NP-MRD: Showing NP-Card for (2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one (NP0044212)

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Record Information

Version

1.0

Created at

2021-12-17 00:29:35 UTC

Updated at

2022-08-31 20:04:56 UTC

NP-MRD ID

NP0044212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

Description

5,7-Dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one, also known as naringenin-7-sulfate or 4',5,7-trihydroxyflavanone, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. 5,7-Dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one has been detected, but not quantified in, tea. This could make 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one a potential biomarker for the consumption of these foods. (2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one is found in Acer pictum, Achyrocline flaccida, Acritopappus confertus, Adenothamnus validus, Aeonium lindleyi, Afzelia bipindensis, Aglaia rubiginosa, Allagopappus viscosissimus, Alpinia zerumbet, Anastatica hierochuntica, Anethum graveolens, Antiphiona pinnatisecta, Artemisia argyi, Artemisia barrelieri, Artemisia campestris, Artemisia dracunculus, Aster koraiensis, Baccharis dracunculifolia, Baccharis retusa, Bahiopsis laciniata, Berchemia formosana, Berchemia racemosa, Betula maximowicziana, Betula pubescens, Brosimum acutifolium, Broussonetia papyrifera, Brucea javanica, Cadophora gregata, Camellia sinensis, Carapa guianensis, Carduus tenuiflorus, Cedrus deodara, Centaurea cyanus, Centaurea pallescens, Chrysanthemum morifolium, Chrysothamnus viscidiflorus, Cicer arietinum, Cistus laurifolius, Citrus aurantium, Citrus limon, Citrus medica, Citrus trifoliata, Combretum imberbe, Commiphora wightii, Coriaria intermedia, Corymbia maculata, Cota palaestina, Cotoneaster orbicularis, Couepia paraensis, Craspedolobium schochii, Crocus sativus, Crotalaria assamica, Cryptomeria japonica, Cycas circinalis, Dalbergia parviflora, Deinandra lobbii, Dendrobium densiflorum, Diplostephium cinereum, Dracocephalum tanguticum, Elaeodendron croceum, Entada phaseoloides, Equisetum arvense, Eriodictyon angustifolium, Euchresta japonica, Ficus nervosa, Ficus pumila, Flemingia philippinensis, Garcinia multiflora, Glycine max, Glycyrrhiza echinata, Glycyrrhiza glabra, Glycyrrhiza uralensis, Goyazianthus tetrastichus, Gynerium sagittatum, Helichrysum arenarium, Helichrysum armenium, Heliotropium chenopodiaceum, Heliotropium sclerocarpum, Heliotropium sinuatum, Heliotropium taltalense, Inula salsoloides, Inulanthera dregeana, Juniperus chinensis, Laguncularia racemosa, Lamyropsis cynaroides, Leiocarpa semicalva, Lespedeza cyrtobotrya, Limonium aureum, Limonium sinense, Lippia graveolens, Lippia origanoides, Lotus uliginosus, Lychnophora ericoides, Maackia amurensis, Maclura cochinchinensis, Maclura pomifera, Maclura tricuspidata, Mandevilla hirsuta, Matricaria chamomilla, Matthiola incana, Medicago truncatula, Micromeria graeca, Millettia brandisiana, Mimosa tenuiflora, Monopteryx inpae, Nymphaea guineensis, Origanum dictamnus, Ormosia henryi, Ormosia monosperma, Paulownia coreana, Paulownia tomentosa, Phlomis floccosa, Phyllanthus emblica, Picea jezoensis, Piper crassinervium, Pittocaulon praecox, Pittocaulon velatum, Plazia daphnoides, Podocarpus fasciculus, Populus balsamifera, Populus davidiana, Populus deltoides, Populus szechuanica, Populus tremula, Premna fulva, Prunus avium, Prunus campanulata, Prunus cerasus, Prunus cornuta, Prunus davidiana, Prunus domestica, Prunus mume, Prunus persica, Prunus serrulata, Prunus verecunda, Prunus yedoensis, Pyracantha coccinea, Retama raetam, Rhynchosia beddomei, Salix caprea, Salvia mexicana, Salvia officinalis, Salvia rosmarinus, Salvia xalapensis, Sarcophyte sanguinea, Satureja cuneifolia, Scalesia baurii, Senna obtusifolia, Sinningia cardinalis, Smilax bracteata, Smilax corbularia, Smilax excelsa, Solanum lycopersicum, Sorghum bicolor, Stachys aegyptiaca, Steiractinia sodiroi, Streptomyces halstedii, Swartzia polyphylla, Syzygium jambos, Taxus wallichiana, Teucrium chamaedrys, Thymus herba-barona, Thymus vulgaris, Urospermum dalechampii, Vachellia nilotica, Viburnum cotinifolium, Vigna angularis, Viscum coloratum, Vitis vinifera, Wyethia angustifolia, Xanthoceras sorbifolium, Xanthorrhoea glauca and Xerochrysum bracteatum. A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4'.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.4135    2.7839   -1.3725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603    1.8154   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791    1.5074   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5243    0.1147   -0.6037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9200   -0.2523   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550   -0.6728    1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5693   -1.0072    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5850   -0.9365    0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9000   -1.2736    0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -0.5154   -0.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9371   -0.1822   -1.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121   -0.8082   -0.1262 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7514   -0.4689   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7194   -1.4240    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472   -1.0761    0.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9945   -2.0523    0.5721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827    0.1851    0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277    1.1664   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9557    2.4404   -0.5466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2061    0.8349   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    1.3919    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    2.2223   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.1874   -1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812   -0.7398    1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -1.3392    2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5682   -0.5989    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -0.4560   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6777    0.1470   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -2.4414    0.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2263   -2.1730    1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292    0.4134    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016    3.2073   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 11  1  0
 11 10  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 10  8  1  0
 12  4  1  0
 13 20  1  0
  9 26  1  0
  7 25  1  0
  6 24  1  0
 11 28  1  0
 10 27  1  0
  4 23  1  6
  3 21  1  0
  3 22  1  0
 19 32  1  0
 17 31  1  0
 16 30  1  0
 14 29  1  0
M  END


