NP-MRD: Showing NP-Card for 5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde (NP0059792)

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Record Information

Version

2.0

Created at

2022-04-28 04:58:38 UTC

Updated at

2022-04-28 04:58:38 UTC

NP-MRD ID

NP0059792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde

Description

Unonal belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, unonal is considered to be a flavonoid lipid molecule. 5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde is found in Dasymaschalon rostratum, Desmos chinensis , Desmos cochinchinensis and Unona lawii. Unonal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -1.2290    0.1405    2.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162    0.1301    1.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1694    0.1934    0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392    0.2700    1.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001    0.1832   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1420    0.2500   -0.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725    0.3199    0.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8174    0.1058   -1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.0977   -2.7070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    0.0421   -1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.0349   -2.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9213   -0.0504   -3.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -0.0963   -2.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.0812   -0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7012   -0.1438   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506   -0.2214   -1.3607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9948   -0.2804   -1.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3533   -0.2596    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4014   -0.1810    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.1228    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663   -0.0065    0.2304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9356    0.0535    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    1.1387    2.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -0.6159    3.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1734   -0.1286    2.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6395    0.2771    2.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4883    0.2375   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330    0.0540   -3.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5016   -0.1552   -2.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4104   -0.2408   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294   -0.3420   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4004   -0.3049    0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7009   -0.1660    2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2975   -0.0618    1.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  5  8  2  0
  8  9  1  0
  8 10  1  0
 10 22  2  0
 22 21  1  0
 21 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 22  2  1  0
 20 15  1  0
 11 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1533004161507062D          

 22 24  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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    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
    1.4289    0.0000    0.0000 C   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
    2.1434   -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  0  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
    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 10 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C=O)=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O5/c1-9-15(20)11(8-18)16(21)14-12(19)7-13(22-17(9)14)10-5-3-2-4-6-10/h2-8,20-21H,1H3

> <INCHI_KEY>
IGNBNJUVMNCTNB-UHFFFAOYSA-N

> <FORMULA>
C17H12O5

> <MOLECULAR_WEIGHT>
296.278

> <EXACT_MASS>
296.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.94308482722372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-8-methyl-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
4.536178189333333

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.496835184499774

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.973468706699964

> <JCHEM_PKA_STRONGEST_BASIC>
-5.383219144092675

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
82.55820000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
unonal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   10                                                  
CONECT   17   14   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-6-formyl-8-methylflavone	MeSH

Chemical Formula

C₁₇H₁₂O₅

Average Mass

296.2780 Da

Monoisotopic Mass

296.06847 Da

IUPAC Name

5,7-dihydroxy-8-methyl-4-oxo-2-phenyl-4H-chromene-6-carbaldehyde

Traditional Name

unonal

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(C=O)=C(O)C2=C1OC(=CC2=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H12O5/c1-9-15(20)11(8-18)16(21)14-12(19)7-13(22-17(9)14)10-5-3-2-4-6-10/h2-8,20-21H,1H3

InChI Key

IGNBNJUVMNCTNB-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, 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
Dasymaschalon rostratum	Plant	KNApSAcK
Desmos chinensis	Plant	KNApSAcK
Desmos cochinchinensis	Plant	KNApSAcK
Unona lawii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Phenol
Pyranone
Aryl-aldehyde
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110176 )

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	3.46	ALOGPS
logP	4.54	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	29.94 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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde (NP0059792)

MOL for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

3D MOL for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

3D SDF for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

3D-SDF for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

PDB for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

3D PDB for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

SMILES for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

INCHI for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

Structure for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)

3D Structure for NP0059792 (5,7-Dihydroxy-8-methyl-4-oxo-2-phenyl-4H-1-benzopyran-6-carboxaldehyde)