NP-MRD: Showing NP-Card for 5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid (NP0211249)

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Record Information

Version

2.0

Created at

2022-09-05 09:26:15 UTC

Updated at

2022-09-05 09:26:15 UTC

NP-MRD ID

NP0211249

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid

Description

2',3'-Dihydrovinaxanthone belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. 5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid is found in Penicillium vinaceum. Based on a literature review very few articles have been published on 2',3'-Dihydrovinaxanthone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211262D          

 42 46  0  0  0  0            999 V2000
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 42  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052211262D          

 42 46  0  0  0  0            999 V2000
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  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 22 26  1  0  0  0  0
  4 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 36 40  2  0  0  0  0
 30 40  1  0  0  0  0
 40 41  1  0  0  0  0
 27 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0211249

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(C2COC3=CC(O)=C(O)C(C(O)=O)=C3C2=O)C(C(C)=O)=C2OC3=CC(O)=C(O)C(C(O)=O)=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H18O14/c1-7(29)9-3-10-22(33)19-15(5-13(32)25(36)21(19)28(39)40)42-26(10)16(8(2)30)17(9)11-6-41-14-4-12(31)24(35)20(27(37)38)18(14)23(11)34/h3-5,11,31-32,35-36H,6H2,1-2H3,(H,37,38)(H,39,40)

> <INCHI_KEY>
ZDXVSCFWCXSQJJ-UHFFFAOYSA-N

> <FORMULA>
C28H18O14

> <MOLECULAR_WEIGHT>
578.438

> <EXACT_MASS>
578.06965526

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
53.895737371021895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxo-9H-xanthene-1-carboxylic acid

> <JCHEM_LOGP>
2.49094805

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.3773020499441246

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4097513216159374

> <JCHEM_PKA_STRONGEST_BASIC>
-6.579190855531086

> <JCHEM_POLAR_SURFACE_AREA>
242.25999999999996

> <JCHEM_REFRACTIVITY>
139.7337

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.907  -8.946   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22    4   27                                                  
CONECT   27   26   28   41                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   36   30   41                                                  
CONECT   41   40   27   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₁₈O₁₄

Average Mass

578.4380 Da

Monoisotopic Mass

578.06966 Da

IUPAC Name

5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxo-9H-xanthene-1-carboxylic acid

Traditional Name

5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(C2COC3=CC(O)=C(O)C(C(O)=O)=C3C2=O)C(C(C)=O)=C2OC3=CC(O)=C(O)C(C(O)=O)=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C28H18O14/c1-7(29)9-3-10-22(33)19-15(5-13(32)25(36)21(19)28(39)40)42-26(10)16(8(2)30)17(9)11-6-41-14-4-12(31)24(35)20(27(37)38)18(14)23(11)34/h3-5,11,31-32,35-36H,6H2,1-2H3,(H,37,38)(H,39,40)

InChI Key

ZDXVSCFWCXSQJJ-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
Penicillium vinaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Hydroxyisoflavonoid
Xanthone
Xanthene
Dibenzopyran
Chromone
Salicylic acid or derivatives
1-benzopyran
Hydroxybenzoic acid
Chromane
Benzopyran
Acetophenone
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	2.49	ChemAxon
pKa (Strongest Acidic)	1.41	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	242.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.73 m³·mol⁻¹	ChemAxon
Polarizability	53.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

7984080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9808321

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid (NP0211249)

MOL for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

3D MOL for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

3D SDF for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

3D-SDF for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

PDB for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

3D PDB for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

SMILES for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

INCHI for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

Structure for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)

3D Structure for NP0211249 (5,7-diacetyl-6-(5-carboxy-6,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl)-2,3-dihydroxy-9-oxoxanthene-1-carboxylic acid)