NP-MRD: Showing NP-Card for (3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid (NP0322440)

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Record Information

Version

2.0

Created at

2022-09-12 01:12:16 UTC

Updated at

2022-09-12 01:12:17 UTC

NP-MRD ID

NP0322440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid

Description

FK409, also known as nor-3 CPD, belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl). (3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid is found in Streptomyces griseosporeus. (3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid was first documented in 2007 (PMID: 17959957). Based on a literature review a small amount of articles have been published on FK409 (PMID: 25152034) (PMID: 22387484) (PMID: 19000699) (PMID: 18391852).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
    3.1964   -3.2053   -0.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897   -2.4485   -0.3621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7671   -1.2310   -0.6621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0356   -0.9374   -1.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969   -0.2052   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4334   -0.6635   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6019    0.1056    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787    1.5281   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    2.3685    1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -0.4672    0.6524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0326   -0.2778   -0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038   -1.8241    1.0595 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.4874   -2.6931    0.4846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9772   -2.2485    2.0710 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.0812    0.9484   -0.8319 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    1.3000   -1.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8239   -1.4125   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -1.7264    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    1.9551   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5621    1.7073   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1046    2.2087    1.9015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8711    3.4339    0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989    2.1553    1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1400    0.1370    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130   -1.0339   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5004    0.7304   -0.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7143   -0.4828   -1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765    2.2791   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 15  2  0
 15 16  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
  8 19  1  0
  8 20  1  0
  6 18  1  0
 16 28  1  0
  4 17  1  0
  2  1  1  0
 10 24  1  1
 11 25  1  0
 11 26  1  0
 11 27  1  0
M  CHG  2  12   1  14  -1
M  END


  Mrv1652309122203122D          

 15 14  0  0  0  0            999 V2000
    3.3000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.0000    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
    1.2375    0.7145    0.0000 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  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    2.1434    0.0000 C   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    2.1434    0.0000 O   0  0  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
  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  2  0  0  0  0
  6  7  1  4  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END
> <DATABASE_ID>
NP0322440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(=C/C(=NO)C(O)=N)C(C)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13N3O4/c1-3-6(5(2)11(14)15)4-7(10-13)8(9)12/h4-5,13H,3H2,1-2H3,(H2,9,12)/b6-4+,10-7?

> <INCHI_KEY>
MZAGXDHQGXUDDX-MXRGZUMGSA-N

> <FORMULA>
C8H13N3O4

> <MOLECULAR_WEIGHT>
215.209

> <EXACT_MASS>
215.090605911

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
19.850750472901503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid

> <JCHEM_LOGP>
-1.0431253670613576

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.2112588486335

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.580642041728663

> <JCHEM_PKA_STRONGEST_BASIC>
11.348529713779891

> <JCHEM_POLAR_SURFACE_AREA>
119.81

> <JCHEM_REFRACTIVITY>
63.29

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.540  -2.667   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.160   2.667   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
4-Ethyl-2-(hydroxyimino)-5-nitro-3-hexenamide	MeSH
4-Ethyl-2-hydroxyimino-5-nitro-3-hexenamide	MeSH
4-Ethyl-2-hydroxyimino-5-nitro-3-hexenecarboxamide	MeSH
NOR-3 CPD	MeSH
NOR3 hexenamide CPD	MeSH
Ethyl-2-(hydroxyamino)-5-nitro-3-hexenamide	MeSH

Chemical Formula

C₈H₁₃N₃O₄

Average Mass

215.2090 Da

Monoisotopic Mass

215.09061 Da

IUPAC Name

(3E)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid

Traditional Name

(3E)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid

CAS Registry Number

Not Available

SMILES

CC\C(=C/C(=NO)C(O)=N)C(C)[N+]([O-])=O

InChI Identifier

InChI=1S/C8H13N3O4/c1-3-6(5(2)11(14)15)4-7(10-13)8(9)12/h4-5,13H,3H2,1-2H3,(H2,9,12)/b6-4+,10-7?

InChI Key

MZAGXDHQGXUDDX-MXRGZUMGSA-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
Streptomyces griseosporeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl).

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Oximes

Direct Parent

Ketoximes

Alternative Parents

Substituents

Ketoxime
Carboxamide group
C-nitro compound
Organic nitro compound
Primary carboxylic acid amide
Carboxylic acid derivative
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Carbonyl group
Organic zwitterion
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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
logP	-1	ChemAxon
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	11.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.29 m³·mol⁻¹	ChemAxon
Polarizability	19.85 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86742405

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ueshima S, Nishida T, Koike M, Matsuda H, Sawa Y, Uchiyama Y: Nitric oxide-mediated injury of interstitial cells of Cajal and intestinal dysmotility under endotoxemia of mice. Biomed Res. 2014;35(4):251-62. doi: 10.2220/biomedres.35.251. [PubMed:25152034 ]
Ruef P, Craciun E, Frommhold D, Kuss N, Fritzsching B, Poschl J, Koch L: The NO-donor FK409 improves mechanical properties of activated neonatal PMN. Clin Hemorheol Microcirc. 2012;51(4):293-301. doi: 10.3233/CH-2012-1536. [PubMed:22387484 ]
Ito Y, Okuda S, Ohkawa F, Kato S, Mitsufuji S, Yoshikawa T, Takeuchi K: Dual role of nitric oxide in gastric hypersecretion in the distended stomach: inhibition of acid secretion and stimulation of pepsinongen secretion. Life Sci. 2008 Dec 19;83(25-26):886-92. doi: 10.1016/j.lfs.2008.10.010. Epub 2008 Oct 30. [PubMed:19000699 ]
Wang Y, Crisostomo PR, Wang M, Weil B, Abarbanell A, Poynter J, Manukyan MC, Meldrum DR: Nitric oxide suppresses the secretion of vascular endothelial growth factor and hepatocyte growth factor from human mesenchymal stem cells. Shock. 2008 Nov;30(5):527-31. doi: 10.1097/SHK.0b013e31816f1ec9. [PubMed:18391852 ]
Guarda IF, Saad WA, de Arruda Camargo LA: Nitric oxide and angiotensin II receptors mediate the pressor effect of angiotensin II: a study in conscious and zoletil-anesthetized rats. Anesth Analg. 2007 Nov;105(5):1293-7, table of contents. doi: 10.1213/01.ane.0000282782.30891.c5. [PubMed:17959957 ]
LOTUS database [Link]

Showing NP-Card for (3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid (NP0322440)

MOL for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

3D MOL for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

3D SDF for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

3D-SDF for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

PDB for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

3D PDB for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

SMILES for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

INCHI for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

Structure for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)

3D Structure for NP0322440 ((3e)-4-ethyl-2-(hydroxyimino)-5-nitrohex-3-enimidic acid)