Showing chemical card for Apigenin 7-O-beta-D-rutinoside (CFc000282665)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:14 UTC

Chemfont ID

CFc000282665

Molecule Identification

Common Name

Apigenin 7-O-beta-D-rutinoside

Definition

Apigenin 7-o-beta-d-rutinoside, also known as rhoifolin or apigenin-7-O-rhamnoglucoside, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apigenin 7-o-beta-d-rutinoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 7-o-beta-d-rutinoside can be found in carrot, orange mint, and wild carrot, which makes apigenin 7-o-beta-d-rutinoside a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000282665 (Apigenin 7-O-beta-D-rutinoside)

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

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INCHI for CFc000282665 (Apigenin 7-O-beta-D-rutinoside)

InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

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Structure for CFc000282665 (Apigenin 7-O-beta-D-rutinoside)

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3D Structure for CFc000282665 (Apigenin 7-O-beta-D-rutinoside)

Synonyms

Value	Source
7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	ChEBI
Apigenin-7-O-rhamnoglucoside	ChEBI
Rhoifolin	ChEBI
Rhoifoloside	ChEBI
7-((2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	Generator
7-((2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	Generator
Apigenin 7-O-b-D-rutinoside	Generator
Apigenin 7-O-β-D-rutinoside	Generator

Chemical Formula

C₂₇H₃₀O₁₄

Average Molecular Weight

578.5187

Monoisotopic Molecular Weight

578.163555668

IUPAC Name

7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

rhoifolin

CAS Registry Number

17306-46-6

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC3=C(C(O)=C2)C(=O)C=C(O3)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI Key

RPMNUQRUHXIGHK-PYXJVEIZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

4'-hydroxyflavonoids
5-hydroxyflavonoids
Flavones
Phenolic glycosides
Chromones
Disaccharides
O-glycosyl compounds
1-hydroxy-2-unsubstituted benzenoids
1-hydroxy-4-unsubstituted benzenoids
Pyranones and derivatives
Benzene and substituted derivatives
Oxanes
Vinylogous acids
Heteroaromatic compounds
Secondary alcohols
Oxacyclic compounds
Acetals
Polyols
Organic oxides
Primary alcohols
Hydrocarbon derivatives

Substituents

Flavonoid-7-o-glycoside
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
Disaccharide
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:31227 )
dihydroxyflavone (CHEBI:31227 )
glycosyloxyflavone (CHEBI:31227 )
neohesperidoside (CHEBI:31227 )
flavones (C12627 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303149)

Food

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Herb and spice

Herb

Orange mint (FooDB: FOOD00110)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.55 g/L	ALOGPS
logP	0	ALOGPS
logP	-0.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.93 m³·mol⁻¹	ChemAxon
Polarizability	56.74 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon