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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:47:36 UTC
Update Date2022-03-07 02:55:47 UTC
HMDB IDHMDB0038473
Secondary Accession Numbers
  • HMDB38473
Metabolite Identification
Common NameTorachrysone
DescriptionTorachrysone belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Torachrysone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make torachrysone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Torachrysone.
Structure
Data?1563863203
Synonyms
ValueSource
1-nitroso-1-Phenyl-ureaHMDB
2-Acetyl-1,8-dihydroxy-6-methoxy-3-methylnaphthaleneHMDB
N-nitroso-N-Phenyl-ureaHMDB
N-Phenyl-N-nitrosoureaHMDB
NakahaleneHMDB
NitrosophenylureaHMDB
Phenyl-nitroso-harnstoffHMDB
Urea, 1-nitroso-1-phenyl- (8ci)HMDB
Chemical FormulaC14H14O4
Average Molecular Weight246.2586
Monoisotopic Molecular Weight246.089208936
IUPAC Name1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethan-1-one
Traditional Name1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethanone
CAS Registry Number22649-04-3
SMILES
COC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C1
InChI Identifier
InChI=1S/C14H14O4/c1-7-4-9-5-10(18-3)6-11(16)13(9)14(17)12(7)8(2)15/h4-6,16-17H,1-3H3
InChI KeyBIJOPUWEMBBDEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 1-naphthol
  • Acetophenone
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Vinylogous acid
  • Ketone
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point214 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility144.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.71ALOGPS
logP2.92ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.3ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.38 m³·mol⁻¹ChemAxon
Polarizability25.8 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]+158.41231661259
DarkChem[M-H]-160.60131661259
DeepCCS[M+H]+159.13430932474
DeepCCS[M-H]-156.77630932474
DeepCCS[M-2H]-189.66230932474
DeepCCS[M+Na]+165.22730932474
AllCCS[M+H]+154.932859911
AllCCS[M+H-H2O]+151.032859911
AllCCS[M+NH4]+158.532859911
AllCCS[M+Na]+159.532859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-158.632859911
AllCCS[M+HCOO]-158.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TorachrysoneCOC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C13514.4Standard polar33892256
TorachrysoneCOC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C12210.1Standard non polar33892256
TorachrysoneCOC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C12352.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Torachrysone,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(O)=C(C(C)=O)C(C)=CC2=C12292.6Semi standard non polar33892256
Torachrysone,1TMS,isomer #2COC1=CC(O)=C2C(O[Si](C)(C)C)=C(C(C)=O)C(C)=CC2=C12245.2Semi standard non polar33892256
Torachrysone,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=C(C(C)=O)C(C)=CC2=C12294.3Semi standard non polar33892256
Torachrysone,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O)=C(C(C)=O)C(C)=CC2=C12521.2Semi standard non polar33892256
Torachrysone,1TBDMS,isomer #2COC1=CC(O)=C2C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(C)=CC2=C12486.7Semi standard non polar33892256
Torachrysone,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(C)=CC2=C12740.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Torachrysone GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1290000000-cc6d5507e5ef3cc44ebe2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Torachrysone GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-3019000000-f6b04c5681ef956527452017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Torachrysone 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 - Torachrysone 10V, Positive-QTOFsplash10-0002-0090000000-38e6500d2b0161c2695d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 20V, Positive-QTOFsplash10-0002-0090000000-b69e0a7f88e6278aeff62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 40V, Positive-QTOFsplash10-0002-2950000000-8f1383df87601c2a2b832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 10V, Negative-QTOFsplash10-0002-0090000000-83a949d132fc002a3d9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 20V, Negative-QTOFsplash10-0002-0090000000-0d630fd9238182ff4ed12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 40V, Negative-QTOFsplash10-0fka-2950000000-afc055777a0868e846792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 10V, Negative-QTOFsplash10-0002-0090000000-f3df51ecec20c65b25b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 20V, Negative-QTOFsplash10-0f6t-0090000000-998da1a0209fcb1972582021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 40V, Negative-QTOFsplash10-03dj-1910000000-ecc17d89c6faf2444a0d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 10V, Positive-QTOFsplash10-0002-0090000000-30fbf0a5a6d5a52e1a952021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 20V, Positive-QTOFsplash10-004j-0090000000-d3441a5332d9bec8bd7c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Torachrysone 40V, Positive-QTOFsplash10-08i9-4920000000-a1bb758ff61860b6779b2021-09-25Wishart 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 IDFDB017837
KNApSAcK IDC00037918
Chemspider ID4479579
KEGG Compound IDC17672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321977
PDB IDNot Available
ChEBI ID81265
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1868611
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.. .