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Showing NP-Card for Dihydrokaempferol (NP0333951)

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Record Information
Version2.0
Created at2024-09-09 21:24:07 UTC
Updated at2024-09-09 21:24:08 UTC
NP-MRD IDNP0333951
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydrokaempferol
DescriptionDihydrokaempferol, also known as aromadendrin, is a member of the class of 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. Dihydrokaempferol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Dihydrokaempferol can be found in european plum and tea, which makes dihydrokaempferol a potential biomarker for the consumption of these food products. Aromadendrin (aromodedrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of Pinus sibirica.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333951 (Dihydrokaempferol)


  Mrv2104 05242323562D          

 21 23  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  7  2  0  0  0  0
  2  4  2  0  0  0  0
  2  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  2  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 12  2  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  2  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
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3D MOL for NP0333951 (Dihydrokaempferol)

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3D SDF for NP0333951 (Dihydrokaempferol)

  Mrv2104 05242323562D          

 21 23  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  7  2  0  0  0  0
  2  4  2  0  0  0  0
  2  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  2  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  9 17  1  0  0  0  0
 10 12  2  0  0  0  0
 10 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 19  2  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1/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

> <INCHI_KEY>
PADQINQHPQKXNL-UHFFFAOYNA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.053559183921227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
2.1199495896666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.133303938902685

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.749666109476664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.035510007878767

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
72.62800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
aromadendrin

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333951 (Dihydrokaempferol)
Download
PDB for NP0333951 (Dihydrokaempferol)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    9   10                                                       
CONECT    6    9   11                                                       
CONECT    7    1    2   15                                                  
CONECT    8    3    4   16                                                  
CONECT    9    5    6   17                                                  
CONECT   10    5   12   18                                                  
CONECT   11    6   12   21                                                  
CONECT   12   10   11   13                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   20                                                  
CONECT   15    7   14   21                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

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3D PDB for NP0333951 (Dihydrokaempferol)
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SMILES for NP0333951 (Dihydrokaempferol)
OC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
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INCHI for NP0333951 (Dihydrokaempferol)
InChI=1/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
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H12O6
Average Mass288.2550 Da
Monoisotopic Mass288.06339 Da
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namearomadendrin
CAS Registry NumberNot Available
SMILES
OC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1/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
InChI KeyPADQINQHPQKXNL-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavanonols. These 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 DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.12ChemAxon
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
Polarizability28.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAromadendrin  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Choudhary N, Pucker B: Conserved amino acid residues and gene expression patterns associated with the substrate preferences of the competing enzymes FLS and DFR. PLoS One. 2024 Aug 28;19(8):e0305837. doi: 10.1371/journal.pone.0305837.  eCollection 2024. [PubMed:39196921  ] 
  2. Zhu S, Cui M, Zhao Q: Characterization of the 2ODD genes of DOXC subfamily and its members involved in flavonoids biosynthesis in Scutellaria baicalensis. BMC Plant Biol. 2024 Aug 26;24(1):804. doi: 10.1186/s12870-024-05519-1. [PubMed:39183318  ] 
  3. Ding Y, Shen J, Li H, Sun Y, Jiang T, Kong X, Han R, Zhao C, Zhang X, Zhao X: Physiological and molecular mechanism of Populus pseudo-cathayana x Populus deltoides response to Hyphantria cunea. Pestic Biochem Physiol. 2024 Jun;202:105969. doi: 10.1016/j.pestbp.2024.105969.  Epub 2024 May 26. [PubMed:38879313  ] 
  4. Chen Q, Song D, Sun X, Tian Y, Yan Z, Min T, Wang H, Wang L: Functional Characterization of F3H Gene and Optimization of Dihydrokaempferol Biosynthesis in Saccharomyces cerevisiae. Molecules. 2024 May 8;29(10):2196. doi: 10.3390/molecules29102196. [PubMed:38792058  ] 
  5. Shahzadi Z, Yousaf Z, Anjum I, Bilal M, Yasin H, Aftab A, Booker A, Ullah R, Bari A: Network pharmacology and molecular docking: combined computational approaches to explore the antihypertensive potential of Fabaceae species. Bioresour Bioprocess. 2024 May 20;11(1):53. doi: 10.1186/s40643-024-00764-6. [PubMed:38767701  ] 
  6. Zhang L, Zengin G, Ozfidan-Konakci C, Yildiztugay E, Arikan B, Ekim R, Koyukan B, Elbasan F, Lucini L: Exogenous curcumin mitigates As stress in spinach plants: A biochemical and metabolomics investigation. Plant Physiol Biochem. 2024 Jun;211:108713. doi: 10.1016/j.plaphy.2024.108713.  Epub 2024 May 8. [PubMed:38739963  ] 
  7. Zhang X, Wu D, Zhang L, Zhang H, Yang L, Wei L, Mei H, Luo L, Jiang Z, Huang C: Predicting the potential mechanism of radix chimonanthi pracecocis in treating osteoarthritis by network pharmacology analysis combined with experimental validation. J Ethnopharmacol. 2024 Sep 15;331:118231. doi: 10.1016/j.jep.2024.118231. Epub  2024 May 6. [PubMed:38718891  ] 
  8. Medini F, Ksouri R, Msaada K, Legault J: Phenolic compounds from Limonium densiflorum: a multifaceted approach to antioxidant, anti-inflammatory, anticancer, and anti-influenza activities. Int J Environ Health Res. 2024 Apr 24:1-11. doi: 10.1080/09603123.2024.2342572. [PubMed:38656221  ] 
  9. Zhang X, Geng A, Cao D, Dugarjaviin M: Identification of mulberry leaf flavonoids and evaluating their protective effects on H(2)O(2)-induced oxidative damage in equine skeletal muscle satellite cells. Front Mol Biosci. 2024 Apr 8;11:1353387. doi: 10.3389/fmolb.2024.1353387.  eCollection 2024. [PubMed:38650596  ] 
  10. Jian JZ, Lang TQ, Zhang W, Feng YQ, Luo GY: [A new nor-neolignan compound identified from Itea yunnanensis]. Zhongguo Zhong Yao Za Zhi. 2024 Mar;49(6):1564-1569. doi:  10.19540/j.cnki.cjcmm.20231208.201. [PubMed:38621940  ]