PhytoHub: Showing entry for Malvidin 3-O-arabinoside

Malvidin 3-O-arabinoside

Identification

PhytoHub ID

PHUB001631

Name

Malvidin 3-O-arabinoside

Systematic Name

Not Available

Synonyms

(2S,3R,4S,5S)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxyoxane-3,4,5-tri
3,4',5,7-Tetrahydroxy-3',5'-dimethoxyflavylium(1+); 3-O-α-L-Arabinopyranoside
Malvidin 3-arabinoside

CAS Number

785047-89-4, 28500-04-1

Average Mass

463.414

Monoisotopic Mass

463.123487981

Chemical Formula

C₂₂H₂₃O₁₁

IUPAC Name

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

InChI Key

ZWAAFZOEMBEAAF-YGUHJOONSA-O

InChI Identifier

InChI=1S/C22H22O11/c1-29-15-3-9(4-16(30-2)19(15)27)21-17(33-22-20(28)18(26)13(25)8-31-22)7-11-12(24)5-10(23)6-14(11)32-21/h3-7,13,18,20,22,25-26,28H,8H2,1-2H3,(H2-,23,24,27)/p+1/t13-,18-,20+,22+/m0/s1

SMILES

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

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 2.63e-01 g/l
LogS (ALOGPS): -3.28
LogP (ALOGPS): 1.61
Hydrogen Acceptors: 11
Hydrogen Donors: 6
Rotatable Bond Count: 5
Polar Surface Area: 171.44
Refractivity: 121.24049999999998
Polarizability: 44.88419256010853
Formal Charge: 1
Physiological Charge: -1
pKa (strongest basic): -3.5265985690834403
pKa (strongest acidic): 6.382931287057645
Number of Rings: 4
Rule of Five: No
Bioavailability: No
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

No external links

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: Flavonoid-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", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Methoxyphenols", "Monosaccharides", "O-glycosyl compounds", "Organic cations", "Oxacyclic compounds", "Oxanes", "Phenoxy compounds", "Polyols", "Secondary alcohols"]
External Descriptor Annotations: Not Available
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", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Dimethoxybenzene", "Ether", "Flavonoid-3-o-glycoside", "Glycosyl compound", "Heteroaromatic compound", "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", "Secondary alcohol"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(313.0706646,9.023340527);(315.0863146,8.459311558);(317.1019647,2.310019772);(329.0655792,9.515622051);(331.0812292,32.48974551);(333.0968793,3.477780471);(445.1129233,6.583177885);(463.123488,8.857046104)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(123.0440559,1.808960203);(133.0495352,2.855314938);(153.0546206,2.871850242);(299.0550145,1.954265344);(301.0706646,6.995378441);(303.0863146,12.72645098);(305.1019647,3.222151121);(313.0706646,3.885664568);(315.0863146,6.539255407);(317.0655792,2.859968722);(329.0655792,2.157938083);(331.0812292,24.74934582);(333.0968793,8.243364269)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(51.02292652,0.7638716102);(55.01784114,1.629349876);(71.01275576,0.8038837526);(73.02840582,1.40974818);(115.0389705,0.9200274548);(117.0546206,0.8510804148);(121.0284058,6.275106193);(123.0440559,6.67403328);(133.0495352,0.8195425196);(137.0233204,4.690609311);(139.0389705,2.059085329);(153.0546206,5.120373966);(165.0546206,1.711782877);(179.0338851,2.218368451);(181.0495352,1.054571283);(241.0495352,1.461319266);(243.0651853,1.27772895);(247.0600999,1.122675964);(257.0444498,4.910412114);(259.0600999,6.088726145);(289.0706646,1.303666624);(299.0550145,1.51997644);(301.0706646,3.126118888);(303.0863146,2.194959991);(313.0706646,5.30640506);(315.0499291,0.9639110286);(315.0863146,2.578680507);(317.0655792,1.082709018);(329.0655792,1.009767266);(331.0812292,3.864242349);(403.1023586,0.8536179658)

Food Sources

	Name	Group
	Blueberry	Fruit, Berries	Publications	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-arabinoside		Malvidin 3-O-arabinoside	human	plasma, urine	unchanged	1h-3h	<20 nmol/L	<1%	C₂₂H₂₃O₁₁	463.123487981	Detailed Intervention Studies	Publications

Inter-Individual Variations in Metabolism

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

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Showing entry for Malvidin 3-O-arabinoside