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Showing Compound Meloside (FDB005272)

Record Information
Version1.0
Creation date2010-04-08 22:06:36 UTC
Update date2019-11-26 03:00:27 UTC
Primary IDFDB005272
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMeloside
DescriptionMeloside, also known as isovitexin 2''-beta-D-O-glucoside or 2'-O-beta-D-glucosylisovitexin, is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Meloside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Meloside can be found in muskmelon, which makes meloside a potential biomarker for the consumption of this food product.
CAS Number60767-80-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility6.26 g/LALOGPS
logP-0.67ALOGPS
logP-1.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area256.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.45 m³·mol⁻¹ChemAxon
Polarizability56.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O15
IUPAC name6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25+,26-,27+/m1/s1
InChI KeyRQTTXGQDIROLTQ-FASGCTRLSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
Classification
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl 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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00o1-0100980000-7b111821dedaef51478e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0100910000-b5cf2d8afe8420b67a4c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2597610000-0383fb45f9177024e5bb2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-1110590000-e4d05a8e9819ea8da0f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01sl-4713940000-07722737d0a58965f1f32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03gl-5926300000-58fa5addcce7f7ed91272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-54e89fd530db4e77b6eb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000090000-54e89fd530db4e77b6eb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0400980000-c6c96f609f5462c4a2b22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-c2b3948e01c1f6089ea82021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000090000-888637a47809c9cf248e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0900530000-39fd5e23f8dd6ec787432021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDMELOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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
MuskmelonExpected but not quantifiedNot AvailableDUKE
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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).