NP-MRD: Showing NP-Card for methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate (NP0290276)

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Record Information

Version

1.0

Created at

2022-09-09 20:52:56 UTC

Updated at

2022-09-09 20:52:57 UTC

NP-MRD ID

NP0290276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate

Description

Methyl (2E)-1,3-benzothiazol-2(3H)-ylidene(cyano)acetate, also known as ac1NRZ8n, belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom). Methyl (2E)-1,3-benzothiazol-2(3H)-ylidene(cyano)acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on methyl (2E)-1,3-benzothiazol-2(3H)-ylidene(cyano)acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092222522D          

 16 17  0  0  0  0            999 V2000
   -1.8212    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962   -2.1269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  3  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 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
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(\C#N)=C1/NC2=CC=CC=C2S1

> <INCHI_IDENTIFIER>
InChI=1S/C11H8N2O2S/c1-15-11(14)7(6-12)10-13-8-4-2-3-5-9(8)16-10/h2-5,13H,1H3/b10-7+

> <INCHI_KEY>
SEIUOPPGQAMYGB-JXMROGBWSA-N

> <FORMULA>
C11H8N2O2S

> <MOLECULAR_WEIGHT>
232.26

> <EXACT_MASS>
232.03064868

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
23.142712538977168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-cyano-2-[(2E)-2,3-dihydro-1,3-benzothiazol-2-ylidene]acetate

> <JCHEM_LOGP>
2.1511654973333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.813355235130768

> <JCHEM_PKA_STRONGEST_BASIC>
-7.296439495181181

> <JCHEM_POLAR_SURFACE_AREA>
62.120000000000005

> <JCHEM_REFRACTIVITY>
73.006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(2E)-3H-1,3-benzothiazol-2-ylidene]-2-cyanoacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.400   1.365   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.630   0.031   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.320   1.365   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.860  -3.970   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       2.126  -2.549   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
AC1NRZ8n	ChEBI
Methyl (2E)-2-(3H-1,3-benzothiazol-2-ylidene)-2-cyanoacetate	ChEBI
Methyl (2E)-2-(3H-1,3-benzothiazol-2-ylidene)-2-cyanoacetic acid	Generator
Methyl (2E)-1,3-benzothiazol-2(3H)-ylidene(cyano)acetic acid	Generator

Chemical Formula

C₁₁H₈N₂O₂S

Average Mass

232.2600 Da

Monoisotopic Mass

232.03065 Da

IUPAC Name

methyl 2-cyano-2-[(2E)-2,3-dihydro-1,3-benzothiazol-2-ylidene]acetate

Traditional Name

methyl 2-[(2E)-3H-1,3-benzothiazol-2-ylidene]-2-cyanoacetate

CAS Registry Number

Not Available

SMILES

COC(=O)C(\C#N)=C1/NC2=CC=CC=C2S1

InChI Identifier

InChI=1S/C11H8N2O2S/c1-15-11(14)7(6-12)10-13-8-4-2-3-5-9(8)16-10/h2-5,13H,1H3/b10-7+

InChI Key

SEIUOPPGQAMYGB-JXMROGBWSA-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

Alternative Parents

Substituents

Benzo-thiazole
1,2-benzothiazole
1,3-benzothiazole
Aryl thioether
Secondary aliphatic/aromatic amine
Benzenoid
Vinylogous thioester
Thiazole
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Ketene acetal or derivatives
Azacycle
Secondary amine
Carboxylic acid derivative
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiazoles (CHEBI:74935 )
nitrile (CHEBI:74935 )
methyl ester (CHEBI:74935 )

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	2.15	ChemAxon
pKa (Strongest Acidic)	10.81	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.01 m³·mol⁻¹	ChemAxon
Polarizability	23.14 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

4483308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5325824

PDB ID

Not Available

ChEBI ID

74935

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate (NP0290276)

MOL for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

3D MOL for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

3D SDF for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

3D-SDF for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

PDB for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

3D PDB for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

SMILES for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

INCHI for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

Structure for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)

3D Structure for NP0290276 (methyl 2-[(2e)-3h-1,3-benzothiazol-2-ylidene]-2-cyanoacetate)