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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:45 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030581
Secondary Accession Numbers
  • HMDB30581
Metabolite Identification
Common NamePerillanin
DescriptionPerillanin belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Based on a literature review very few articles have been published on Perillanin.
Structure
Data?1563862007
Synonyms
ValueSource
Cyanidin 3-(6-P-coumaroylglucoside)-5-glucosideHMDB
ShisoninHMDB
Shisonin bHMDB
Chemical FormulaC36H37O18
Average Molecular Weight757.6682
Monoisotopic Molecular Weight757.19798938
IUPAC Name2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
CAS Registry Number23410-80-2
SMILES
OCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(COC(=O)\C=C\C5=CC=C(O)C=C5)C(O)C(O)C4O)C=C23)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C36H36O18/c37-13-25-28(43)30(45)32(47)35(53-25)51-23-11-18(39)10-22-19(23)12-24(34(50-22)16-4-7-20(40)21(41)9-16)52-36-33(48)31(46)29(44)26(54-36)14-49-27(42)8-3-15-1-5-17(38)6-2-15/h1-12,25-26,28-33,35-37,43-48H,13-14H2,(H3-,38,39,40,41,42)/p+1
InChI KeyYPXWWSJGANMFFQ-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin 3-O-6-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Anthocyanidin 3-o-6-p-coumaroyl-glycoside
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Anthocyanin
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.2 g/LALOGPS
logP1.79ALOGPS
logP1.14ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area298.89 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity189.95 m³·mol⁻¹ChemAxon
Polarizability72.28 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-292.28130932474
DeepCCS[M+Na]+266.67130932474
AllCCS[M+H]+256.332859911
AllCCS[M+H-H2O]+256.032859911
AllCCS[M+NH4]+256.532859911
AllCCS[M+Na]+256.632859911
AllCCS[M-H]-248.732859911
AllCCS[M+Na-2H]-252.532859911
AllCCS[M+HCOO]-256.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PerillaninOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(COC(=O)\C=C\C5=CC=C(O)C=C5)C(O)C(O)C4O)C=C23)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O8355.2Standard polar33892256
PerillaninOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(COC(=O)\C=C\C5=CC=C(O)C=C5)C(O)C(O)C4O)C=C23)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O6356.4Standard non polar33892256
PerillaninOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(COC(=O)\C=C\C5=CC=C(O)C=C5)C(O)C(O)C4O)C=C23)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O7298.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Perillanin GC-MS (TBDMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 10V, Positive-QTOFsplash10-0a4i-0100000900-ace4f9c4925dce91a9512016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 20V, Positive-QTOFsplash10-014j-1200000900-7e03f86c3af54e976d492016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 40V, Positive-QTOFsplash10-01ot-6900001200-ca000739b87b9de3a7662016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 10V, Negative-QTOFsplash10-0a4i-1200000900-3c89fb94c5e49efd09ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 20V, Negative-QTOFsplash10-0bt9-5700000900-4707c7b3c6404941663e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 40V, Negative-QTOFsplash10-052f-9200000000-6311d167ce6ed2a315962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 10V, Positive-QTOFsplash10-0f72-0430920300-95a133490a1c787241662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 20V, Positive-QTOFsplash10-000j-0481932400-e82686f5151ff9ec1fe52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Perillanin 40V, Positive-QTOFsplash10-014j-0910120100-76453344e1020c54d2b12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDC00006819
Chemspider ID24842204
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44256762
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Perillanin → 2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-yliumdetails