NP-MRD: Showing NP-Card for (2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid (NP0156235)

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Record Information

Version

2.0

Created at

2022-09-02 13:25:05 UTC

Updated at

2022-09-02 13:25:05 UTC

NP-MRD ID

NP0156235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid

Description

87695-80-5 Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Based on a literature review very few articles have been published on 87695-80-5.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215252D          

 38 40  0  0  0  0            999 V2000
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022215252D          

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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  2  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 14 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0156235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C\C=C\C=C\C=C\C(O)=NC1=CC(O)(\C=C\C=C\C=C\C(O)=NC2=C(O)CCC2=O)C2OC2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32N2O7/c1-19(2)12-8-4-3-5-9-13-23(34)30-20-18-29(37,28-27(38-28)26(20)36)17-11-7-6-10-14-24(35)31-25-21(32)15-16-22(25)33/h3-11,13-14,17-19,27-28,32,37H,12,15-16H2,1-2H3,(H,30,34)(H,31,35)/b5-3+,7-6+,8-4+,13-9+,14-10+,17-11+

> <INCHI_KEY>
GLLPHENDWDLKRH-GXCWGJJBSA-N

> <FORMULA>
C29H32N2O7

> <MOLECULAR_WEIGHT>
520.582

> <EXACT_MASS>
520.220951378

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
58.310451082113936

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E)-N-{5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-C-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.695124406333332

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.1408170772349475

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.526282436272375

> <JCHEM_PKA_STRONGEST_BASIC>
1.9725153311353858

> <JCHEM_POLAR_SURFACE_AREA>
152.31

> <JCHEM_REFRACTIVITY>
152.92900000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E)-N-{5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-C-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.991  -0.410   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.011  -0.410   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.538  -1.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.548  -3.037   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.075  -4.484   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.085  -5.663   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.611  -7.111   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.622  -8.290   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.105  -8.023   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       2.148  -9.737   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.158 -10.917   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.531 -12.411   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.959 -12.988   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.225 -13.227   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.955 -12.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.378 -10.810   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.194  -9.504   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.001   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                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   37                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
CONECT   34   16   35   36                                                  
CONECT   35   34   36                                                       
CONECT   36   35   34   37                                                  
CONECT   37   36   14   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂N₂O₇

Average Mass

520.5820 Da

Monoisotopic Mass

520.22095 Da

IUPAC Name

(2E,4E,6E)-N-{5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-C-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)C\C=C\C=C\C=C\C(O)=NC1=CC(O)(\C=C\C=C\C=C\C(O)=NC2=C(O)CCC2=O)C2OC2C1=O

InChI Identifier

InChI=1S/C29H32N2O7/c1-19(2)12-8-4-3-5-9-13-23(34)30-20-18-29(37,28-27(38-28)26(20)36)17-11-7-6-10-14-24(35)31-25-21(32)15-16-22(25)33/h3-11,13-14,17-19,27-28,32,37H,12,15-16H2,1-2H3,(H,30,34)(H,31,35)/b5-3+,7-6+,8-4+,13-9+,14-10+,17-11+

InChI Key

GLLPHENDWDLKRH-GXCWGJJBSA-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 cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
N-acyl-amine
Tertiary alcohol
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4	ALOGPS
logP	3.7	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	5.53	ChemAxon
pKa (Strongest Basic)	1.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	152.31 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	152.93 m³·mol⁻¹	ChemAxon
Polarizability	58.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018519

Chemspider ID

4944204

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid (NP0156235)

MOL for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

3D MOL for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

3D SDF for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

3D-SDF for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

PDB for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

3D PDB for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

SMILES for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

INCHI for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

Structure for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)

3D Structure for NP0156235 ((2e,4e,6e)-n-{5-hydroxy-5-[(1e,3e,5e)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)-c-hydroxycarbonimidoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}-9-methyldeca-2,4,6-trienimidic acid)