Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:55:45 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034133
Secondary Accession Numbers
  • HMDB34133
Metabolite Identification
Common Name3-(1,1-Dimethylallyl)scopoletin
Description3-(1,1-Dimethylallyl)scopoletin belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 3-(1,1-Dimethylallyl)scopoletin has been detected, but not quantified in, herbs and spices. This could make 3-(1,1-dimethylallyl)scopoletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(1,1-Dimethylallyl)scopoletin.
Structure
Data?1563862516
Synonyms
ValueSource
3-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-oneHMDB
Chemical FormulaC15H16O4
Average Molecular Weight260.2851
Monoisotopic Molecular Weight260.104859
IUPAC Name7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one
Traditional Name7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one
CAS Registry Number19723-23-0
SMILES
COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O
InChI Identifier
InChI=1S/C15H16O4/c1-5-15(2,3)10-6-9-7-13(18-4)11(16)8-12(9)19-14(10)17/h5-8,16H,1H2,2-4H3
InChI KeyNEUWPSXOYGGGFO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Point132 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.6ALOGPS
logP2.89ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.23ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.62 m³·mol⁻¹ChemAxon
Polarizability27.44 ųChemAxon
Number of Rings2ChemAxon
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]+161.84631661259
DarkChem[M-H]-162.72631661259
DeepCCS[M+H]+161.10730932474
DeepCCS[M-H]-158.74930932474
DeepCCS[M-2H]-191.90730932474
DeepCCS[M+Na]+167.20130932474
AllCCS[M+H]+157.432859911
AllCCS[M+H-H2O]+153.632859911
AllCCS[M+NH4]+161.032859911
AllCCS[M+Na]+162.032859911
AllCCS[M-H]-162.432859911
AllCCS[M+Na-2H]-162.132859911
AllCCS[M+HCOO]-161.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(1,1-Dimethylallyl)scopoletinCOC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O2991.1Standard polar33892256
3-(1,1-Dimethylallyl)scopoletinCOC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O2219.4Standard non polar33892256
3-(1,1-Dimethylallyl)scopoletinCOC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O2259.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-(1,1-Dimethylallyl)scopoletin,1TMS,isomer #1C=CC(C)(C)C1=CC2=CC(OC)=C(O[Si](C)(C)C)C=C2OC1=O2355.8Semi standard non polar33892256
3-(1,1-Dimethylallyl)scopoletin,1TBDMS,isomer #1C=CC(C)(C)C1=CC2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O2600.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gea-1290000000-ffcc20d45eed116243752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-4097000000-71d3030ec77ac06d0cc32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 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 - 3-(1,1-Dimethylallyl)scopoletin 10V, Positive-QTOFsplash10-03di-0090000000-57f6133e534c1e2efefc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Positive-QTOFsplash10-02t9-6090000000-6daadd055cecbf1f0e4a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Positive-QTOFsplash10-014i-9240000000-65dd2878539e6d9f22c02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Negative-QTOFsplash10-0a4i-0090000000-7a17be0d67edef9921db2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Negative-QTOFsplash10-0a4i-0290000000-090da48a719b8c00882f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Negative-QTOFsplash10-014v-2940000000-4ccf496faed16016a18b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Negative-QTOFsplash10-0a4i-0090000000-07597ad49430bb51c2462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Negative-QTOFsplash10-0690-0190000000-4a73bd762df5e781c79d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Negative-QTOFsplash10-002b-0950000000-81779eb4ca958f33f60d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Positive-QTOFsplash10-03di-0190000000-e4770cf17e3d89a593ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Positive-QTOFsplash10-03ei-0190000000-2bff7da49954f2b027e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Positive-QTOFsplash10-014i-1490000000-ae2b3313ba2faf4d54732021-09-22Wishart 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 IDFDB012407
KNApSAcK IDNot Available
Chemspider ID4526592
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5377569
PDB IDNot Available
ChEBI ID174419
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:
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
3-(1,1-Dimethylallyl)scopoletin → 3,4,5-trihydroxy-6-{[6-methoxy-3-(2-methylbut-3-en-2-yl)-2-oxo-2H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails