PhytoHub: Showing entry for Malvidin-3-O-glucoside

Malvidin-3-O-glucoside

Identification

PhytoHub ID

PHUB001420

Name

Malvidin-3-O-glucoside

Systematic Name

Not Available

Synonyms

3,4',5,7-Tetrahydroxy-3',5'-dimethoxyflavylium(1+)
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenium-3-yl β-D-glucopyranoside
enin
Malvidin 3-glucoside
malvidin 3-O-β-D-glucoside

CAS Number

7228-78-6

Average Mass

493.44

Monoisotopic Mass

493.134052665

Chemical Formula

C₂₃H₂₅O₁₂

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

InChI Key

PXUQTDZNOHRWLI-OXUVVOBNSA-O

InChI Identifier

InChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1

SMILES

COC1=CC(=CC(OC)=C1O)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 3.70e-01 g/l
LogS (ALOGPS): -3.16
LogP (ALOGPS): 1.30
Hydrogen Acceptors: 12
Hydrogen Donors: 7
Rotatable Bond Count: 6
Polar Surface Area: 191.67
Refractivity: 127.20299999999999
Polarizability: 47.93269455076275
Formal Charge: 1
Physiological Charge: -1
pKa (strongest basic): -2.9810923799280262
pKa (strongest acidic): 6.3829279988198975
Number of Rings: 4
Rule of Five: No
Bioavailability: No
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: Yes

External Links

ChEBI: 6674
PubChem: 159287
Chemistry Dashboard: DTXSID30146622
KNApSAcK: C00020647
MetaboLights: MTBLC6674
Phenol-Explorer: 7
PeakForestCompound: 000868

Taxonomy as Food Phytochemical

Family: Polyphenols
Class: Flavonoids
Sub-class: Anthocyanins

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Flavonoids
Super-class: Phenylpropanoids and polyketides
Sub-class: Flavonoid glycosides
Direct Parent Name: Anthocyanidin-3-O-glycosides
Alternative Parent Names: ["1-benzopyrans", "1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "3'-O-methylated flavonoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Acetals", "Alkyl aryl ethers", "Anisoles", "Anthocyanidins", "Dimethoxybenzenes", "Flavonoid-3-O-glycosides", "Heteroaromatic compounds", "Hexoses", "Hydrocarbon derivatives", "Methoxyphenols", "O-glycosyl compounds", "Organic cations", "Oxacyclic compounds", "Oxanes", "Phenoxy compounds", "Polyols", "Primary alcohols", "Secondary alcohols"]
External Descriptor Annotations: ["Anthocyanidins", "Anthocyanidins and anthocyanins", "anthocyanin cation", "aromatic ether", "beta-D-glucoside"]
Substituent Names: ["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3p-methoxyflavonoid-skeleton", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Acetal", "Alcohol", "Alkyl aryl ether", "Anisole", "Anthocyanidin", "Anthocyanidin-3-o-glycoside", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Dimethoxybenzene", "Ether", "Flavonoid-3-o-glycoside", "Glycosyl compound", "Heteroaromatic compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxyflavonoid", "M-dimethoxybenzene", "Methoxybenzene", "Methoxyphenol", "Monocyclic benzene moiety", "Monosaccharide", "O-glycosyl compound", "Organic cation", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Phenol", "Phenol ether", "Phenoxy compound", "Polyol", "Primary alcohol", "Secondary alcohol"]

Spectra from Online Resources

No spectra information available

Food Sources

Name	Group
Blueberry	Fruit, Berries	Publications	Show
Grapes	Fruit, Berries		Show
Red raspberry	Fruit, Berries		Show
Red wine	Beverages, Alcoholic		Show
White wine	Beverages, Alcoholic		Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food Phytochemical	Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
Malvidin-3-O-glucoside	Syringic acid	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₉H₁₀O₅	198.052823422		Publications
Malvidin-3-O-glucoside	Curcumin	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₁H₂₀O₆	368.125988364	Detailed Intervention Studies
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	human	plasma, urine	unchanged	1h-3h	20-50 nmol/L	<1%	C₂₃H₂₅O₁₂	493.134052665	Detailed Intervention Studies	Publications
Malvidin-3-O-glucoside	Syringic acid-4-O-glucuronide	Not Available	Not Available	host metabolism	Not Available	Not Available	Not Available	C₁₅H₁₈O₁₁	374.0849114
Malvidin-3-O-glucoside	Malvidin	in vitro (human) in vitro (pig)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₇H₁₅O₇	331.081229243		Publications
Malvidin-3-O-glucoside	Malvidin 3-O-glucoside	Not Available	Not Available	Not Available	Not Available	Not Available	Not Available	C₂₃H₂₅O₁₂	493.134052665	Detailed Intervention Studies

Inter-Individual Variations in Metabolism

Food Phytochemical	Metabolite	Effect	Value
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Age	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Bmi	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Ethnicity	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Genotype	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Health_status	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Microbiota	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Sex	Not studied
Malvidin-3-O-glucoside	Malvidin-3-O-glucoside	Smoking	Not studied

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Showing entry for Malvidin-3-O-glucoside