NP-MRD: Showing NP-Card for (1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid (NP0327804)

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Record Information

Version

1.0

Created at

2022-09-12 10:42:54 UTC

Updated at

2022-09-12 10:42:54 UTC

NP-MRD ID

NP0327804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid

Description

ZINC3782944 belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. (1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid is found in Mallotus repandus, Pelargonium reniforme, Phyllanthus flexuosus, Phyllanthus niruri and Punica granatum. Based on a literature review very few articles have been published on ZINC3782944.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.6494    1.9599   -1.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199    1.1809   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7296   -0.3425   -1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -0.5698   -0.3276 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2403   -1.7616    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3397   -2.8637   -0.3203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291   -1.8857    1.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405    0.2767   -0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078    1.4165   -1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344    2.4367   -1.3668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7106    2.4929   -0.9827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577    3.4771   -1.1937 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    1.4105   -0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632    1.4148    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1036    0.3362    0.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    0.3581    1.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3668   -0.7982    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -1.8516    1.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0505   -0.7949    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132   -1.9074    0.8997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4952    0.2727   -0.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.6716   -2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7383   -0.7373   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    0.1745    0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7473   -1.0596    2.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486    2.3065   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0069    1.1681    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612   -2.7157    1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322   -2.7224    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2  9  1  0
  9  8  2  0
  8 21  1  0
 21 19  2  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
  8  4  1  0
 13 21  1  0
 10  9  1  0
  7 25  1  0
  4 24  1  1
  3 22  1  0
  3 23  1  0
 20 29  1  0
 18 28  1  0
 16 27  1  0
 14 26  1  0
M  END


  Mrv1652309122212422D          

 21 23  0  0  1  0            999 V2000
    4.2295   -0.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6996    1.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074    2.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952    2.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937   -1.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 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
 15 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
  8 21  1  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327804

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1CC(=O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)/t3-/m1/s1

> <INCHI_KEY>
JFJWMFPFMLRLMI-GSVOUGTGSA-N

> <FORMULA>
C13H8O8

> <MOLECULAR_WEIGHT>
292.199

> <EXACT_MASS>
292.021917218

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.294324614361802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylic acid

> <JCHEM_LOGP>
0.4143267856666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.685074288983295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9120313762904586

> <JCHEM_PKA_STRONGEST_BASIC>
-6.732237543344348

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
67.03070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-7,8,9-trihydroxy-3,5-dioxo-1H,2H-cyclopenta[c]isochromene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       7.895  -1.070   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.039   3.538   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.561   3.968   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.151   4.604   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.495  -1.800   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.228  -3.205   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.745   0.674   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.790   3.484   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   21                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   13                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₈O₈

Average Mass

292.1990 Da

Monoisotopic Mass

292.02192 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H]1CC(=O)C2=C1C1=C(O)C(O)=C(O)C=C1C(=O)O2

InChI Identifier

InChI=1S/C13H8O8/c14-5-2-4-7(10(17)9(5)16)8-3(12(18)19)1-6(15)11(8)21-13(4)20/h2-3,14,16-17H,1H2,(H,18,19)/t3-/m1/s1

InChI Key

JFJWMFPFMLRLMI-GSVOUGTGSA-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
Mallotus repandus	LOTUS Database	35616633
Pelargonium reniforme	LOTUS Database	35616633
Phyllanthus flexuosus	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Ketone
Lactone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
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

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

57256951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid (NP0327804)

MOL for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

3D MOL for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

3D SDF for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

3D-SDF for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

PDB for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

3D PDB for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

SMILES for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

INCHI for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

Structure for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)

3D Structure for NP0327804 ((1r)-7,8,9-trihydroxy-3,5-dioxo-1h,2h-cyclopenta[c]isochromene-1-carboxylic acid)