NP-MRD: Showing NP-Card for 3-(oximinoacetamido)acrylamide (NP0004877)

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Record Information

Version

1.0

Created at

2020-12-09 02:17:03 UTC

Updated at

2021-07-15 16:50:25 UTC

NP-MRD ID

NP0004877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(oximinoacetamido)acrylamide

Provided By

NPAtlas

Description

3-(oximinoacetamido)acrylamide 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-{[(2Z)-1-hydroxy-2-(hydroxyimino)ethylidene]amino}prop-2-enimidic acid (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 18 17  0  0  0  0            999 V2000
    3.1399   -0.5702    1.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757    0.6183    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8876    1.4934    0.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.8037   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612   -0.1347   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3357   -0.0223   -0.9883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6064   -0.0553   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449   -0.1862    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8025    0.0645   -1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369    0.0310   -0.5760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9484   -0.1133    0.7868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5267   -0.7225    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8607   -1.2650    1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    1.6919   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863   -1.0418    0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    0.0856   -2.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.1784   -2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887   -0.8555    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 16  1  0  0  0  0
  9 17  1  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004877

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H7N3O3/c6-4(9)1-2-7-5(10)3-8-11/h1-3,11H,(H2,6,9)(H,7,10)/b2-1+,8-3-

> <INCHI_KEY>
QSQKMLSXKVSYMJ-PKTZTGOHSA-N

> <FORMULA>
C5H7N3O3

> <MOLECULAR_WEIGHT>
157.129

> <EXACT_MASS>
157.048741097

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.043628371287522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-[(2Z)-2-(hydroxyimino)acetamido]prop-2-enamide

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-1.5835916379999997

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.595017568271434

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.304091262553233

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2057964035086962

> <JCHEM_POLAR_SURFACE_AREA>
104.78

> <JCHEM_REFRACTIVITY>
36.8706

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(2Z)-2-(hydroxyimino)acetamido]prop-2-enamide

> <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       3.140  -0.570   1.327  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.976   0.618   0.574  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.888   1.493   0.617  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.777   0.804  -0.223  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.861  -0.135  -0.233  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.336  -0.022  -0.988  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.606  -0.055  -0.354  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.645  -0.186   0.888  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.803   0.065  -1.179  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.937   0.031  -0.576  0.00  0.00           N+0
HETATM   11  O   UNK     0      -3.948  -0.113   0.787  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.527  -0.723   2.147  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.861  -1.265   1.055  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.609   1.692  -0.812  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.986  -1.042   0.342  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.233   0.086  -2.030  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.728   0.178  -2.271  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.389  -0.856   1.290  0.00  0.00           H+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   18                                                       
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E)-3-{[(2Z)-1-hydroxy-2-(hydroxyimino)ethylidene]amino}prop-2-enimidate	Generator

Chemical Formula

C₅H₇N₃O₃

Average Mass

157.1290 Da

Monoisotopic Mass

157.04874 Da

IUPAC Name

(2E)-3-[(2Z)-2-(hydroxyimino)acetamido]prop-2-enamide

Traditional Name

(2E)-3-[(2Z)-2-(hydroxyimino)acetamido]prop-2-enamide

CAS Registry Number

Not Available

SMILES

NC(=O)\C=C\NC(=O)\C=N/O

InChI Identifier

InChI=1S/C5H7N3O3/c6-4(9)1-2-7-5(10)3-8-11/h1-3,11H,(H2,6,9)(H,7,10)/b2-1+,8-3-

InChI Key

QSQKMLSXKVSYMJ-PKTZTGOHSA-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	-1.3	ALOGPS
logP	-1.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-0.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.87 m³·mol⁻¹	ChemAxon
Polarizability	14.04 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

NPA015171

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4911576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 ]
Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]

Showing NP-Card for 3-(oximinoacetamido)acrylamide (NP0004877)

MOL for NP0004877 (3-(oximinoacetamido)acrylamide)

3D MOL for NP0004877 (3-(oximinoacetamido)acrylamide)

3D SDF for NP0004877 (3-(oximinoacetamido)acrylamide)

3D-SDF for NP0004877 (3-(oximinoacetamido)acrylamide)

PDB for NP0004877 (3-(oximinoacetamido)acrylamide)

3D PDB for NP0004877 (3-(oximinoacetamido)acrylamide)

SMILES for NP0004877 (3-(oximinoacetamido)acrylamide)

INCHI for NP0004877 (3-(oximinoacetamido)acrylamide)

Structure for NP0004877 (3-(oximinoacetamido)acrylamide)

3D Structure for NP0004877 (3-(oximinoacetamido)acrylamide)