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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:28:27 UTC
Update Date2022-03-07 02:54:31 UTC
HMDB IDHMDB0035479
Secondary Accession Numbers
  • HMDB35479
Metabolite Identification
Common NameIsolicopyranocoumarin
DescriptionIsolicopyranocoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Isolicopyranocoumarin has been detected, but not quantified in, herbs and spices. This could make isolicopyranocoumarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isolicopyranocoumarin.
Structure
Data?1563862726
SynonymsNot Available
Chemical FormulaC21H20O7
Average Molecular Weight384.3793
Monoisotopic Molecular Weight384.120902994
IUPAC Name3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8,8-dimethyl-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one
Traditional Name3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8,8-dimethyl-6H,7H-pyrano[3,2-g]chromen-2-one
CAS Registry Number197303-94-9
SMILES
COC1=C2C=C(C(=O)OC2=CC2=C1CC(O)C(C)(C)O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O7/c1-21(2)18(24)8-14-17(28-21)9-16-13(19(14)26-3)7-12(20(25)27-16)11-5-4-10(22)6-15(11)23/h4-7,9,18,22-24H,8H2,1-3H3
InChI KeyJHGBGRLHQJNGPN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassHydroxyisoflavonoids
Direct ParentHydroxyisoflavonoids
Alternative Parents
Substituents
  • Isoflav-3-enone skeleton
  • Hydroxyisoflavonoid
  • Pyranocoumarin
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Coumarin
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point251 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility216.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP2.91ALOGPS
logP2.64ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.22 m³·mol⁻¹ChemAxon
Polarizability39.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.54331661259
DarkChem[M-H]-189.72431661259
DeepCCS[M+H]+189.74830932474
DeepCCS[M-H]-187.3930932474
DeepCCS[M-2H]-221.15630932474
DeepCCS[M+Na]+196.20930932474
AllCCS[M+H]+191.932859911
AllCCS[M+H-H2O]+189.032859911
AllCCS[M+NH4]+194.732859911
AllCCS[M+Na]+195.532859911
AllCCS[M-H]-194.332859911
AllCCS[M+Na-2H]-194.232859911
AllCCS[M+HCOO]-194.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsolicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CC(O)C(C)(C)O2)C1=C(O)C=C(O)C=C14463.6Standard polar33892256
IsolicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CC(O)C(C)(C)O2)C1=C(O)C=C(O)C=C13359.9Standard non polar33892256
IsolicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CC(O)C(C)(C)O2)C1=C(O)C=C(O)C=C13791.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isolicopyranocoumarin,1TMS,isomer #1COC1=C2CC(O[Si](C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23379.9Semi standard non polar33892256
Isolicopyranocoumarin,1TMS,isomer #2COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23310.2Semi standard non polar33892256
Isolicopyranocoumarin,1TMS,isomer #3COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23343.8Semi standard non polar33892256
Isolicopyranocoumarin,2TMS,isomer #1COC1=C2CC(O[Si](C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23256.4Semi standard non polar33892256
Isolicopyranocoumarin,2TMS,isomer #2COC1=C2CC(O[Si](C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23237.1Semi standard non polar33892256
Isolicopyranocoumarin,2TMS,isomer #3COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23273.8Semi standard non polar33892256
Isolicopyranocoumarin,3TMS,isomer #1COC1=C2CC(O[Si](C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23225.1Semi standard non polar33892256
Isolicopyranocoumarin,1TBDMS,isomer #1COC1=C2CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23623.6Semi standard non polar33892256
Isolicopyranocoumarin,1TBDMS,isomer #2COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23529.6Semi standard non polar33892256
Isolicopyranocoumarin,1TBDMS,isomer #3COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23575.3Semi standard non polar33892256
Isolicopyranocoumarin,2TBDMS,isomer #1COC1=C2CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23697.4Semi standard non polar33892256
Isolicopyranocoumarin,2TBDMS,isomer #2COC1=C2CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23645.6Semi standard non polar33892256
Isolicopyranocoumarin,2TBDMS,isomer #3COC1=C2CC(O)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23681.1Semi standard non polar33892256
Isolicopyranocoumarin,3TBDMS,isomer #1COC1=C2CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23804.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isolicopyranocoumarin GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-0019000000-7ac2d294f9f8b1dad96e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isolicopyranocoumarin GC-MS (3 TMS) - 70eV, Positivesplash10-000i-3010090000-13d18754c6bf2ba6c2122017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isolicopyranocoumarin 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 - Isolicopyranocoumarin 10V, Positive-QTOFsplash10-000i-0009000000-849011a5f4672c239b642016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 20V, Positive-QTOFsplash10-03di-0009000000-5d63bd1f37603096dfa02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 40V, Positive-QTOFsplash10-00n0-5197000000-ed2136f6dd35123ea2872016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 10V, Negative-QTOFsplash10-001i-0009000000-803d3ca6f0d7f20497d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 20V, Negative-QTOFsplash10-0230-6229000000-6d6fa8fc5d6b2e84c4a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 40V, Negative-QTOFsplash10-0a59-5491000000-2e1b224c6d954f3123c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 10V, Positive-QTOFsplash10-000i-0009000000-97ce302200d2a34352d52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 20V, Positive-QTOFsplash10-00kr-0009000000-037959858be9385d3f512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 40V, Positive-QTOFsplash10-03y0-0019000000-59fd4b65852bf675ae682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 10V, Negative-QTOFsplash10-001i-0009000000-d07d1bbe498d0feb188e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 20V, Negative-QTOFsplash10-0f89-0019000000-65d6dea52426710388842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isolicopyranocoumarin 40V, Negative-QTOFsplash10-0f80-0139000000-57623059db82e485686e2021-09-24Wishart 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 IDFDB014165
KNApSAcK IDNot Available
Chemspider ID8985345
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10810040
PDB IDNot Available
ChEBI ID175894
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1850071
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:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Isolicopyranocoumarin → [7-(2,4-dihydroxyphenyl)-5-methoxy-2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl]oxidanesulfonic aciddetails
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
Isolicopyranocoumarin → 3,4,5-trihydroxy-6-(3-hydroxy-4-{7-hydroxy-5-methoxy-8,8-dimethyl-2-oxo-2H,6H,7H,8H-pyrano[3,2-g]chromen-3-yl}phenoxy)oxane-2-carboxylic aciddetails
Isolicopyranocoumarin → 3,4,5-trihydroxy-6-(5-hydroxy-2-{7-hydroxy-5-methoxy-8,8-dimethyl-2-oxo-2H,6H,7H,8H-pyrano[3,2-g]chromen-3-yl}phenoxy)oxane-2-carboxylic aciddetails