NP-MRD: Showing NP-Card for 2H-1-Benzopyran-7-yloxy (NP0138399)

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Record Information

Version

1.0

Created at

2022-05-31 17:57:47 UTC

Updated at

2022-05-31 17:57:47 UTC

NP-MRD ID

NP0138399

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2H-1-Benzopyran-7-yloxy

Description

7-Hydroxyflavanone 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. Thus, 7-hydroxyflavanone is considered to be a flavonoid lipid molecule. 2H-1-Benzopyran-7-yloxy is found in Berberis dictyota, Ceratiola ericoides, Crinum asiaticum, Cryptocarya chinensis, Dalbergia cochinchinensis, Dalbergia sissoo, Dracaena cinnabari, Heliotropium indicum, Muntingia calabura, Ononis natrix, Oxytropis falcata, Phyllanthus sellowianus, Pterocarpus marsupium, Vachellia vernicosa, Virgilia oroboides, Virola surinamensis and Zuccagnia punctata. 7-Hydroxyflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.5221    2.0093   -2.4317 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369    1.1703   -1.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3038    0.8523   -1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796    0.6513    0.0763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0067    0.2573    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9171    1.1091    0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470    0.7595    0.9824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7163   -0.4640    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048   -1.3155   -0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4673   -0.9674   -0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2053   -0.4827    0.4792 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5796   -0.3571    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012   -1.0004    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627   -0.8525    0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674   -1.5266    1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3436   -0.0393   -0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    0.6206   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784    0.4611   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -0.1341   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9556    1.6313   -1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3206    1.5147    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5354    2.0822    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9553    1.4439    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7569   -0.7531    0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1311   -2.2835   -0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7515   -1.6260   -0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756   -1.6370    1.8641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1038   -2.4692    1.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037    0.0898   -0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172    1.2556   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 18  2  0
 18 17  1  0
 17 16  2  0
 18  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  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
 16 14  1  0
 10  5  1  0
 11 12  1  0
 15 28  1  0
 13 27  1  0
 17 30  1  0
 16 29  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  1
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
M  END


  Mrv1652310051722282D          

 18 20  0  0  0  0            999 V2000
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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   -0.0000    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
    1.4289    0.8250    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138399

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C(=O)CC(O2)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

> <INCHI_KEY>
SWAJPHCXKPCPQZ-UHFFFAOYSA-N

> <FORMULA>
C15H12O3

> <MOLECULAR_WEIGHT>
240.258

> <EXACT_MASS>
240.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.371981770958186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
7.797975509211127

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939949415614574

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.328

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxyflavanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   11   15                                                       
CONECT    9   13   14                                                       
CONECT   10    4    5   14                                                  
CONECT   11    6    8   16                                                  
CONECT   12    7   13   15                                                  
CONECT   13    9   12   17                                                  
CONECT   14    9   10   18                                                  
CONECT   15    8   12   18                                                  
CONECT   16   11                                                            
CONECT   17   13                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydro-7-hydroxy-2-phenyl-4H-1-benzopyran-4-one	ChEBI

Chemical Formula

C₁₅H₁₂O₃

Average Mass

240.2580 Da

Monoisotopic Mass

240.07864 Da

IUPAC Name

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

Traditional Name

7-hydroxyflavanone

CAS Registry Number

41680-08-4

SMILES

OC1=CC2=C(C=C1)C(=O)CC(O2)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

InChI Key

SWAJPHCXKPCPQZ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Berberis dictyota	LOTUS Database	35616633
Ceratiola ericoides	LOTUS Database	35616633
Crinum asiaticum	LOTUS Database	35616633
Cryptocarya chinensis	LOTUS Database	35616633
Dalbergia cochinchinensis	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Dracaena cinnabari	LOTUS Database	35616633
Heliotropium indicum	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Ononis natrix	LOTUS Database	35616633
Oxytropis falcata	LOTUS Database	35616633
Phyllanthus sellowianus	LOTUS Database	35616633
Pterocarpus marsupium	LOTUS Database	35616633
Vachellia vernicosa	LOTUS Database	35616633
Virgilia oroboides	LOTUS Database	35616633
Virola surinamensis	LOTUS Database	35616633
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

monohydroxyflavanone (CHEBI:34483 )
flavanones (C14290 )
Flavanones (LMPK12140018 )

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

HMDB0153774

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008126

Chemspider ID

Not Available

KEGG Compound ID

C14290

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

34483

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2H-1-Benzopyran-7-yloxy (NP0138399)

MOL for NP0138399 (2H-1-Benzopyran-7-yloxy)

3D MOL for NP0138399 (2H-1-Benzopyran-7-yloxy)

3D SDF for NP0138399 (2H-1-Benzopyran-7-yloxy)

3D-SDF for NP0138399 (2H-1-Benzopyran-7-yloxy)

PDB for NP0138399 (2H-1-Benzopyran-7-yloxy)

3D PDB for NP0138399 (2H-1-Benzopyran-7-yloxy)

SMILES for NP0138399 (2H-1-Benzopyran-7-yloxy)

INCHI for NP0138399 (2H-1-Benzopyran-7-yloxy)

Structure for NP0138399 (2H-1-Benzopyran-7-yloxy)

3D Structure for NP0138399 (2H-1-Benzopyran-7-yloxy)