MiMeDB: Showing metabocard for Malvidin (MMDBc0033669)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:58:14 UTC

Update Date

2022-12-15 22:51:57 UTC

Metabolite ID

MMDBc0033669

Metabolite Identification

Common Name

Malvidin

Description

Malvidin is an anthocyanin. Anthocyanins are pigments that give color red to red grape (Vitis vinifera) varieties, and blood oranges (Citrus sinensis (L.) Osbeck). (PMID: 15563216 , 17425943 ). Anthocyanins have potentially chemopreventive activity, apart from its antioxidant activity. (PMID: 16080535 ). Numerous classes of grape anthocyanins are transferred to the wine and confer taste and color to the beverage. (PMID: 15954164 ). Anthocyanins are water soluble pigments belonging to the flavonoids compound family involved in nature in a wide range of functions such as flowers, fruits, and seeds pigmentation to attract pollinators, to disperse seeds, to protect against UV light damage, and in plant defense to protect against pathogen attack. Because anthocyanins impart much of the color and flavor of fruits and vegetables, they are usually components of the human diet and are not only considered exclusively as food products but also as therapeutic agents; in fact, anthocyanins have been suggested to protect against oxidative stress, coronary heart diseases, certain cancers, and other age-related diseases. At least part of these presumed health-promoting features can be attributed to the antioxidant properties of these compounds whose chemical structure appears ideal for free radical scavenging. (PMID: 16277406 ). Malvidin is a biomarker for the consumption of blueberries.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309171710052D          

 24 26  0  0  0  0            999 V2000
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 15  4  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 12  2  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  1  0  0  0  0
 22  1  1  0  0  0  0
 22 14  1  0  0  0  0
 23  2  1  0  0  0  0
 23 15  1  0  0  0  0
 24 13  2  0  0  0  0
 24 17  1  0  0  0  0
M  CHG  1  24   1
M  END
> <DATABASE_ID>
MMDBc0033669

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1

> <INCHI_KEY>
KZMACGJDUUWFCH-UHFFFAOYSA-O

> <FORMULA>
C17H15O7

> <MOLECULAR_WEIGHT>
331.2968

> <EXACT_MASS>
331.081777834

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.09069402984694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.8293

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.7981259163212355

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.988279410536358

> <JCHEM_PKA_STRONGEST_BASIC>
-4.612156909893124

> <JCHEM_POLAR_SURFACE_AREA>
112.52000000000001

> <JCHEM_REFRACTIVITY>
95.05859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-17         0                                  
HETATM    1  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+1
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    8   14                                                       
CONECT    4    8   15                                                       
CONECT    5    9   11                                                       
CONECT    6    9   13                                                       
CONECT    7   10   12                                                       
CONECT    8    3    4   17                                                  
CONECT    9    5    6   18                                                  
CONECT   10    7   11   13                                                  
CONECT   11    5   10   19                                                  
CONECT   12    7   17   20                                                  
CONECT   13    6   10   24                                                  
CONECT   14    3   16   22                                                  
CONECT   15    4   16   23                                                  
CONECT   16   14   15   21                                                  
CONECT   17    8   12   24                                                  
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22    1   14                                                       
CONECT   23    2   15                                                       
CONECT   24   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

Synonyms

Value	Source
3',5'-Dimethoxy-3,4',5,7-tetrahydroxyflavylium acid anion	ChEBI
Malvidin chloride	Kegg

Molecular Formula

C₁₇H₁₅O₇

Average Mass

331.2968

Monoisotopic Mass

331.081777834

IUPAC Name

3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium

CAS Registry Number

643-84-5

SMILES

COC1=CC(=CC(OC)=C1O)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1

InChI Identifier

InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1

InChI Key

KZMACGJDUUWFCH-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
M-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:6674 )
Anthocyanidins (C08716 )
Anthocyanidins and anthocyanins (C08716 )
Anthocyanidins (LMPK12010004 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	1.98	ALOGPS
logP	2.83	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	5.99	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	112.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.06 m³·mol⁻¹	ChemAxon
Polarizability	33.09 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002713

KNApSAcK ID

C00020647

Chemspider ID

Not Available

KEGG Compound ID

C08716

BioCyc ID

CPD-15051

BiGG ID

Not Available

Wikipedia Link

Malvidin

METLIN ID

Not Available

PubChem Compound

159287

PDB ID

Not Available

ChEBI ID

6674

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Linseisen J, Radtke J, Wolfram G: [Flavonoid intake of adults in a Bavarian subgroup of the national food consumption survey]. Z Ernahrungswiss. 1997 Dec;36(4):403-12. doi: 10.1007/BF01617836. [PubMed:9467240 ]
Hillebrand S, Schwarz M, Winterhalter P: Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. J Agric Food Chem. 2004 Dec 1;52(24):7331-8. doi: 10.1021/jf0487957. [PubMed:15563216 ]
Flamini R: Some advances in the knowledge of grape, wine and distillates chemistry as achieved by mass spectrometry. J Mass Spectrom. 2005 Jun;40(6):705-13. doi: 10.1002/jms.887. [PubMed:15954164 ]
Fimognari C, Berti F, Nusse M, Cantelli-Fortii G, Hrelia P: In vitro anticancer activity of cyanidin-3-O-beta-glucopyranoside: effects on transformed and non-transformed T lymphocytes. Anticancer Res. 2005 Jul-Aug;25(4):2837-40. [PubMed:16080535 ]
Lo Piero AR, Puglisi I, Rapisarda P, Petrone G: Anthocyanins accumulation and related gene expression in red orange fruit induced by low temperature storage. J Agric Food Chem. 2005 Nov 16;53(23):9083-8. doi: 10.1021/jf051609s. [PubMed:16277406 ]
Bovell-Benjamin AC: Sweet potato: a review of its past, present, and future role in human nutrition. Adv Food Nutr Res. 2007;52:1-59. doi: 10.1016/S1043-4526(06)52001-7. [PubMed:17425943 ]

Showing metabocard for Malvidin (MMDBc0033669)

MOL for #<Metabolite:0x0000560bde102530>

3D MOL for #<Metabolite:0x0000560bde102530>

3D SDF for #<Metabolite:0x0000560bde102530>

3D-SDF for #<Metabolite:0x0000560bde102530>

PDB for #<Metabolite:0x0000560bde102530>

3D PDB for #<Metabolite:0x0000560bde102530>

SMILES for #<Metabolite:0x0000560bde102530>

INCHI for #<Metabolite:0x0000560bde102530>

Structure for #<Metabolite:0x0000560bde102530>

3D Structure for #<Metabolite:0x0000560bde102530>