NP-MRD: Showing NP-Card for 4-(O-methyl-aci-nitro)crotonic acid (NP0004878)

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Record Information

Version

1.0

Created at

2020-12-09 02:17:06 UTC

Updated at

2021-07-15 16:50:25 UTC

NP-MRD ID

NP0004878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(O-methyl-aci-nitro)crotonic acid

Provided By

NPAtlas

Description

4-(O-methyl-aci-nitro)crotonic acid is found in Streptomyces sp. It was first documented in 1965 (PMID: 14342596). Based on a literature review very few articles have been published on (2E)-3-carboxy-N-methoxyprop-2-enimine oxide (PMID: 34072889) (PMID: 34023282) (PMID: 34015832) (PMID: 33873017).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 17 16  0  0  0  0            999 V2000
   -3.8329    0.3281    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933   -0.5383    0.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4492    0.0113    0.0530 N   0  3  0  0  0  4  0  0  0  0  0  0
   -1.3600    1.2551   -0.5492 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.3597   -0.5895    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9172    0.0529    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0388   -0.5524    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3289    0.0474    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012    1.1665   -0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4857   -0.6090    0.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213    0.7648    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635    1.0764   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7629   -0.2218    0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891   -1.5602    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    1.0286   -0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488   -1.5318    0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3572   -0.1282    0.7530 H   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
 10 17  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0004878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])\C(\[H])=[N+](/[O-])OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO4/c1-10-6(9)4-2-3-5(7)8/h2-4H,1H3,(H,7,8)/b3-2+,6-4+

> <INCHI_KEY>
HBAKIZJZZAZTAP-WJPDYIDTSA-N

> <FORMULA>
C5H7NO4

> <MOLECULAR_WEIGHT>
145.114

> <EXACT_MASS>
145.037507709

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.34987401353066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(E)-[(2E)-3-carboxyprop-2-en-1-ylidene](methoxy)oxidoazanium

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-3.2307306014717456

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.668203286716008

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.272440703292716

> <JCHEM_PKA_STRONGEST_BASIC>
-6.084273870778252

> <JCHEM_POLAR_SURFACE_AREA>
72.6

> <JCHEM_REFRACTIVITY>
43.8434

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-[(2E)-3-carboxyprop-2-en-1-ylidene](methoxy)oxidoazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.833   0.328   0.298  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.693  -0.538   0.291  0.00  0.00           O+0
HETATM    3  N   UNK     0      -1.449   0.011   0.053  0.00  0.00           N+1
HETATM    4  O   UNK     0      -1.360   1.255  -0.549  0.00  0.00           O-1
HETATM    5  C   UNK     0      -0.360  -0.590   0.371  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.917   0.053   0.089  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.039  -0.552   0.410  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.329   0.047   0.150  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.401   1.167  -0.393  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.486  -0.609   0.496  0.00  0.00           O+0
HETATM   11  H   UNK     0      -3.921   0.765   1.311  0.00  0.00           H+0
HETATM   12  H   UNK     0      -3.664   1.076  -0.494  0.00  0.00           H+0
HETATM   13  H   UNK     0      -4.763  -0.222   0.032  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.389  -1.560   0.842  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.954   1.029  -0.384  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.949  -1.532   0.884  0.00  0.00           H+0
HETATM   17  H   UNK     0       5.357  -0.128   0.753  0.00  0.00           H+0
CONECT    1    2   11   12   13                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   17                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    7                                                            
CONECT   17   10                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₅H₇NO₄

Average Mass

145.1140 Da

Monoisotopic Mass

145.03751 Da

IUPAC Name

(E)-[(2E)-3-carboxyprop-2-en-1-ylidene](methoxy)oxidoazanium

Traditional Name

(E)-[(2E)-3-carboxyprop-2-en-1-ylidene](methoxy)oxidoazanium

CAS Registry Number

Not Available

SMILES

CO\[N+]([O-])=C\C=C\C(O)=O

InChI Identifier

InChI=1S/C5H7NO4/c1-10-6(9)4-2-3-5(7)8/h2-4H,1H3,(H,7,8)/b3-2+,6-4+

InChI Key

HBAKIZJZZAZTAP-WJPDYIDTSA-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
Streptomyces sp.	NPAtlas	14342596

Chemical Taxonomy

Classification

Not classified

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	0.09	ALOGPS
logP	-3.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.84 m³·mol⁻¹	ChemAxon
Polarizability	13.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001914

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32989975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78582598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

WILEY PF, HERR RR, MACKELLAR FA, ARGOUDELIS AD: THREE CHEMICALLY RELATED METABOLITES OF STREPTOMYCES. II. STRUCTURAL STUDIES. J Org Chem. 1965 Jul;30:2330-4. doi: 10.1021/jo01018a051. [PubMed:14342596 ]
Mesonero-Escuredo S, Morales J, Mainar-Jaime RC, Diaz G, Arnal JL, Casanovas C, Barrabes S, Segales J: Effect of Edema Disease Vaccination on Mortality and Growth Parameters in Nursery Pigs in a Shiga Toxin 2e Positive Commercial Farm. Vaccines (Basel). 2021 May 31;9(6). pii: vaccines9060567. doi: 10.3390/vaccines9060567. [PubMed:34072889 ]
Bezerra de Oliveira Filho G, Verissimo de Oliveira Cardoso M, Caroline da Silva Santos A, Ramos Dos Santos TA, Cristovao-Silva AC, Rubio LG, da Silva Maia Neto L, Leite PG, Machado FS, Alves LC, Brayner FA, Alves Pereira VR, Lima Leite AC: Structural design, synthesis and anti-Trypanosoma cruzi profile of the second generation of 4-thiazolidinones chlorine derivatives. Chem Biol Interact. 2021 Aug 25;345:109514. doi: 10.1016/j.cbi.2021.109514. Epub 2021 May 21. [PubMed:34023282 ]
Wang J, Yan H, Huo X, Li L, Wang H, Zhang M, Li X, Zhao Y, Chen G, Si J: New Sulfoxide-Containing Derivatives from the Resin of Ferula sinkiangensis. Planta Med. 2021 May 20. doi: 10.1055/a-1495-5963. [PubMed:34015832 ]
Li XR, Liu J, Peng C, Zhou QM, Liu F, Guo L, Xiong L: Polyacetylene glucosides from the florets of Carthamus tinctorius and their anti-inflammatory activity. Phytochemistry. 2021 Jul;187:112770. doi: 10.1016/j.phytochem.2021.112770. Epub 2021 Apr 16. [PubMed:33873017 ]

Showing NP-Card for 4-(O-methyl-aci-nitro)crotonic acid (NP0004878)

MOL for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

3D MOL for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

3D SDF for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

3D-SDF for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

PDB for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

3D PDB for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

SMILES for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

INCHI for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

Structure for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)

3D Structure for NP0004878 (4-(O-methyl-aci-nitro)crotonic acid)