NP-MRD: Showing NP-Card for 7-Hydroxyflavanone (NP0055474)

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Record Information

Version

2.0

Created at

2022-04-28 01:30:48 UTC

Updated at

2022-04-28 01:30:48 UTC

NP-MRD ID

NP0055474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Hydroxyflavanone

Description

(2S)-7-hydroxyflavanone belongs to the class of organic compounds known as flavanones. 7-Hydroxyflavanone is found in Ceratiola ericoides, Crinum asiaticum, Cryptocarya chinensis, Dalbergia cochinchinensis, Dalbergia sissoo, Diplotropis purpurea, Dracaena cinnabari, Flourensia heterolepis, Muntingia calabura, Oxytropis falcata, Phyllanthus sellowianus, Platymiscium praecox, Pterocarpus marsupium , Vachellia vernicosa, Vatairea heteroptera, Virgilia oroboides, Virola surinamensis and Zuccagnia punctata. 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 (2S)-7-hydroxyflavanone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.2152   -0.9028    2.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -0.0384    1.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    1.1549    1.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667    1.3472    0.1870 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8553    0.5617   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092    1.1219   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2015    0.3617   -0.7573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0790   -0.9820   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8260   -1.5398   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -0.7877   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.0931   -0.5953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5799    0.3936   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    0.2698   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7763   -0.4339   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8849   -0.5733   -1.4093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -1.0246    0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7328   -0.8941    1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -0.1880    1.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177    2.0446    2.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4092    1.0002    2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741    2.4537    0.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2356    2.1766   -0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1920    0.7967   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9457   -1.5701   -1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174   -2.5868   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463   -1.2130   -0.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6301    0.7356   -2.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6257    0.1221   -1.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966   -1.5669    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7052   -1.3319    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 10  5  1  0
 12 18  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  1
 13 27  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
M  END


  Mrv0541 02231217342D          

 18 20  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    1.4289   -1.6500    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 12  1  0  0  0  0
  9 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-8,14,16H,9H2/t14-/m0/s1

> <INCHI_KEY>
SWAJPHCXKPCPQZ-AWEZNQCLSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.254

> <EXACT_MASS>
240.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.37203880626734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.792238693666666

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.004204874397633

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.797975509382687

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939949415557032

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.32800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-hydroxyflavanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11    2                                                       
CONECT   13    9   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2S)-7-Hydroxyflavanone	ChEMBL

Chemical Formula

C₁₅H₁₂O₃

Average Mass

240.2540 Da

Monoisotopic Mass

240.07864 Da

IUPAC Name

(2S)-7-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-7-hydroxyflavanone

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-8,14,16H,9H2/t14-/m0/s1

InChI Key

SWAJPHCXKPCPQZ-AWEZNQCLSA-N

Experimental Spectra

Not Available

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

Species Name	Source	Reference
Ceratiola ericoides	Plant	KNApSAcK
Crinum asiaticum	LOTUS Database	35616633
Cryptocarya chinensis	LOTUS Database	35616633
Dalbergia cochinchinensis	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Diplotropis purpurea	Plant	KNApSAcK
Dracaena cinnabari	LOTUS Database	35616633
Flourensia heterolepis	Plant	KNApSAcK
Muntingia calabura	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Phyllanthus sellowianus	Plant	KNApSAcK
Platymiscium praecox	Plant	KNApSAcK
Pterocarpus marsupium	Plant	KNApSAcK
Vachellia vernicosa	LOTUS Database	35616633
Vatairea heteroptera	Plant	KNApSAcK
Virgilia oroboides	Plant	KNApSAcK
Virola surinamensis	Plant	KNApSAcK
Zuccagnia punctata	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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyflavanone (CHEBI:41888 )

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	3.27	ALOGPS
logP	2.79	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.33 m³·mol⁻¹	ChemAxon
Polarizability	25.37 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

Not Available

DrugBank ID

DB04274

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688857

PDB ID

Not Available

ChEBI ID

41888

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-Hydroxyflavanone (NP0055474)

MOL for NP0055474 (7-Hydroxyflavanone)

3D MOL for NP0055474 (7-Hydroxyflavanone)

3D SDF for NP0055474 (7-Hydroxyflavanone)

3D-SDF for NP0055474 (7-Hydroxyflavanone)

PDB for NP0055474 (7-Hydroxyflavanone)

3D PDB for NP0055474 (7-Hydroxyflavanone)

SMILES for NP0055474 (7-Hydroxyflavanone)

INCHI for NP0055474 (7-Hydroxyflavanone)

Structure for NP0055474 (7-Hydroxyflavanone)

3D Structure for NP0055474 (7-Hydroxyflavanone)