NP-MRD: Showing NP-Card for (2R,3R)-dihydrokaempferol (NP0331442)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2023-01-14 16:06:28 UTC

Updated at

2024-04-19 09:41:17 UTC

NP-MRD ID

NP0331442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R,3R)-dihydrokaempferol

Description

Aromadendrin, 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.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.3313   -2.3967   -2.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -1.6749   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8696   -0.7473   -0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0280   -0.3601   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270   -0.8767   -2.4541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8975    0.5214   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460    1.0083    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4556    1.9012    1.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791    0.6280    1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415   -0.2540    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772   -0.6591    1.2230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019   -1.2811    0.6044 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8127   -0.2876    0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0955   -0.6451    0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790    0.3140    0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183    1.6074    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348    2.5615    0.2477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155    1.9218    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5060    0.9897    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -1.8032   -0.7644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7780   -3.1735   -0.8358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1437   -0.6555   -2.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8054    0.8187   -1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3142    2.8805    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    1.0425    2.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0163   -2.1336    1.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3109   -1.6715    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0900    0.0283    1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473    3.1318    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935    2.9237   -0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958    1.2822   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863   -1.3146   -1.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2075   -3.6265   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  2 20  1  0
 19 13  1  0
  3 10  1  0
 21 33  1  0
 20 32  1  6
 12 26  1  1
  9 25  1  0
  8 24  1  0
  6 23  1  0
  5 22  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv1652309272007402D          

 21 23  0  0  0  0            999 V2000
 9999.6516 9998.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0779 9998.9926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.222310001.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2265 9998.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.797610000.6492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.226610000.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.512010000.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5120 9999.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2265 9998.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.652310000.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.937810000.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9378 9999.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6523 9998.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3668 9999.4071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.366810000.2322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.507910001.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.793410001.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.078910001.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.078810000.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.793310000.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.507910000.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7  5  1  0  0  0  0
  9  4  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
  1 13  2  0  0  0  0
 14  2  1  1  0  0  0
 11  6  2  0  0  0  0
  9 12  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
 15 19  1  6  0  0  0
 16  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331442

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
PADQINQHPQKXNL-LSDHHAIUSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.058267823721767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
2.1199495896666667

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.133303712906603

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.749666077541202

> <JCHEM_PKA_STRONGEST_BASIC>
-4.035510007878767

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
72.628

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-dihydrokaempferol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0168663.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6798664.786   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8672.6828670.188   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.3568663.239   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8660.6898667.879   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.3568667.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.0228667.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0228665.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3568664.790   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8666.0188667.870   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8664.6848667.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6848665.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.0188664.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3518665.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3518667.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8671.3488669.418   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8670.0148670.188   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.6818669.418   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6808667.878   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.0148667.108   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.3488667.878   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   16                                                            
CONECT    4    9                                                            
CONECT    5    7                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8    5                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   12                                                  
CONECT   10   11   15                                                       
CONECT   11   12   10    6                                                  
CONECT   12   11   13    9                                                  
CONECT   13   12   14    1                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   10   19                                                  
CONECT   16   17   21    3                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   15                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(+)-Aromadendrin	ChEBI
(2R,3R)-Dihydrokaempferol	ChEBI
Dihydrokaempferol	ChEBI
(+)-Dihydrokaempferol	Kegg
(+)-trans-3,4',5,7-Tetrahydroxyflavanone	HMDB
(2R,3R)-2,3-dihydro-3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	HMDB
Aromadendrol	HMDB
Katuranin	HMDB
Aromadedrin	MeSH, HMDB
dihydro-Kaempferol	MeSH, HMDB
dihydro-Kempferol	MeSH, HMDB
Dihydrokempferol	MeSH, HMDB
3,4',5,7-Tetrahydroxyflavanone	PhytoBank
3,4’,5,7-Tetrahydroxyflavanone	PhytoBank
(+)-(2R,3R)-Dihydrokaempferol	PhytoBank
(2R,3R)-3,4',5,7-Tetrahydroxyflavanone	PhytoBank
(2R,3R)-3,4’,5,7-Tetrahydroxyflavanone	PhytoBank
(2R,3R)-Katuranin	PhytoBank
Aromadendrin	PhytoBank
Aromadendrine	PhytoBank

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2522 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

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

Traditional Name

(+)-dihydrokaempferol

CAS Registry Number

Not Available

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 Key

PADQINQHPQKXNL-LSDHHAIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.79 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500.2 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavanone (CHEBI:15401 )
dihydroflavonols (CHEBI:15401 )
Dihyroflavonols (C00974 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.23	ALOGPS
logP	2.12	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.63 m³·mol⁻¹	ChemAxon
Polarizability	28.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon