NP-MRD: Showing NP-Card for (e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium (NP0237751)

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Record Information

Version

2.0

Created at

2022-09-06 20:59:16 UTC

Updated at

2022-09-06 20:59:16 UTC

NP-MRD ID

NP0237751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium

Description

Enteromycin belongs to the class of organic compounds known as alpha-imino acid and derivatives. These are organic acids containing an imino group attached to a carbon, which in turn is immediately linked to a carboxyl group (or a derivative thereof). (e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium was first documented in 2021 (PMID: 33885295). Based on a literature review very few articles have been published on Enteromycin (PMID: 33782561).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222592D          

 13 12  0  0  0  0            999 V2000
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   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  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0237751

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O5/c1-13-8(12)4-5(9)7-3-2-6(10)11/h2-4H,1H3,(H,7,9)(H,10,11)/b3-2+,8-4+

> <INCHI_KEY>
UBAVPHLFRVPRCI-CRBCFSCISA-N

> <FORMULA>
C6H8N2O5

> <MOLECULAR_WEIGHT>
188.139

> <EXACT_MASS>
188.043321366

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.804836727956136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(E)-{[(Z)-[(1E)-2-carboxyeth-1-en-1-yl]-C-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium

> <JCHEM_LOGP>
-2.8372054735392016

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.669964879765905

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6128622629590668

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9971239364867767

> <JCHEM_POLAR_SURFACE_AREA>
105.19000000000001

> <JCHEM_REFRACTIVITY>
51.9102

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(E)-{[(Z)-[(1E)-2-carboxyeth-1-en-1-yl]-C-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.160   2.667   0.000  0.00  0.00           N+1
HETATM    4  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O-1
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.620   0.000   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₆H₈N₂O₅

Average Mass

188.1390 Da

Monoisotopic Mass

188.04332 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H8N2O5/c1-13-8(12)4-5(9)7-3-2-6(10)11/h2-4H,1H3,(H,7,9)(H,10,11)/b3-2+,8-4+

InChI Key

UBAVPHLFRVPRCI-CRBCFSCISA-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 alpha-imino acid and derivatives. These are organic acids containing an imino group attached to a carbon, which in turn is immediately linked to a carboxyl group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-imino acid and derivatives

Direct Parent

Alpha-imino acid and derivatives

Alternative Parents

Substituents

Alpha-imino acid or derivatives
Vinylogous amide
Acrylic acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Organic zwitterion
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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

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

4517425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5365404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Igarashi Y, Matsuyuki Y, Yamada M, Fujihara N, Harunari E, Oku N, Karim MRU, Yang T, Yamada K, Imada C, Fukaya K, Urabe D: Structure Determination, Biosynthetic Origin, and Total Synthesis of Akazaoxime, an Enteromycin-Class Metabolite from a Marine-Derived Actinomycete of the Genus Micromonospora. J Org Chem. 2021 May 7;86(9):6528-6537. doi: 10.1021/acs.joc.1c00358. Epub 2021 Apr 22. [PubMed:33885295 ]
He HY, Ryan KS: Glycine-derived nitronates bifurcate to O-methylation or denitrification in bacteria. Nat Chem. 2021 Jun;13(6):599-606. doi: 10.1038/s41557-021-00656-8. Epub 2021 Mar 29. [PubMed:33782561 ]
LOTUS database [Link]

Showing NP-Card for (e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium (NP0237751)

MOL for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

3D MOL for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

3D SDF for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

3D-SDF for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

PDB for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

3D PDB for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

SMILES for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

INCHI for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

Structure for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)

3D Structure for NP0237751 ((e)-{[(z)-[(1e)-2-carboxyeth-1-en-1-yl]-c-hydroxycarbonimidoyl]methylidene}(methoxy)oxidoazanium)