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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:25 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030853
Secondary Accession Numbers
  • HMDB30853
Metabolite Identification
Common Name(R)-Meranzin
Description(R)-Meranzin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one) (R)-Meranzin is a bitter tasting compound (R)-Meranzin has been detected, but not quantified in, sweet oranges (Citrus sinensis). This could make (R)-meranzin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-Meranzin.
Structure
Data?1563862048
SynonymsNot Available
Chemical FormulaC15H16O4
Average Molecular Weight260.2851
Monoisotopic Molecular Weight260.104859
IUPAC Name8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxy-2H-chromen-2-one
Traditional Name8-[(3,3-dimethyloxiran-2-yl)methyl]-7-methoxychromen-2-one
CAS Registry NumberNot Available
SMILES
COC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C15H16O4/c1-15(2)12(19-15)8-10-11(17-3)6-4-9-5-7-13(16)18-14(9)10/h4-7,12H,8H2,1-3H3
InChI KeyLSZONYLDFHGRDP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point98 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP2.93ALOGPS
logP2.38ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity71.09 m³·mol⁻¹ChemAxon
Polarizability27.33 ųChemAxon
Number of Rings3ChemAxon
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]+160.42531661259
DarkChem[M-H]-158.73131661259
DeepCCS[M+H]+166.85630932474
DeepCCS[M-H]-164.49830932474
DeepCCS[M-2H]-197.38430932474
DeepCCS[M+Na]+172.94930932474
AllCCS[M+H]+158.432859911
AllCCS[M+H-H2O]+154.532859911
AllCCS[M+NH4]+162.132859911
AllCCS[M+Na]+163.132859911
AllCCS[M-H]-165.032859911
AllCCS[M+Na-2H]-164.732859911
AllCCS[M+HCOO]-164.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-MeranzinCOC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C12885.9Standard polar33892256
(R)-MeranzinCOC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C12173.5Standard non polar33892256
(R)-MeranzinCOC1=C(CC2OC2(C)C)C2=C(C=CC(=O)O2)C=C12255.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Meranzin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fdp-8490000000-04e17c594e4c443331432017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Meranzin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Meranzin 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 - (R)-Meranzin 10V, Positive-QTOFsplash10-03di-0090000000-ec2f14610581d133c66a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Positive-QTOFsplash10-0udi-5090000000-9814add42d4e72ab456e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Positive-QTOFsplash10-0079-1940000000-a23745f83dfd6d8172752016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Negative-QTOFsplash10-0a4i-1090000000-c98d2fb299f4b16639422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Negative-QTOFsplash10-056r-2890000000-5ce8f7cb7117f22853a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Negative-QTOFsplash10-00l7-9640000000-4e7acc3b4e57d93babdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Positive-QTOFsplash10-000i-0940000000-3f58cc96dd132eb95dcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Positive-QTOFsplash10-0f79-1790000000-c1bbe0507dcee5edb49a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Positive-QTOFsplash10-0udi-4980000000-e2988a7762a591c4fd112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 10V, Negative-QTOFsplash10-0a4i-0090000000-0647274cebfb179dc5a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 20V, Negative-QTOFsplash10-056r-1490000000-8fec533c8ebbc7ca97d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Meranzin 40V, Negative-QTOFsplash10-05o3-9560000000-3b216d03b9c037da1b7e2021-09-24Wishart 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 IDFDB021654
KNApSAcK IDNot Available
Chemspider ID3045741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3819217
PDB IDNot Available
ChEBI ID174412
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 glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular weight:
23355.625
Reactions
(R)-Meranzin → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[3-hydroxy-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbutan-2-yl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic aciddetails