  Mrv1652304271814002D          

 20 22  0  0  0  0            999 V2000
    5.0012    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2

> <INCHI_KEY>
FTVWIRXFELQLPI-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.256

> <EXACT_MASS>
272.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
27.314576908172157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.835108050333333

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.199181425928916

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.856155974915031

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950228081125502

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
71.28980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asahina

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-18         0                                  
HETATM    1  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    5   15   18                                                  
CONECT   12    7   15   19                                                  
CONECT   13    7    8   20                                                  
CONECT   14    6   15   20                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Naringenin-7-sulfate	HMDB
4',5,7-Trihydroxyflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2560 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

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

Traditional Name

asahina

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2

InChI Key

FTVWIRXFELQLPI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, simulated)	Jtkp6n	Sumner Lab, University of Missouri	Jay Koller	2022-08-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Jtkp6n	Sumner Lab, University of Missouri	Jay Koller	2022-08-31	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acer pictum subsp. Mono	LOTUS Database	35616633
Achyrocline flaccida	LOTUS Database	35616633
Acritopappus confertus	LOTUS Database	35616633
Adenothamnus validus	LOTUS Database	35616633
Aeonium lindleyi	LOTUS Database	35616633
Afzelia bipindensis	LOTUS Database	35616633
Aglaia rubiginosa	LOTUS Database	35616633
Allagopappus viscosissimus	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Anastatica hierochuntica	LOTUS Database	35616633
Anethum graveolens	LOTUS Database	35616633
Antiphiona pinnatisecta	LOTUS Database	35616633
Artemisia argyi	LOTUS Database	35616633
Artemisia barrelieri	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Artemisia dracunculus	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis retusa	LOTUS Database	35616633
Bahiopsis laciniata	LOTUS Database	35616633
Berchemia formosana	LOTUS Database	35616633
Berchemia racemosa	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Brosimum acutifolium	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Cadophora gregata	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Carapa guianensis	LOTUS Database	35616633
Carduus tenuiflorus	LOTUS Database	35616633
Cedrus deodara	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea pallescens	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysothamnus viscidiflorus	LOTUS Database	35616633
Cicer arietinum	LOTUS Database	35616633
Cistus laurifolius	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus limon	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Combretum imberbe	LOTUS Database	35616633
Commiphora wightii	LOTUS Database	35616633
Coriaria intermedia	LOTUS Database	35616633
Corymbia maculata	LOTUS Database	35616633
Cota palaestina	LOTUS Database	35616633
Cotoneaster orbicularis	LOTUS Database	35616633
Couepia paraensis	LOTUS Database	35616633
Craspedolobium schochii	LOTUS Database	35616633
Crocus sativus	LOTUS Database	35616633
Crotalaria assamica	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Deinandra lobbii	LOTUS Database	35616633
Dendrobium densiflorum	LOTUS Database	35616633
Diplostephium cinereum	LOTUS Database	35616633
Dracocephalum tanguticum	LOTUS Database	35616633
Elaeodendron croceum	LOTUS Database	35616633
Entada phaseoloides	LOTUS Database	35616633
Equisetum arvense	LOTUS Database	35616633
Eriodictyon angustifolium	LOTUS Database	35616633
Euchresta japonica	LOTUS Database	35616633
Ficus nervosa	LOTUS Database	35616633
Ficus pumila	LOTUS Database	35616633
Flemingia philippinensis	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Glycyrrhiza echinata	LOTUS Database	35616633
Glycyrrhiza glabra	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Goyazianthus tetrastichus	LOTUS Database	35616633
Gynerium sagittatum	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Helichrysum armenium	LOTUS Database	35616633
Heliotropium chenopodiaceum	LOTUS Database	35616633
Heliotropium sclerocarpum	LOTUS Database	35616633
Heliotropium sinuatum	LOTUS Database	35616633
Heliotropium taltalense	LOTUS Database	35616633
Inula salsoloides	LOTUS Database	35616633
Inulanthera dregeana	LOTUS Database	35616633
Juniperus chinensis	LOTUS Database	35616633
