13-Dihydrolactucin)

3D-SDF for CFc000283324 (11b,13-Dihydrolactucin)

PDB for CFc000283324 (11b,13-Dihydrolactucin)

3D PDB for CFc000283324 (11b,13-Dihydrolactucin)

SMILES for CFc000283324 (11b,13-Dihydrolactucin)

INCHI for CFc000283324 (11b,13-Dihydrolactucin)

Structure for CFc000283324 (11b,13-Dihydrolactucin)

3D Structure for CFc000283324 (11b,13-Dihydrolactucin)