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Aromadendrin (FDB002806)

Record Information
Version1.0
Creation date2010-04-08 22:05:32 UTC
Update date2020-09-17 15:41:00 UTC
Primary IDFDB002806
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAromadendrin
DescriptionAromadendrin, also known as dihydrokaempferol, belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Aromadendrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Aromadendrin has been detected, but not quantified in, several different foods, such as anises, sorrels, tamarinds, wax apples, and sea-buckthornberries. This could make aromadendrin a potential biomarker for the consumption of these foods. A tetrahydroxyflavanone having hydroxy groupa at the 3-, 4'-, 5- and 7-positions.
CAS Number480-20-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.23ALOGPS
logP2.12ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.63 m³·mol⁻¹ChemAxon
Polarizability28.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O6
IUPAC name(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H/t14-,15+/m0/s1
InChI KeyPADQINQHPQKXNL-LSDHHAIUSA-N
Isomeric SMILESO[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
Average Molecular Weight288.2522
Monoisotopic Molecular Weight288.063388116
Classification
Description Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative Parents
Substituents
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanonol
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 62.50%; H 4.20%; O 33.30%DFC
Melting PointMp 247-249°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +45 (c, 4 in 50% Me2CO aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAromadendrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-1980000000-7cc958a9df81a10ae014Spectrum
Predicted GC-MSAromadendrin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0imi-2640190000-17f316a7c4647990a2a1Spectrum
Predicted GC-MSAromadendrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAromadendrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-000i-0090000000-e14b8e1e7fc48a9342822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-000i-0190000000-caa95001f74424bb52222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-000l-0390000000-8b70a51c1d08add76cf32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0f6y-0960000000-b5c81668eb25d016bb9a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0zfs-0920000000-d3910e809932fbdc13352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0zfs-0910000000-e6f229665ff43b8145a02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-0pba-0900000000-c780a80ff30a1abeba782020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 26V, positivesplash10-0pb9-2900000000-c4b467ede4839437ed7e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 31V, positivesplash10-0aor-4900000000-c1e3fa3d2f2a0c2ba7642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 36V, positivesplash10-066r-7900000000-1c0136dd8c1655bec51c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 43V, positivesplash10-014i-9600000000-5763889d46e13d2844352020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 49V, positivesplash10-014i-9400000000-a998ccc5e9ebd751af382020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-0gb9-9200000000-07dde11b111d2476a2312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-0udi-0900000000-68e4c8151c0f883627d92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-014j-0790000000-7f8b28dbff78e274843d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-0002-0900000000-5f1aa642fd3aeaee0a732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-0006-0090000000-57c4f9f24ca1c1e7c2322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-0006-9000000000-59c49d4b3fd90c1740fd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 20V, positivesplash10-00di-0900000000-ffdcca5bd2b965040c672020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-4ceeaed3349641593d662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kg9-0960000000-b54d012869a01298fd892016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmr-4900000000-cb8757bc53bef9864fed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-72d51ba5728ad3048a1e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1960000000-7be39e33eed6781c50f62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a73-5910000000-a72844280b3dd1d0350e2016-08-03View Spectrum
NMRNot Available
ChemSpider ID642
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID662
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID122
DrugBank IDNot Available
HMDB IDHMDB30847
CRC / DFC (Dictionary of Food Compounds) IDHGW24-C:CNS53-K
EAFUS IDNot Available
Dr. Duke IDAROMADENDRIN
BIGG IDNot Available
KNApSAcK IDC00007234
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 septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.