Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:10:30 UTC
Primary IDFDB002423
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNepitrin
DescriptionNepitrin belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Nepitrin has been detected, but not quantified in, herbs and spices and rosemaries (Rosmarinus officinalis). This could make nepitrin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nepitrin.
CAS Number569-90-4
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1 g/LALOGPS
logP0.64ALOGPS
logP-0.023ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.55ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.5 m³·mol⁻¹ChemAxon
Polarizability46.06 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H22O12
IUPAC name2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C22H22O12/c1-31-21-14(33-22-20(30)19(29)17(27)15(7-23)34-22)6-13-16(18(21)28)11(26)5-12(32-13)8-2-3-9(24)10(25)4-8/h2-6,15,17,19-20,22-25,27-30H,7H2,1H3/t15-,17-,19+,20-,22-/m1/s1
InChI KeyDMXHXBGUNHLMQO-IWLDQSELSA-N
Isomeric SMILESCOC1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Average Molecular Weight478.4029
Monoisotopic Molecular Weight478.111126168
Classification
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 6-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNepitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-9303700000-f9574a35f849db5c12c7Spectrum
Predicted GC-MSNepitrin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-057i-3331019000-38b2cafd26dd84df6bc2Spectrum
Predicted GC-MSNepitrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0139800000-7381f32c2b8ee1a69f172016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0159100000-979d75d706753b47e3692016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktb-2497000000-991fd2ec43cf5a239cc82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-2305900000-999ea13afeedb13c8e402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2279300000-3724520d9cb4bc0f4b8b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bd-4192000000-8c921c243c884d46107c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0009400000-f9e020672b78a8b5d2f72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009100000-6d263fc476cff759693e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-d4d9bcf99cd318117dc62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-9b72f8c346f02232b7382021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0005900000-560bf2b0d639545ffeb42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0009100000-a0e7174b3d26a8851a402021-09-24View Spectrum
NMRNot Available
ChemSpider ID107783
ChEMBL IDCHEMBL517682
KEGG Compound IDNot Available
Pubchem Compound ID120742
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30548
CRC / DFC (Dictionary of Food Compounds) IDCLS09-N:CLS10-H
EAFUS IDNot Available
Dr. Duke ID6-METHOXY-LUTEOLIN-7-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00004400
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).