ChemFOnt: Showing chemical card for Obacunone 17-O-beta-D-glucoside (CFc000282058)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:03 UTC

Chemfont ID

CFc000282058

Molecule Identification

Common Name

Obacunone 17-O-beta-D-glucoside

Definition

Obacunone 17-o-beta-d-glucoside is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Obacunone 17-o-beta-d-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Obacunone 17-o-beta-d-glucoside can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes obacunone 17-o-beta-d-glucoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-[(Furan-3-yl)({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylate	Generator
Obacunone 17-O-b-D-glucoside	Generator
Obacunone 17-O-β-D-glucoside	Generator

Chemical Formula

C₃₂H₄₂O₁₃

Average Molecular Weight

634.6681

Monoisotopic Molecular Weight

634.26254143

IUPAC Name

9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

Traditional Name

9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-6,10,11,11a-tetrahydro-5aH-spiro[naphtho[2,1-c]oxepine-8,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

None

SMILES

CC1(CCC2C3(C)C=CC(=O)OC(C)(C)C3CC(=O)C2(C)C11OC1C(O)=O)C(OC1OC(CO)C(O)C(O)C1O)C1=COC=C1

InChI Identifier

InChI=1S/C32H42O13/c1-28(2)18-12-19(34)31(5)17(29(18,3)9-7-20(35)44-28)6-10-30(4,32(31)25(45-32)26(39)40)24(15-8-11-41-14-15)43-27-23(38)22(37)21(36)16(13-33)42-27/h7-9,11,14,16-18,21-25,27,33,36-38H,6,10,12-13H2,1-5H3,(H,39,40)

InChI Key

MXZVBPOYCKIXHN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Acetal
Oxirane
Ether
Carbonyl group
Primary alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302542)

Food

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.45	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	205.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	152.09 m³·mol⁻¹	ChemAxon
Polarizability	63.57 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302542

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005061

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

14313526

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Obacunone 17-O-beta-D-glucoside (CFc000282058)

MOL for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

3D MOL for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

3D SDF for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

3D-SDF for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

PDB for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

3D PDB for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

SMILES for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

INCHI for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

Structure for CFc000282058 (Obacunone 17-O-beta-D-glucoside)

3D Structure for CFc000282058 (Obacunone 17-O-beta-D-glucoside)