NP-MRD: Showing NP-Card for 2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde (NP0190732)

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Record Information

Version

2.0

Created at

2022-09-04 07:27:33 UTC

Updated at

2022-09-04 07:27:33 UTC

NP-MRD ID

NP0190732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde

Description

Desmal belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. 2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde is found in Desmos chinensis. Desmal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.1050    0.1949    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    0.3031    0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980    1.5346    0.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8365    2.6162    0.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    1.6542   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9373    2.8912   -0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5772    4.0052   -0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018    0.4858   -0.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -0.7702    0.0987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635   -0.8742    0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5339   -2.0634    0.3356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6856   -1.9704    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0728   -3.0579    0.5899 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051   -1.8151   -0.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2454   -0.5806    0.2853 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9584   -0.7826    1.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.3938    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    0.4304    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7639    0.6174    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4396   -0.0149   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197   -0.8504   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681   -1.0241   -0.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    0.5306   -0.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3221   -0.6202    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4504   -0.1961   -0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5772    1.1416    0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773    3.5758   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228    2.9839   -0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -2.9572    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073   -1.6694   -1.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3497   -2.6646   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906    0.0919    2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8908    0.9445    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177    1.2620    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5012    0.0919   -0.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -1.3674   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431   -1.6826   -1.6126 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 23  1  0
 23 15  1  0
 15 16  1  1
 15 14  1  0
 14 12  1  0
 12 13  2  0
 12  9  1  0
  9 10  2  0
 10 11  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 10  2  1  0
 22 17  1  0
  9  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 16 32  1  0
 14 30  1  0
 14 31  1  0
 11 29  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
M  END


  Mrv1533004161504512D          

 23 25  0  0  0  0            999 V2000
    0.0000   -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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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 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
    3.8545    0.3627    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -0.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0098   -0.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -1.3310    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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 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 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(C=O)=C2OC(O)(CC(=O)C2=C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c1-9-14(20)11(8-18)16-13(15(9)21)12(19)7-17(22,23-16)10-5-3-2-4-6-10/h2-6,8,20-22H,7H2,1H3

> <INCHI_KEY>
PTQOJHUHQGPAFD-UHFFFAOYSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.293

> <EXACT_MASS>
314.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.55082540644497

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-carbaldehyde

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
3.824913064333333

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.023268771270653

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.885172561507016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.59615783984725

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
82.40140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3H-1-benzopyran-8-carbaldehyde

> <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       0.000  -3.080   0.000  0.00  0.00           C+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   0.000   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  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.195   0.677   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.175   0.142   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.691  -0.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.218  -1.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.228  -2.752   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.712  -2.485   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   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
CONECT   18   10   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
8-Formyl-2,5,7-trihydroxy-6-methyl-flavanone	MeSH
8-Formyl-2,5,7-trihydroxy-6-methylflavanone	MeSH

Chemical Formula

C₁₇H₁₄O₆

Average Mass

314.2930 Da

Monoisotopic Mass

314.07904 Da

IUPAC Name

2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-8-carbaldehyde

Traditional Name

2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3H-1-benzopyran-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(C=O)=C2OC(O)(CC(=O)C2=C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14O6/c1-9-14(20)11(8-18)16-13(15(9)21)12(19)7-17(22,23-16)10-5-3-2-4-6-10/h2-6,8,20-22H,7H2,1H3

InChI Key

PTQOJHUHQGPAFD-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
Desmos chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Aryl-aldehyde
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Hemiacetal
Polyol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aldehyde
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.78	ALOGPS
logP	3.82	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.4 m³·mol⁻¹	ChemAxon
Polarizability	30.55 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

10018499

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde (NP0190732)

MOL for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

3D MOL for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

3D SDF for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

3D-SDF for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

PDB for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

3D PDB for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

SMILES for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

INCHI for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

Structure for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)

3D Structure for NP0190732 (2,5,7-trihydroxy-6-methyl-4-oxo-2-phenyl-3h-1-benzopyran-8-carbaldehyde)