NP-MRD: Showing NP-Card for Pseudopurpurin (NP0051634)

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Record Information

Version

2.0

Created at

2022-04-27 22:55:49 UTC

Updated at

2022-04-27 22:55:49 UTC

NP-MRD ID

NP0051634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudopurpurin

Description

1,3,4-Trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system. Pseudopurpurin is found in Asperula spp., Galium rubioides, Galium spp., Relbunium spp., Rubia akane, Rubia cordifolia , Rubia tinctorum and Sherardia arvensis. 1,3,4-Trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.1776    0.1429    0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1979   -0.5847    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4114   -1.8514    0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8545   -0.1161    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6156    1.1585   -0.3956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7225    1.9333   -0.6865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506    1.6344   -0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.8867   -1.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2657    0.8063   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4640   -0.4721    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7562   -0.9150    0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -2.1578    0.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7100   -1.2785    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5902   -2.4314    0.9741 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0810   -0.7729    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -1.5477    0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4680   -1.0844    0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6596    0.1905   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624    0.9704   -0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2806    0.4911   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0983    1.2894   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    2.4500   -0.9460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7698   -2.6208    0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6095    2.8458   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848    3.5486   -1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -2.8760    1.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325   -2.5472    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3557   -1.6590    0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6620    0.5897   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    1.9777   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  2  0
 13 10  1  0
 10 11  2  0
 11 12  1  0
 11  4  1  0
 10  9  1  0
 15 20  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
 19 30  1  0
 18 29  1  0
 17 28  1  0
 16 27  1  0
 12 26  1  0
M  END


  Mrv1533004171523232D          

 22 24  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 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
    2.1434   -0.4125    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(O)C(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O7/c16-10-5-3-1-2-4-6(5)11(17)8-7(10)12(18)9(15(21)22)14(20)13(8)19/h1-4,18-20H,(H,21,22)

> <INCHI_KEY>
OOKBSCGBRWBGFL-UHFFFAOYSA-N

> <FORMULA>
C15H8O7

> <MOLECULAR_WEIGHT>
300.222

> <EXACT_MASS>
300.027002598

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
27.25609505499221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,4-trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
4.265593017666667

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.519034759911765

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252277742329914

> <JCHEM_PKA_STRONGEST_BASIC>
-5.60768973927843

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
74.34989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pseudopurpurin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    9   21                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
1,3,4-Trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate	Generator

Chemical Formula

C₁₅H₈O₇

Average Mass

300.2220 Da

Monoisotopic Mass

300.02700 Da

IUPAC Name

1,3,4-trihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

Traditional Name

pseudopurpurin

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(O)C(O)=C2C(=O)C3=CC=CC=C3C(=O)C2=C1O

InChI Identifier

InChI=1S/C15H8O7/c16-10-5-3-1-2-4-6(5)11(17)8-7(10)12(18)9(15(21)22)14(20)13(8)19/h1-4,18-20H,(H,21,22)

InChI Key

OOKBSCGBRWBGFL-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
Asperula spp.	Plant	KNApSAcK
Galium rubioides	LOTUS Database	35616633
Galium spp.	Plant	KNApSAcK
Relbunium spp.	Plant	KNApSAcK
Rubia akane	LOTUS Database	35616633
Rubia cordifolia	Plant	KNApSAcK
Rubia tinctorum	Plant	KNApSAcK
Sherardia arvensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenecarboxylic acids. These are organic compounds containing a carboxylic acid group attached to an anthracene ring system.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Anthracenecarboxylic acids and derivatives

Direct Parent

Anthracenecarboxylic acids

Alternative Parents

Substituents

Anthracene carboxylic acid
9,10-anthraquinone
Anthraquinone
Hydroxyanthraquinone
2-naphthalenecarboxylic acid or derivatives
2-naphthalenecarboxylic acid
Trihydroxybenzoic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Aryl ketone
Vinylogous acid
Ketone
Carboxylic acid derivative
Carboxylic acid
Polyol
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:8608 )
Anthraquinone type (C10394 )

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	2.12	ALOGPS
logP	4.27	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	27.26 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

C00002856

Chemspider ID

Not Available

KEGG Compound ID

C10394

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442765

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pseudopurpurin (NP0051634)

MOL for NP0051634 (Pseudopurpurin)

3D MOL for NP0051634 (Pseudopurpurin)

3D SDF for NP0051634 (Pseudopurpurin)

3D-SDF for NP0051634 (Pseudopurpurin)

PDB for NP0051634 (Pseudopurpurin)

3D PDB for NP0051634 (Pseudopurpurin)

SMILES for NP0051634 (Pseudopurpurin)

INCHI for NP0051634 (Pseudopurpurin)

Structure for NP0051634 (Pseudopurpurin)

3D Structure for NP0051634 (Pseudopurpurin)