NP-MRD: Showing NP-Card for 5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid (NP0150900)

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Record Information

Version

2.0

Created at

2022-09-02 07:08:13 UTC

Updated at

2022-09-02 07:08:14 UTC

NP-MRD ID

NP0150900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

Description

5-Acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3. 5-Acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500572D          

 42 46  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241500572D          

 42 46  0  0  0  0            999 V2000
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 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
  9 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  0  0  0  0
 25 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  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 35 39  2  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  2  0  0  0  0
 25 42  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0150900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(C)C(=CC2=C1OC1=C(C2=O)C(C(O)=O)=C(O)C(O)=C1)C(O)=C1COC2=CC(O)=C(O)C(C(O)=O)=C2C1=O

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

> <INCHI_KEY>
VZJACTNXARYXEM-UHFFFAOYSA-N

> <FORMULA>
C28H18O14

> <MOLECULAR_WEIGHT>
578.438

> <EXACT_MASS>
578.06965526

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
54.78748839527936

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
3.0708313873333335

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.33995439911659

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.423137746645001

> <JCHEM_PKA_STRONGEST_BASIC>
-6.582102617734841

> <JCHEM_POLAR_SURFACE_AREA>
245.41999999999996

> <JCHEM_REFRACTIVITY>
141.7413

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -17.338  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    4    9                                                  
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    7   26   42                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   39                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   35   29   40                                                  
CONECT   40   39   26   41                                                  
CONECT   41   40                                                            
CONECT   42   25                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
5-Acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate	Generator

Chemical Formula

C₂₈H₁₈O₁₄

Average Mass

578.4380 Da

Monoisotopic Mass

578.06966 Da

IUPAC Name

5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

Traditional Name

5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2H-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(C)C(=CC2=C1OC1=C(C2=O)C(C(O)=O)=C(O)C(O)=C1)C(O)=C1COC2=CC(O)=C(O)C(C(O)=O)=C2C1=O

InChI Identifier

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

InChI Key

VZJACTNXARYXEM-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Not Available

Direct Parent

Homoisoflavonoids

Alternative Parents

Substituents

Homoisoflavonoid
Xanthone
Dibenzopyran
Xanthene
Chromone
Chromane
Benzopyran
Hydroxybenzoic acid
Salicylic acid or derivatives
1-benzopyran
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Enol
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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	2.11	ALOGPS
logP	3.07	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	245.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.74 m³·mol⁻¹	ChemAxon
Polarizability	54.79 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

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

85061730

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid (NP0150900)

MOL for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D MOL for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D SDF for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D-SDF for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

PDB for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D PDB for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

SMILES for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

INCHI for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

Structure for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)

3D Structure for NP0150900 (5-acetyl-7-[(5-carboxy-6,7-dihydroxy-4-oxo-2h-1-benzopyran-3-ylidene)(hydroxy)methyl]-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid)