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Showing Compound Biflorin (FDB001390)

Record Information
Version1.0
Creation date2010-04-08 22:04:57 UTC
Update date2019-11-26 02:56:26 UTC
Primary IDFDB001390
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBiflorin
DescriptionConstituent of Eugenia caryophyllata (clove) Biflorin is an o-naphthoquinone isolated from Capraria biflora L. (Scrophulariaceae, a perennial shrub widely distributed in several countries of tropical America). Biflorin has cytotoxic and antioxidant potential, strongly inhibiting the growth of five tested tumor cell lines, especially the skin, breast and colon cancer cells with IC50 of 0.40, 0.43 and 0.88 micro/ml for B16, MCF-7 and HCT-8, respectively, while the antioxidant activity was assayed against autoxidation of oleic acid in a water/alcohol system. (PMID: 16042338). Biflorin is found in herbs and spices and cloves.
CAS Number89701-85-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
6-b-D-Glucopyranosyl-5,7-dihydroxy-2-methyl-4H-1-benzopyran-4-one, 9CIdb_source
6beta-C-Glucopyranosyl-5,7-dihydroxy-2-methylchromonebiospider
Predicted Properties
PropertyValueSource
Water Solubility13.1 g/LALOGPS
logP-0.72ALOGPS
logP-0.84ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)6.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity84.19 m³·mol⁻¹ChemAxon
Polarizability33.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H18O9
IUPAC name5,7-dihydroxy-2-methyl-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H18O9/c1-5-2-6(18)10-8(24-5)3-7(19)11(13(10)21)16-15(23)14(22)12(20)9(4-17)25-16/h2-3,9,12,14-17,19-23H,4H2,1H3
InChI KeyXTZWWMZDVUKEDJ-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)C2=C(O1)C=C(O)C(C1OC(CO)C(O)C(O)C1O)=C2O
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
Classification
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.24%; H 5.12%; O 40.64%DFC
Melting PointMp 300-303° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]28D +24.4 (c, 0.34 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0009000000-1a02b48834390ce8c6fd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-2329000000-ebc76c4a88ef0fd2305f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lfu-4391000000-cd8add8440ed63e251292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0119000000-25b771ff671cbb7d2a262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdx-8598000000-1163327bad8734380b1b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9660000000-28a9f069e391f5cf52082016-08-03View Spectrum
NMRNot Available
ChemSpider ID390528
ChEMBL IDCHEMBL463312
KEGG Compound IDC08996
Pubchem Compound ID441959
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02336
CRC / DFC (Dictionary of Food Compounds) IDBZW64-D:BZW64-D
EAFUS IDNot Available
Dr. Duke IDBIFLORIN
BIGG IDNot Available
KNApSAcK IDC00002417
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti gingivitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti periodonticDUKE
anti plaqueDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
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).