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Record Information
Version1.0
Created at2021-06-22 17:28:51 UTC
Updated at2021-08-20 00:00:48 UTC
NP-MRD IDNP0043913
Secondary Accession NumbersNone
Natural Product Identification
Common NameKaempferide
DescriptionKaempferide belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferide is considered to be a flavonoid. Kaempferide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Kaempferide is found in Agnorhiza bolanderi, Agrimonia eupatoria, Alnus glutinosa, Alnus japonica, Alpinia conchigera, Alpinia galanga, Arnica parryi, Baccharis darwinii, Baccharis dracunculifolia, Balsamorhiza deltoidea, Butea monosperma, Catharanthus roseus, Centaurea deflexa, Chromolaena odorata, Cistus creticus, Cistus laurifolius, Cistus parviflorus, Cota altissima, Currania robertiana, Deinandra kelloggii, Dianthus caryophyllus, Ericameria laricifolia, Ageratina altissima, Grindelia tarapacana, Gymnocarpium robertianum, Hazardia squarrosa, Monticalia vaccinioides, Notholaena standleyi, Pentagramma triangularis, Phyllanthus virgatus, Populus alba, Populus tremula, Populus tremuloides and Tamarix nilotica. It was first documented in 2009 (PMID: 19571393). Based on a literature review a small amount of articles have been published on Kaempferide (PMID: 27719955) (PMID: 22993853) (PMID: 23123452) (PMID: 23208771).
Structure
Thumb
Synonyms
ValueSource
1.3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyroneChEBI
4'-O-MethylkaempferolChEBI
CampherideChEBI
Kaempferol 4'-methyl etherChEBI
KempferideKegg
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyroneHMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
3,5,7-Trihydroxy-4'-methoxy-flavoneHMDB
4'-Methoxy-3,5,7-trihydroxy-flavanoneHMDB
4'-Methoxy-3,5,7-trihydroxyflavoneHMDB
4'-MethylkaempferolHMDB
5,7-Dihydroxy-4'-methoxyflavonolHMDB
KaemferideHMDB
KaempferidHMDB
KampferideHMDB
KampherideHMDB
3 5 7-Trihydroxy-4'-methoxyflavoneHMDB
Chemical FormulaC16H12O6
Average Mass300.2629 Da
Monoisotopic Mass300.06339 Da
IUPAC Name3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Namekaempferide
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C16H12O6/c1-21-10-4-2-8(3-5-10)16-15(20)14(19)13-11(18)6-9(17)7-12(13)22-16/h2-7,17-18,20H,1H3
InChI KeySQFSKOYWJBQGKQ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agnorhiza bolanderiLOTUS Database
Agrimonia eupatoriaLOTUS Database
Alnus glutinosaLOTUS Database
Alnus japonicaLOTUS Database
Alpinia conchigeraLOTUS Database
Alpinia galangaLOTUS Database
Alpinia officinarumKNApSAcK Database
Arnica parryiLOTUS Database
Astragalus complanatusKNApSAcK Database
Baccharis darwiniiLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Baccharis pilularisKNApSAcK Database
Baccharis vimineaKNApSAcK Database
Balsamorhiza deltoideaLOTUS Database
Butea monospermaLOTUS Database
Calceolaria irazeunsisKNApSAcK Database
Capsella bursa-pastorisKNApSAcK Database
Catharanthus roseusLOTUS Database
Centaurea deflexaLOTUS Database
Chromolaena odorataLOTUS Database
Chrysothamnus nauseosusKNApSAcK Database
Cistus creticusLOTUS Database
Cistus laurifoliusLOTUS Database
Cistus parviflorusLOTUS Database
Citrus paradisiFooDB
Costus spicatusKNApSAcK Database
Cota altissimaLOTUS Database
Crocus sativusKNApSAcK Database
Currania robertiana-
Deinandra kelloggiiLOTUS Database
Dianthus caryophyllusLOTUS Database
Ericameria laricifoliaLOTUS Database
Eriodictyon sessilifoliumKNApSAcK Database
Eucryphia jinksiiKNApSAcK Database
Eupatorium rugosumLOTUS Database
Genista aetnensisKNApSAcK Database
Grindelia tarapacanaLOTUS Database
Gymnocarpium robertianumLOTUS Database
Hazardia squarrosaLOTUS Database
Kaempferia galangaKNApSAcK Database
Linaria dalmaticaKNApSAcK Database
Mirabilis viscosaKNApSAcK Database
Monticalia vaccinioidesLOTUS Database
Nothofagus menziesiiKNApSAcK Database
Nothofagus nervosaKNApSAcK Database
Notholaena standleyiLOTUS Database
Ozothamnus scutellifoliusKNApSAcK Database
Pentagramma triangularisLOTUS Database
Phyllanthus virgatusLOTUS Database
Populus albaLOTUS Database
Populus tremulaLOTUS Database
Populus tremuloidesLOTUS Database
Prunus cerasusFooDB
Prunus domesticaFooDB
Sedum sarmentosumKNApSAcK Database
Semecarpus vitiensisKNApSAcK Database
Syzygium aromaticumFooDB
Tamarix chinensisKNApSAcK Database
Tamarix niloticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 4p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point543.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility327.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.740 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.48ALOGPS
logP2.61ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.36 m³·mol⁻¹ChemAxon
Polarizability29.73 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037441
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016500
KNApSAcK IDC00001060
Chemspider ID4444985
KEGG Compound IDC10098
BioCyc IDCPD-7252
BiGG IDNot Available
Wikipedia LinkKaempferide
METLIN IDNot Available
PubChem Compound5281666
PDB IDNot Available
ChEBI ID6099
Good Scents IDrw1504521
References
General References
  1. Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
  2. Maruyama H, Sumitou Y, Sakamoto T, Araki Y, Hara H: Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats. Biol Pharm Bull. 2009 Jul;32(7):1244-50. doi: 10.1248/bpb.32.1244. [PubMed:19571393 ]
  3. Song P, Yao J, Ma HP, Ge BF, Chen KM, Guo XY, Lu X: [Comparison of effects of kaempferide and anhydroicaritin on biomineralization of cultured osteoblasts]. Yao Xue Xue Bao. 2012 Jul;47(7):890-6. [PubMed:22993853 ]
  4. Nawwar MA, Swilam NF, Hashim AN, Al-Abd AM, Abdel-Naim AB, Lindequist U: Cytotoxic isoferulic acidamide from Myricaria germanica (Tamaricaceae). Plant Signal Behav. 2013 Jan;8(1):e22642. doi: 10.4161/psb.22642. Epub 2012 Nov 3. [PubMed:23123452 ]
  5. Horibe I, Satoh Y, Shiota Y, Kumagai A, Horike N, Takemori H, Uesato S, Sugie S, Obata K, Kawahara H, Nagaoka Y: Induction of melanogenesis by 4'-O-methylated flavonoids in B16F10 melanoma cells. J Nat Med. 2013 Oct;67(4):705-10. doi: 10.1007/s11418-012-0727-y. Epub 2012 Dec 4. [PubMed:23208771 ]