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Showing NP-Card for Muscapurpurin (NP0050758)

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Record Information
Version2.0
Created at2022-04-27 22:05:28 UTC
Updated at2022-04-27 22:05:28 UTC
NP-MRD IDNP0050758
Secondary Accession NumbersNone
Natural Product Identification
Common NameMuscapurpurin
Description(2S)-2,5-dicarboxy-1-{2-[(2S)-2-carboxy-6-carboxylato-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H,7H-1λ⁵-pyrano[3,4-b]pyrrol-1-ylium belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Muscapurpurin is found in Amanita muscaria . Based on a literature review very few articles have been published on (2S)-2,5-dicarboxy-1-{2-[(2S)-2-carboxy-6-carboxylato-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H,7H-1λ⁵-pyrano[3,4-b]pyrrol-1-ylium.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050758 (Muscapurpurin)


  Mrv1652304282200052D          

 30 32  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -4.5039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9702   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -5.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813   -3.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112   -5.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -5.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1957   -4.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 O   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  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  CHG  2   5   1  22  -1
M  END
Download

3D MOL for NP0050758 (Muscapurpurin)

Download
3D SDF for NP0050758 (Muscapurpurin)

  Mrv1652304282200052D          

 30 32  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633   -4.5039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9702   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -4.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -5.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813   -3.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6112   -5.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -5.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1957   -4.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 O   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  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  1 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  CHG  2   5   1  22  -1
M  END
> <DATABASE_ID>
NP0050758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1C\C(=C/C=[N+]2\[C@@H](CC3=C2C(=O)OC(=C3)C(O)=O)C([O-])=O)C=C(N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H14N2O10/c21-14(22)9-3-7(4-10(19-9)15(23)24)1-2-20-11(16(25)26)5-8-6-12(17(27)28)30-18(29)13(8)20/h1-3,6,10-11H,4-5H2,(H4,21,22,23,24,25,26,27,28)/t10-,11-/m0/s1

> <INCHI_KEY>
KAUZSNIDLZSFSR-QWRGUYRKSA-N

> <FORMULA>
C18H14N2O10

> <MOLECULAR_WEIGHT>
418.314

> <EXACT_MASS>
418.064844659

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.678646582725904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,2S)-5-carboxy-1-{2-[(2S,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H,7H-1lambda5-pyrano[3,4-b]pyrrol-1-ylium-2-carboxylate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
-4.4647158463946495

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.06213434263779

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7860761822819708

> <JCHEM_PKA_STRONGEST_BASIC>
0.06743066005312792

> <JCHEM_POLAR_SURFACE_AREA>
193.36999999999998

> <JCHEM_REFRACTIVITY>
120.16969999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,2S)-5-carboxy-1-{2-[(2S,4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H-1lambda5-pyrano[3,4-b]pyrrol-1-ylium-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050758 (Muscapurpurin)
Download
PDB for NP0050758 (Muscapurpurin)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.726  -5.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.696  -6.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.171  -8.407   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -3.678  -8.727   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.708  -7.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.232  -6.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.215  -7.903   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.690  -9.368   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -7.245  -6.759   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.141  -9.552   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.617 -11.016   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.365  -9.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.483  -2.637   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.483   0.031   0.000  0.00  0.00           O-1
HETATM   23  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.198   1.777   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.531  -0.533   0.000  0.00  0.00           O+0
CONECT    1    2    5   26                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    4   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25    1   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Download
3D PDB for NP0050758 (Muscapurpurin)
Download
SMILES for NP0050758 (Muscapurpurin)
OC(=O)[C@@H]1C\C(=C/C=[N+]2\[C@@H](CC3=C2C(=O)OC(=C3)C(O)=O)C([O-])=O)C=C(N1)C(O)=O
Download
INCHI for NP0050758 (Muscapurpurin)
InChI=1S/C18H14N2O10/c21-14(22)9-3-7(4-10(19-9)15(23)24)1-2-20-11(16(25)26)5-8-6-12(17(27)28)30-18(29)13(8)20/h1-3,6,10-11H,4-5H2,(H4,21,22,23,24,25,26,27,28)/t10-,11-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H14N2O10
Average Mass418.3140 Da
Monoisotopic Mass418.06484 Da
IUPAC Name(1E,2S)-5-carboxy-1-{2-[(2S,4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H,7H-1lambda5-pyrano[3,4-b]pyrrol-1-ylium-2-carboxylate
Traditional Name(1E,2S)-5-carboxy-1-{2-[(2S,4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-7-oxo-1H,2H,3H-1lambda5-pyrano[3,4-b]pyrrol-1-ylium-2-carboxylate
CAS Registry NumberNot Available
SMILES
OC(=O)[C@@H]1C\C(=C/C=[N+]2\[C@@H](CC3=C2C(=O)OC(=C3)C(O)=O)C([O-])=O)C=C(N1)C(O)=O
InChI Identifier
InChI=1S/C18H14N2O10/c21-14(22)9-3-7(4-10(19-9)15(23)24)1-2-20-11(16(25)26)5-8-6-12(17(27)28)30-18(29)13(8)20/h1-3,6,10-11H,4-5H2,(H4,21,22,23,24,25,26,27,28)/t10-,11-/m0/s1
InChI KeyKAUZSNIDLZSFSR-QWRGUYRKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amanita muscariaFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassTetracarboxylic acids and derivatives  
Direct ParentTetracarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • L-alpha-amino acid
    • 

  • Pyranone
    • 

  • Tetrahydropyridine
    • 

  • Hydropyridine
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Amino acid or derivatives
    • 

  • Carboxylic acid salt
    • 

  • Amino acid
    • 

  • Lactone
    • 

  • Shiff base
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Enamine
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic salt
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic zwitterion
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.9ALOGPS
logP-4.5ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)1.79ChemAxon
pKa (Strongest Basic)0.067ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area193.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.17 m³·mol⁻¹ChemAxon
Polarizability38.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001602  
Chemspider ID10128210  
KEGG Compound IDC08563  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441634  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available