Showing Compound Card for Aromadendrin (CDB005189)

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Record Information
Version1.0
Created at2020-04-17 19:18:16 UTC
Updated at2020-11-18 16:39:29 UTC
CannabisDB IDCDB005189
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Aromadendrin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-AromadendrinChEBI
(2R,3R)-DihydrokaempferolChEBI
DihydrokaempferolChEBI
(+)-DihydrokaempferolKegg
(+)-trans-3,4',5,7-TetrahydroxyflavanoneHMDB
(2R,3R)-2,3-dihydro-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
AromadendrolHMDB
KaturaninHMDB
AromadedrinMeSH, HMDB
dihydro-KaempferolMeSH, HMDB
dihydro-KempferolMeSH, HMDB
DihydrokempferolMeSH, HMDB
3,4',5,7-TetrahydroxyflavanonePhytoBank
3,4’,5,7-TetrahydroxyflavanonePhytoBank
(+)-(2R,3R)-DihydrokaempferolPhytoBank
(2R,3R)-3,4',5,7-TetrahydroxyflavanonePhytoBank
(2R,3R)-3,4’,5,7-TetrahydroxyflavanonePhytoBank
(2R,3R)-KaturaninPhytoBank
AromadendrinPhytoBank
AromadendrinePhytoBank
Chemical FormulaC15H12O6
Average Molecular Weight288.25
Monoisotopic Molecular Weight288.0634
IUPAC Name(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(+)-dihydrokaempferol
CAS Registry Number480-20-6
SMILES
O[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point247 - 249 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0030847
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002806
KNApSAcK IDC00007234
Chemspider ID109514
KEGG Compound IDC00974
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAromadendrin
METLIN IDNot Available
PubChem Compound122850
PDB IDNot Available
ChEBI ID15401
References
General ReferencesNot Available