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Showing NP-Card for (z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium (NP0154228)

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Record Information
Version2.0
Created at2022-09-02 11:00:45 UTC
Updated at2022-09-02 11:00:45 UTC
NP-MRD IDNP0154228
Secondary Accession NumbersNone
Natural Product Identification
Common Name(z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium
DescriptionNitrosofungin belongs to the class of organic compounds known as propargyl-type 1,3-dipolar organic compounds. These are organic 1,3-dipolar compounds with the general structure X#N+-Z- <-> X-=N+=Z <-> X-=N-Z+ <-> X-N=Z (X = C or O, Z = C, N, or O). (z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium is found in Micromonospora chalcea and Streptomyces plicatus. (z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium was first documented in 1983 (PMID: 6360971). Based on a literature review very few articles have been published on Nitrosofungin (PMID: 6885643).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)


  Mrv1652309022213002D          

  8  7  0  0  0  0            999 V2000
    0.8250    1.4289    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
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  5  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
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3D MOL for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)

     RDKit          3D

 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.2319    1.6731   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344    0.3804    0.2738 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4554   -0.4583   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391   -1.6231    0.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -0.3316   -0.0047 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.3331   -0.7340   -1.2609 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7720   -0.6008    0.9418 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -1.2757    0.7351 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8094    1.9741   -0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7866    1.5723   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507    2.5014    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    0.6351    1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844   -0.7480   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849    0.0997    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550   -1.8327    1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.2320   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  3 13  1  0
  3 14  1  0
  4 15  1  0
  8 16  1  0
M  CHG  2   5   1   6  -1
M  END
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3D SDF for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)


  Mrv1652309022213002D          

  8  7  0  0  0  0            999 V2000
    0.8250    1.4289    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
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  5  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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0154228

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H8N2O3/c1-3(2-6)5(8)4-7/h3,6-7H,2H2,1H3/b5-4-

> <INCHI_KEY>
IDWDQTUMRSGLSV-PLNGDYQASA-N

> <FORMULA>
C3H8N2O3

> <MOLECULAR_WEIGHT>
120.108

> <EXACT_MASS>
120.053492126

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.848737628539066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(Z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium

> <ALOGPS_LOGP>
-1.01

> <JCHEM_LOGP>
-2.3014888211384124

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.080577291135459

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0077996262216455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.200418937982783

> <JCHEM_POLAR_SURFACE_AREA>
78.89

> <JCHEM_REFRACTIVITY>
28.1304

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)

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PDB for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   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  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       1.540   0.000   0.000  0.00  0.00           N+1
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O-1
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)
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SMILES for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)
CC(CO)[N+](\[O-])=N\O
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INCHI for NP0154228 ((z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium)
InChI=1S/C3H8N2O3/c1-3(2-6)5(8)4-7/h3,6-7H,2H2,1H3/b5-4-
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View in JSmol
Synonyms
ValueSource
2-N-Nitrosohydroxylamino-1-propanolMeSH
Chemical FormulaC3H8N2O3
Average Mass120.1080 Da
Monoisotopic Mass120.05349 Da
IUPAC Name(Z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium
Traditional Name(Z)-(hydroxyimino)(1-hydroxypropan-2-yl)oxidoazanium
CAS Registry NumberNot Available
SMILES
CC(CO)[N+](\[O-])=N\O
InChI Identifier
InChI=1S/C3H8N2O3/c1-3(2-6)5(8)4-7/h3,6-7H,2H2,1H3/b5-4-
InChI KeyIDWDQTUMRSGLSV-PLNGDYQASA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Micromonospora chalceaLOTUS Database
Streptomyces plicatusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as propargyl-type 1,3-dipolar organic compounds. These are organic 1,3-dipolar compounds with the general structure  X#N+-Z- <-> X-=N+=Z <-> X-=N-Z+ <-> X-N=Z (X = C or O, Z = C, N, or O).
KingdomOrganic compounds  
Super ClassOrganic 1,3-dipolar compounds  
ClassPropargyl-type 1,3-dipolar organic compounds  
Sub ClassNot Available
Direct ParentPropargyl-type 1,3-dipolar organic compounds  
Alternative Parents
Substituents
  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Allyl-type 1,3-dipolar organic compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic zwitterion
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-2.3ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.89 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.13 m³·mol⁻¹ChemAxon
Polarizability10.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135455430  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dolak LA, Castle TM, Hannon BR, Argoudelis AD, Reusser F: Fermentation, isolation, characterization and structure of nitrosofungin. J Antibiot (Tokyo). 1983 Nov;36(11):1425-30. doi: 10.7164/antibiotics.36.1425. [PubMed:6360971  ] 
  2. Dolak LA, Castle TM: The synthesis of nitrosofungin, a new antibiotic. J Antibiot (Tokyo). 1983 Jul;36(7):916-7. doi: 10.7164/antibiotics.36.916. [PubMed:6885643  ] 
  3. LOTUS database [Link]