Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:11:54 UTC
Update date2018-01-23 19:41:21 UTC
Primary IDFDB015535
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChrysin
DescriptionChrysin is a naturally occurring flavone chemically extracted from the blue passion flower (Passiflora caerulea). Honeycomb also contains small amounts. It is also reported in Oroxylum indicum or Indian trumpetflower. [Wikipedia]. Chrysin is found in many foods, some of which are sour cherry, carrot, wild carrot, and sweet orange.
CAS Number480-40-0
Structure
Thumb
Synonyms
SynonymSource
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-2-phenyl-4H-benzo(b)pyran-4-oneChEBI
5,7-Dihydroxy-2-phenylchromen-4-oneChEBI
5,7-DihydroxyflavoneChEBI
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9ciHMDB
Chrysinic acidHMDB
Ois 3HMDB
ChrysineMeSH
5,7-Dihydroxy-flavoneMeSH
ChrysinHMDB
5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP3.44ALOGPS
logP3.01ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.93 m³·mol⁻¹ChemAxon
Polarizability25.73 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O4
IUPAC name5,7-dihydroxy-2-phenyl-4H-chromen-4-one
InChI IdentifierInChI=1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
InChI KeyRTIXKCRFFJGDFG-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1
Average Molecular Weight254.2375
Monoisotopic Molecular Weight254.057908808
Classification
Description belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.86%; H 3.96%; O 25.17%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data318 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-2839000000-d0964f24f611d1c14e95View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2839000000-d0964f24f611d1c14e95View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0619000000-53f48b2cf9bad74e8f65View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0690000000-b07283fbd904f2901dd6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00gi-4439000000-26a54787c8758b70201fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0020900000-2dbcc5b06309066d63b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-0udi-0290000000-bdd70471bc805c9009b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fr6-0900000000-eee4ea35750adc10ef1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0090000000-2f6b543a5679e285552aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 26V, Negativesplash10-0udi-0290000000-bdd70471bc805c9009b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fr6-0900000000-eee4ea35750adc10ef1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0udi-0490000000-554518d0a352f29f8093View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0zfr-0950000000-51b2794dec3e6f6eea6aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-9cc0f49937b1a8fa0b34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-66cd77f4bd910deb0103View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0290000000-10a8a1236031b97efe7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fr6-0920000000-19bbcaf4a2423b2cb49dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014m-0900000000-200355de722ac7f96ef7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-ac2af4316665e2509d89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190000000-8f5ac4706417c39a2d62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0gbc-0900000000-d619653decf40895a511View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0390000000-eb3159b6ffe6b7c816b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-006t-3930000000-3775c8b9ef4bbb0cb352View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-c8b5dd372a2667398b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c8a1f1ae722a2b79308aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-191437b0a57325aec07aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-4950000000-f1f4abaafec11c500890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-4c48fd26f99d65b20cd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-acfd169c302ecc539f58View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1940000000-98ef8f11854760675c83View in MoNA
ChemSpider ID4444926
ChEMBL IDCHEMBL117
KEGG Compound IDC10028
Pubchem Compound ID5281607
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID240
DrugBank IDNot Available
HMDB IDHMDB36619
CRC / DFC (Dictionary of Food Compounds) IDKDC55-C:KDC55-C
EAFUS IDNot Available
Dr. Duke IDCHRYSIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID57D
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChrysin
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 aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti bacillary33282 A substance that kills or slows the growth of bacteria.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti gout52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti multidrug resistanceDUKE
anti mutagenicDUKE
anti proliferantDUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti shigellic33282 A substance that kills or slows the growth of bacteria.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti thrombic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
apoptoticDUKE
aromatase inhibitor50790 An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
caspase-3 inhibitor37670 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).DUKE
caspase-9 inhibitor37670 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cytochrome-CYP1A1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
DNA-protectiveDUKE
estrogenicDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypotensiveDUKE
hypouricemicDUKE
ICAM-1 inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
JNK 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
monoamine-oxidase 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
mutagenicDUKE
myorelaxantDUKE
nitric-oxide-genicDUKE
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
radioprotective35232 Any pharmaceutical compound containing a radioisotope.DUKE
termitifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
testosterogenicDUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
vasorelaxantDUKE
VEGF inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).