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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:32 UTC
Update Date2022-03-07 02:52:35 UTC
HMDB IDHMDB0030544
Secondary Accession Numbers
  • HMDB30544
Metabolite Identification
Common NameGnaphaliin
DescriptionGnaphaliin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gnaphaliin is considered to be a flavonoid. Based on a literature review very few articles have been published on Gnaphaliin.
Structure
Data?1563862001
Synonyms
ValueSource
3-O-Methyl-8-methoxygalanginHMDB
5,7-Dihydroxy-3,8-dimethoxy-2-phenyl-4H-1-benzopyran-4-oneHMDB
5,7-Dihydroxy-3,8-dimethoxyflavoneHMDB
GnaphalinHMDB
Chemical FormulaC17H14O6
Average Molecular Weight314.2895
Monoisotopic Molecular Weight314.07903818
IUPAC Name5,7-dihydroxy-3,8-dimethoxy-2-phenyl-4H-chromen-4-one
Traditional Namegnaphaliin
CAS Registry Number33803-42-8
SMILES
COC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C17H14O6/c1-21-15-11(19)8-10(18)12-13(20)17(22-2)14(23-16(12)15)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3
InChI KeyOWQLBLNRUZULFV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point174 - 175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility83.41 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP3.24ALOGPS
logP2.72ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.97ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.11 m³·mol⁻¹ChemAxon
Polarizability31.22 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]+171.42731661259
DarkChem[M-H]-172.93431661259
DeepCCS[M+H]+173.43930932474
DeepCCS[M-H]-171.08130932474
DeepCCS[M-2H]-205.1630932474
DeepCCS[M+Na]+180.41630932474
AllCCS[M+H]+171.232859911
AllCCS[M+H-H2O]+167.632859911
AllCCS[M+NH4]+174.632859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-172.632859911
AllCCS[M+Na-2H]-171.932859911
AllCCS[M+HCOO]-171.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GnaphaliinCOC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C14338.3Standard polar33892256
GnaphaliinCOC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C12769.1Standard non polar33892256
GnaphaliinCOC1=C(O)C=C(O)C2=C1OC(=C(OC)C2=O)C1=CC=CC=C12712.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gnaphaliin,1TMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C)=CC(O)=C2C1=O2814.6Semi standard non polar33892256
Gnaphaliin,1TMS,isomer #2COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O)=CC(O[Si](C)(C)C)=C2C1=O2856.0Semi standard non polar33892256
Gnaphaliin,2TMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2C1=O2820.8Semi standard non polar33892256
Gnaphaliin,1TBDMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC(O)=C2C1=O3054.3Semi standard non polar33892256
Gnaphaliin,1TBDMS,isomer #2COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3078.2Semi standard non polar33892256
Gnaphaliin,2TBDMS,isomer #1COC1=C(C2=CC=CC=C2)OC2=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3238.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gnaphaliin GC-MS (Non-derivatized) - 70eV, Positivesplash10-08g1-0591000000-afe81f1e4f9ef00ee9902017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gnaphaliin GC-MS (2 TMS) - 70eV, Positivesplash10-006x-3336900000-f7eb0e85bd43b38151c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gnaphaliin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gnaphaliin , negative-QTOFsplash10-0002-0091000000-124a5e93428beae667de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gnaphaliin , positive-QTOFsplash10-0uxr-0019000000-9467bf5d8376c7f9f21e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gnaphaliin 6V, Positive-QTOFsplash10-014i-0129000000-30c3f0d40dcb17d955442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gnaphaliin 6V, Negative-QTOFsplash10-01ot-0195000000-b9072a2dbe6d9c7b60752021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 10V, Positive-QTOFsplash10-014i-0009000000-74366254c71683d86cac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 20V, Positive-QTOFsplash10-014i-0009000000-f7b7fce9470ede53b4a92016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 40V, Positive-QTOFsplash10-014i-2790000000-36ea33c39896b3ce66d12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 10V, Negative-QTOFsplash10-03di-0009000000-fd590dfdd66fe2b5e08d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 20V, Negative-QTOFsplash10-03di-0049000000-c02bf06f3fad2e3ab6f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 40V, Negative-QTOFsplash10-001i-1980000000-7c23df6d93ae35e0c7f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 10V, Positive-QTOFsplash10-014i-0009000000-2ba875095a8aafa31ef72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 20V, Positive-QTOFsplash10-014i-0009000000-cbffccd382907c719c4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 40V, Positive-QTOFsplash10-0159-1913000000-246263a900cde4f573b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 10V, Negative-QTOFsplash10-03di-0009000000-f92a1b64ae90a24db1582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 20V, Negative-QTOFsplash10-03di-0309000000-ca1a12c3d6e59212f3b52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gnaphaliin 40V, Negative-QTOFsplash10-02w9-4911000000-5bf43f16327e1bd1b2a42021-09-23Wishart 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 IDFDB002418
KNApSAcK IDC00004556
Chemspider ID8148502
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9972910
PDB IDNot Available
ChEBI ID656980
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1820881
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.. .