Laguncularia racemosa	LOTUS Database	35616633
Lamyropsis cynaroides	LOTUS Database	35616633
Leiocarpa semicalva	LOTUS Database	35616633
Lespedeza cyrtobotrya	LOTUS Database	35616633
Limonium aureum	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Lippia graveolens	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Lotus uliginosus	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maclura cochinchinensis	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Maclura tricuspidata	LOTUS Database	35616633
Mandevilla hirsuta	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Matthiola incana	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Micromeria graeca	LOTUS Database	35616633
Millettia brandisiana	LOTUS Database	35616633
Mimosa tenuiflora	LOTUS Database	35616633
Monopteryx inpae	LOTUS Database	35616633
Nymphaea guineensis	LOTUS Database	35616633
Origanum dictamnus	LOTUS Database	35616633
Ormosia henryi	LOTUS Database	35616633
Ormosia monosperma	LOTUS Database	35616633
Paulownia coreana	LOTUS Database	35616633
Paulownia tomentosa	LOTUS Database	35616633
Phlomis floccosa	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Piper crassinervium	LOTUS Database	35616633
Pittocaulon praecox	LOTUS Database	35616633
Pittocaulon velatum	LOTUS Database	35616633
Plazia daphnoides	LOTUS Database	35616633
Podocarpus fasciculus	LOTUS Database	35616633
Populus balsamifera	LOTUS Database	35616633
Populus davidiana	LOTUS Database	35616633
Populus deltoides	LOTUS Database	35616633
Populus szechuanica	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Premna fulva	LOTUS Database	35616633
Prunus avium	LOTUS Database	35616633
Prunus campanulata	LOTUS Database	35616633
Prunus cerasus	LOTUS Database	35616633
Prunus cornuta	LOTUS Database	35616633
Prunus davidiana	LOTUS Database	35616633
Prunus domestica	LOTUS Database	35616633
Prunus mume	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Prunus serrulata	LOTUS Database	35616633
Prunus verecunda	LOTUS Database	35616633
Prunus yedoensis	LOTUS Database	35616633
Pyracantha coccinea	LOTUS Database	35616633
Retama raetam	LOTUS Database	35616633
Rhynchosia beddomei	LOTUS Database	35616633
Salix caprea	LOTUS Database	35616633
Salvia mexicana	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Salvia rosmarinus	LOTUS Database	35616633
Salvia xalapensis	LOTUS Database	35616633
Sarcophyte sanguinea	LOTUS Database	35616633
Satureja cuneifolia	LOTUS Database	35616633
Scalesia baurii	LOTUS Database	35616633
Senna obtusifolia	LOTUS Database	35616633
Sinningia cardinalis	LOTUS Database	35616633
Smilax bracteata	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Smilax excelsa	LOTUS Database	35616633
Solanum lycopersicum	LOTUS Database	35616633
Sorghum bicolor	LOTUS Database	35616633
Stachys aegyptiaca	LOTUS Database	35616633
Steiractinia sodiroi	LOTUS Database	35616633
Streptomyces halstedii	LOTUS Database	35616633
Swartzia polyphylla	LOTUS Database	35616633
Syzygium jambos	LOTUS Database	35616633
Taxus wallichiana	LOTUS Database	35616633
Teucrium chamaedrys	LOTUS Database	35616633
Thymus herba-barona	LOTUS Database	35616633
Thymus vulgaris	LOTUS Database	35616633
Urospermum dalechampii	LOTUS Database	35616633
Vachellia nilotica	LOTUS Database	35616633
Viburnum cotinifolium	LOTUS Database	35616633
Vigna angularis	LOTUS Database	35616633
Viscum coloratum	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wyethia angustifolia	LOTUS Database	35616633
Xanthoceras sorbifolium	LOTUS Database	35616633
Xanthorrhoea glauca	LOTUS Database	35616633
Xerochrysum bracteatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

Flavanone
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
Chromane
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavanone (CHEBI:50202 )

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	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.31 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

External Links

HMDB ID

HMDB0128074

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016687

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Naringenin

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

932

PDB ID

Not Available

ChEBI ID

50202

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one (NP0044212)

MOL for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

3D MOL for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

3D SDF for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

3D-SDF for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

PDB for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

3D PDB for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

SMILES for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

INCHI for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

Structure for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)

3D Structure for NP0044212 ((2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one)