NP-MRD: Showing NP-Card for 4-formylaminooxyvinylglycine (NP0009519)

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Record Information

Version

2.0

Created at

2021-01-05 00:16:30 UTC

Updated at

2021-07-15 17:03:29 UTC

NP-MRD ID

NP0009519

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-formylaminooxyvinylglycine

Provided By

NPAtlas

Description

2-Amino-4-formylaminooxy-but-3e-enoic acid, also known as 4-formylaminooxyvinylglycine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 4-formylaminooxyvinylglycine is found in Pseudomonas fluorescens and Pseudomonas fluorescens WH6. 4-formylaminooxyvinylglycine was first documented in 2010 (PMID: 20979386). Based on a literature review very few articles have been published on 2-amino-4-formylaminooxy-but-3e-enoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106363D          

 19 18  0  0  0  0            999 V2000
   -2.2331    1.0980    0.8770 N   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7636    0.0264   -0.0370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3579   -0.3323    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840    0.1698   -0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9405   -0.2984   -0.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707    0.1063   -0.0497 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4342    0.5213    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4527    0.1656    0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6870   -1.1033    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140   -2.3205    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615   -0.8758    0.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356    0.8219    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    1.2513    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540    0.4390   -1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187   -1.0792    0.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    0.9160   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979   -1.0924    0.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6479    1.5310   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4183    0.0552   -0.0114 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  2 14  1  6  0  0  0
  3 15  1  0  0  0  0
  4 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7 18  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])[H])C(\[H])=C(/[H])ON([H])C([H])=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8N2O4/c6-4(5(9)10)1-2-11-7-3-8/h1-4H,6H2,(H,7,8)(H,9,10)/b2-1+/t4-/m0/s1

> <INCHI_KEY>
BICCALWGKRVQAV-QPHDTYRISA-N

> <FORMULA>
C5H8N2O4

> <MOLECULAR_WEIGHT>
160.129

> <EXACT_MASS>
160.048406746

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.685976007964985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3E)-2-amino-4-(formamidooxy)but-3-enoic acid

> <ALOGPS_LOGP>
-2.77

> <JCHEM_LOGP>
-3.772328755186445

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.554102882741276

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7792779656515432

> <JCHEM_PKA_STRONGEST_BASIC>
8.514834221456894

> <JCHEM_POLAR_SURFACE_AREA>
101.64999999999999

> <JCHEM_REFRACTIVITY>
34.850100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3E)-2-amino-4-(formamidooxy)but-3-enoic acid

> <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  N   UNK     0      -2.233   1.098   0.877  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.764   0.026  -0.037  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.358  -0.332   0.157  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.684   0.170  -0.443  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.940  -0.298  -0.139  0.00  0.00           O+0
HETATM    6  N   UNK     0       3.171   0.106  -0.050  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.434   0.521   0.043  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.453   0.166   0.540  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.687  -1.103   0.005  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.314  -2.321   0.001  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.061  -0.876   0.063  0.00  0.00           O+0
HETATM   12  H   UNK     0      -3.136   0.822   1.356  0.00  0.00           H+0
HETATM   13  H   UNK     0      -1.450   1.251   1.549  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.854   0.439  -1.070  0.00  0.00           H+0
HETATM   15  H   UNK     0      -0.119  -1.079   0.946  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.566   0.916  -1.150  0.00  0.00           H+0
HETATM   17  H   UNK     0       3.498  -1.092   0.672  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.648   1.531  -0.498  0.00  0.00           H+0
HETATM   19  H   UNK     0      -4.418   0.055  -0.011  0.00  0.00           H+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3    9   14                                             
CONECT    3    2    4   15                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   19                                                       
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    2                                                            
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    6                                                            
CONECT   18    7                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-4-formylaminooxy-but-3E-enoate	Generator
4-Formylaminooxyvinylglycine	MeSH
(2S,3E)-2-Amino-4-{[(hydroxymethylidene)amino]oxy}but-3-enoate	Generator

Chemical Formula

C₅H₈N₂O₄

Average Mass

160.1290 Da

Monoisotopic Mass

160.04841 Da

IUPAC Name

(2S,3E)-2-amino-4-(formamidooxy)but-3-enoic acid

Traditional Name

(2S,3E)-2-amino-4-(formamidooxy)but-3-enoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](\C=C\ONC=O)C(O)=O

InChI Identifier

InChI=1S/C5H8N2O4/c6-4(5(9)10)1-2-11-7-3-8/h1-4H,6H2,(H,7,8)(H,9,10)/b2-1+/t4-/m0/s1

InChI Key

BICCALWGKRVQAV-QPHDTYRISA-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
Pseudomonas fluorescens	LOTUS Database	35616633
Pseudomonas fluorescens WH6	NPAtlas	20979386

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Unsaturated fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:70420 )

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	-2.8	ALOGPS
logP	-3.8	ChemAxon
logS	-0.81	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	8.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	101.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.85 m³·mol⁻¹	ChemAxon
Polarizability	14.69 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

NPA018485

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28288253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McPhail KL, Armstrong DJ, Azevedo MD, Banowetz GM, Mills DI: 4-Formylaminooxyvinylglycine, an herbicidal germination-arrest factor from Pseudomonas rhizosphere bacteria. J Nat Prod. 2010 Nov 29;73(11):1853-7. doi: 10.1021/np1004856. Epub 2010 Oct 27. [PubMed:20979386 ]

Showing NP-Card for 4-formylaminooxyvinylglycine (NP0009519)

MOL for NP0009519 (4-formylaminooxyvinylglycine)

3D MOL for NP0009519 (4-formylaminooxyvinylglycine)

3D SDF for NP0009519 (4-formylaminooxyvinylglycine)

3D-SDF for NP0009519 (4-formylaminooxyvinylglycine)

PDB for NP0009519 (4-formylaminooxyvinylglycine)

3D PDB for NP0009519 (4-formylaminooxyvinylglycine)

SMILES for NP0009519 (4-formylaminooxyvinylglycine)

INCHI for NP0009519 (4-formylaminooxyvinylglycine)

Structure for NP0009519 (4-formylaminooxyvinylglycine)

3D Structure for NP0009519 (4-formylaminooxyvinylglycine)