NP-MRD: Showing NP-Card for FK409 (NP0013958)

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Record Information

Version

2.0

Created at

2021-01-05 23:14:21 UTC

Updated at

2021-07-15 17:15:56 UTC

NP-MRD ID

NP0013958

Secondary Accession Numbers

None

Natural Product Identification

Common Name

FK409

Provided By

NPAtlas

Description

Nor-3 is also known as nor-3 CPD. FK409 is found in Streptomyces griseosporeus. FK409 was first documented in 1989 (PMID: 2584141). Based on a literature review very few articles have been published on nor-3 (PMID: 33970717).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119513D          

 28 27  0  0  0  0            999 V2000
   -1.3730   -1.8922   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751   -0.8751    0.6430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5352    0.4624    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000    1.0239   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960    0.4729   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    1.3904   -0.3109 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1824    1.0538   -0.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -0.8601    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -1.0467    0.1939 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -1.9556    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019    1.2956   -0.0626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6995    0.6897   -1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    1.3268    1.2568 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.5952    0.8718    1.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7922    1.8637    2.3339 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.4647   -1.8303   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715   -2.9200    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967   -1.9859   -1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437   -1.2978    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -0.6940    1.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304    2.1086   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826    0.9703   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -0.8339    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4025   -1.3877   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    2.3256   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.0030   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    1.4917   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.2353   -0.5401 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  2  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  4 21  1  0  0  0  0
  7 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 11 25  1  6  0  0  0
 12 26  1  0  0  0  0
 12 27  1  0  0  0  0
 12 28  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END


  Mrv1652306242119513D          

 28 27  0  0  0  0            999 V2000
   -1.3730   -1.8922   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751   -0.8751    0.6430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5352    0.4624    0.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000    1.0239   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8960    0.4729   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8637    1.3904   -0.3109 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1824    1.0538   -0.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -0.8601    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -1.0467    0.1939 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -1.9556    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019    1.2956   -0.0626 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6995    0.6897   -1.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    1.3268    1.2568 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.5952    0.8718    1.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7922    1.8637    2.3339 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.4647   -1.8303   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715   -2.9200    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9967   -1.9859   -1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437   -1.2978    1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -0.6940    1.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5304    2.1086   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826    0.9703   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3058   -0.8339    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4025   -1.3877   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494    2.3256   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1879   -0.0030   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1323    1.4917   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5771    0.2353   -0.5401 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  2  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  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
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  4 21  1  0  0  0  0
  7 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 11 25  1  6  0  0  0
 12 26  1  0  0  0  0
 12 27  1  0  0  0  0
 12 28  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END
> <DATABASE_ID>
NP0013958

> <DATABASE_NAME>
NP-MRD

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

> <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-/t5-/m1/s1

> <INCHI_KEY>
MZAGXDHQGXUDDX-JSRXJHBZSA-N

> <FORMULA>
C8H13N3O4

> <MOLECULAR_WEIGHT>
215.209

> <EXACT_MASS>
215.090605911

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.477371129191418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(2R,3E,5Z)-5-carbamoyl-3-ethyl-5-(hydroxyimino)pent-3-en-2-yl]nitro}-lambda1-oxidanyl

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.7824846436666667

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.180902159481466

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.856665111465776

> <JCHEM_PKA_STRONGEST_BASIC>
0.2484511628329933

> <JCHEM_POLAR_SURFACE_AREA>
118.82000000000002

> <JCHEM_REFRACTIVITY>
52.3534

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3E,5Z)-5-carbamoyl-3-ethyl-5-(hydroxyimino)pent-3-en-2-ylnitro]-lambda1-oxidanyl

> <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      -1.373  -1.892  -0.189  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.675  -0.875   0.643  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.535   0.462   0.140  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.600   1.024  -0.152  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.896   0.473  -0.065  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.864   1.390  -0.311  0.00  0.00           N+0
HETATM    7  O   UNK     0       4.182   1.054  -0.275  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.397  -0.860   0.055  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.851  -1.047   0.194  0.00  0.00           N+0
HETATM   10  O   UNK     0       1.811  -1.956   0.066  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.802   1.296  -0.063  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.700   0.690  -1.074  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.452   1.327   1.257  0.00  0.00           N+1
HETATM   14  O   UNK     0      -3.595   0.872   1.408  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.792   1.864   2.334  0.00  0.00           O-1
HETATM   16  H   UNK     0      -2.465  -1.830  -0.228  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.172  -2.920   0.255  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.997  -1.986  -1.230  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.044  -1.298   1.325  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.562  -0.694   1.481  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.530   2.109  -0.534  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.683   0.970  -1.165  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.306  -0.834   1.098  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.402  -1.388  -0.610  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.549   2.326  -0.360  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.188  -0.003  -1.739  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.132   1.492  -1.720  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.577   0.235  -0.540  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3   19   20                                             
CONECT    3    2    4   11                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   22                                                       
CONECT    8    5    9   10                                                  
CONECT    9    8   23   24                                                  
CONECT   10    8                                                            
CONECT   11    3   12   13   25                                             
CONECT   12   11   26   27   28                                             
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    2                                                            
CONECT   21    4                                                            
CONECT   22    7                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   12                                                            
CONECT   28   12                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol View NMR Assignments

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

{[(2R,3E,5Z)-5-carbamoyl-3-ethyl-5-(hydroxyimino)pent-3-en-2-yl]nitro}-lambda1-oxidanyl

Traditional Name

[(2R,3E,5Z)-5-carbamoyl-3-ethyl-5-(hydroxyimino)pent-3-en-2-ylnitro]-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

CC\C(=C/C(=N/O)/C(N)=O)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-JSRXJHBZSA-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
Ayapana amygdalina	KNApSAcK Database	22123792
Streptomyces griseosporeus	NPAtlas	2584141

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	0.31	ALOGPS
logP	0.78	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	0.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.35 m³·mol⁻¹	ChemAxon
Polarizability	20.48 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001283

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023405

Chemspider ID

4920759

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6413529

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hino M, Ando T, Takase S, Itoh Y, Okamoto M, Kohsaka M, Aoki H, Imanaka H: FK409, a novel vasodilator isolated from the acid-treated fermentation broth of Streptomyces griseosporeus. II. Structure of FK409 and its precursor FR-900411. J Antibiot (Tokyo). 1989 Nov;42(11):1584-8. doi: 10.7164/antibiotics.42.1584. [PubMed:2584141 ]
Khusnutdinova E, Galimova Z, Lobov A, Baikova I, Kazakova O, Thu HNT, Tuyen NV, Gatilov Y, Csuk R, Serbian I, Hoenke S: Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential. Nat Prod Res. 2021 May 10:1-10. doi: 10.1080/14786419.2021.1922904. [PubMed:33970717 ]

Showing NP-Card for FK409 (NP0013958)

MOL for NP0013958 (FK409)

3D MOL for NP0013958 (FK409)

3D SDF for NP0013958 (FK409)

3D-SDF for NP0013958 (FK409)

PDB for NP0013958 (FK409)

3D PDB for NP0013958 (FK409)

SMILES for NP0013958 (FK409)

INCHI for NP0013958 (FK409)

Structure for NP0013958 (FK409)

3D Structure for NP0013958 (FK409)