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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:11 UTC
Update Date2022-03-07 02:52:05 UTC
HMDB IDHMDB0029250
Secondary Accession Numbers
  • HMDB29250
Metabolite Identification
Common NamePigment A aglycone
DescriptionPigment A aglycone 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. Based on a literature review a significant number of articles have been published on Pigment A aglycone.
Structure
Data?1582753393
Synonyms
ValueSource
Malvidin 4-vinylphenolHMDB
Chemical FormulaC25H19O8
Average Molecular Weight447.4136
Monoisotopic Molecular Weight447.107992584
IUPAC Name4,11-dihydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxyphenyl)-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
Traditional Name4,11-dihydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxyphenyl)-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O)C1=CC=C(O)C=C1)=CC(O)=C2
InChI Identifier
InChI=1S/C25H18O8/c1-30-20-7-13(8-21(31-2)24(20)29)25-23(28)16-11-17(12-3-5-14(26)6-4-12)32-18-9-15(27)10-19(33-25)22(16)18/h3-11H,1-2H3,(H3-,26,27,28,29)/p+1
InChI KeyPDRWPABNSNPHHW-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3'-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP4.29ALOGPS
logP3.94ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity130.61 m³·mol⁻¹ChemAxon
Polarizability46.57 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.28331661259
DarkChem[M-H]-206.08631661259
DeepCCS[M+H]+201.69630932474
DeepCCS[M-H]-199.30130932474
DeepCCS[M-2H]-232.18430932474
DeepCCS[M+Na]+207.60930932474
AllCCS[M+H]+207.632859911
AllCCS[M+H-H2O]+205.032859911
AllCCS[M+NH4]+210.032859911
AllCCS[M+Na]+210.632859911
AllCCS[M-H]-202.732859911
AllCCS[M+Na-2H]-202.432859911
AllCCS[M+HCOO]-202.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pigment A aglyconeCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O)C1=CC=C(O)C=C1)=CC(O)=C26511.0Standard polar33892256
Pigment A aglyconeCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O)C1=CC=C(O)C=C1)=CC(O)=C24144.9Standard non polar33892256
Pigment A aglyconeCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1O)C1=CC=C(O)C=C1)=CC(O)=C24650.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pigment A aglycone,1TMS,isomer #1COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4421.0Semi standard non polar33892256
Pigment A aglycone,1TMS,isomer #2COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4495.4Semi standard non polar33892256
Pigment A aglycone,1TMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O4560.4Semi standard non polar33892256
Pigment A aglycone,1TMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4586.2Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #1COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4326.9Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #2COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4306.0Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4287.9Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4373.5Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #5COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O4315.0Semi standard non polar33892256
Pigment A aglycone,2TMS,isomer #6COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O4413.4Semi standard non polar33892256
Pigment A aglycone,3TMS,isomer #1COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4181.0Semi standard non polar33892256
Pigment A aglycone,3TMS,isomer #2COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4237.9Semi standard non polar33892256
Pigment A aglycone,3TMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4163.1Semi standard non polar33892256
Pigment A aglycone,3TMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O4262.7Semi standard non polar33892256
Pigment A aglycone,4TMS,isomer #1COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C4180.0Semi standard non polar33892256
Pigment A aglycone,1TBDMS,isomer #1COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4721.4Semi standard non polar33892256
Pigment A aglycone,1TBDMS,isomer #2COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4797.4Semi standard non polar33892256
Pigment A aglycone,1TBDMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O4821.0Semi standard non polar33892256
Pigment A aglycone,1TBDMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4835.2Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #1COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4878.0Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #2COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4859.3Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4861.6Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O4929.5Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #5COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O4898.4Semi standard non polar33892256
Pigment A aglycone,2TBDMS,isomer #6COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O4946.3Semi standard non polar33892256
Pigment A aglycone,3TBDMS,isomer #1COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4945.7Semi standard non polar33892256
Pigment A aglycone,3TBDMS,isomer #2COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C5003.8Semi standard non polar33892256
Pigment A aglycone,3TBDMS,isomer #3COC1=CC(C2=[O+]C3=CC(O)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C4936.4Semi standard non polar33892256
Pigment A aglycone,3TBDMS,isomer #4COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC4=C3C(=C2O[Si](C)(C)C(C)(C)C)C=C(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)O4)=CC(OC)=C1O5037.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pigment A aglycone GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0100900000-2de46ed3413f96eaae5b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pigment A aglycone GC-MS (3 TMS) - 70eV, Positivesplash10-0002-3400189000-7142d1be0e62cd2e20282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pigment A aglycone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 10V, Positive-QTOFsplash10-0002-0000900000-dfee557a2e7f6e674bb22016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 20V, Positive-QTOFsplash10-0005-0000900000-03b7fa91e4a697bc94cd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 40V, Positive-QTOFsplash10-0udi-1034900000-0f5e7b15f4076a6f45be2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 10V, Negative-QTOFsplash10-0002-0000900000-392e47a35869468f4e6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 20V, Negative-QTOFsplash10-0002-0000900000-42d1fb15eb6edbdee5ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 40V, Negative-QTOFsplash10-0pka-4006900000-326cb6b9c4bd11b37c462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 10V, Positive-QTOFsplash10-0002-0000900000-8d55cff30b9c0d22f3762021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 20V, Positive-QTOFsplash10-0002-0001900000-d036242f83c7c736dd672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pigment A aglycone 40V, Positive-QTOFsplash10-014i-0076900000-c2348c98829fd5b339482021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750825
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Pigment A aglycone → 6-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-11-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-yliumdetails
Pigment A aglycone → 11-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-hydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-yliumdetails
Pigment A aglycone → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)({4-[6,11-dihydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),4,6,9,11-pentaen-3-ylidene]cyclohexa-2,5-dien-1-ylidene})oxidaniumdetails
Pigment A aglycone → 7-{4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,5-dimethoxyphenyl}-6,11-dihydroxy-3-(4-hydroxyphenyl)-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-yliumdetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Pigment A aglycone → 4-[6,11-dihydroxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),4,6,9,11-pentaen-3-ylidene]cyclohexa-2,5-dien-1-ylidene hydrogen sulfuric acidiumdetails
Pigment A aglycone → (4-{7-[3,5-dimethoxy-4-(sulfooxy)phenyl]-6,11-dihydroxy-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),4,6,9,11-pentaen-3-ylidene}cyclohexa-2,5-dien-1-ylidene)oxidaniumdetails