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Showing NP-Card for fosfomycin (NP0213284)

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Record Information
Version2.0
Created at2022-09-05 12:13:49 UTC
Updated at2022-09-05 12:13:49 UTC
NP-MRD IDNP0213284
Secondary Accession NumbersNone
Natural Product Identification
Common Namefosfomycin
Description(3-Methyloxiran-2-yl)phosphonic acid belongs to the class of organic compounds known as organic phosphonic acids. fosfomycin is found in Streptomyces wedmorensis. These are organic compounds containing phosphonic acid (3-methyloxiran-2-yl)phosphonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0213284 (fosfomycin)


  Mrv1533005011518372D          

  8  8  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013    0.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -0.9526    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
Download

3D MOL for NP0213284 (fosfomycin)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.3485   -0.4499   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2031    0.3248    0.0779 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5517   -0.4760    1.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1376   -0.2057   -0.1035 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6288    0.7503    0.2187 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3005    2.2091    0.4073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7853    0.5636   -1.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    0.2012    1.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362    0.1755   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7499   -1.2263    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -1.0346   -1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    1.3841    0.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -1.0872   -0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923   -0.3536   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611   -0.7754    1.7712 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
  4  5  1  0
  5  7  1  0
  5  8  1  0
  5  6  2  0
  4  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  1
  4 13  1  6
  7 14  1  0
  8 15  1  0
M  END
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3D SDF for NP0213284 (fosfomycin)


  Mrv1533005011518372D          

  8  8  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8888   -0.2382    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -0.6507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013    0.4763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -0.9526    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC1P(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)

> <INCHI_KEY>
YMDXZJFXQJVXBF-UHFFFAOYSA-N

> <FORMULA>
C3H7O4P

> <MOLECULAR_WEIGHT>
138.059

> <EXACT_MASS>
138.008195703

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.815976224545048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-methyloxiran-2-yl)phosphonic acid

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-0.7377748799999998

> <ALOGPS_LOGS>
-0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.82082800096408

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2504967658604222

> <JCHEM_PKA_STRONGEST_BASIC>
-4.306369310142532

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
25.8737

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.69e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosfomycin calcium

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0213284 (fosfomycin)

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PDB for NP0213284 (fosfomycin)
HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.215   0.325   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.325   0.325   0.000  0.00  0.00           C+0
HETATM    5  P   UNK     0      -1.659  -0.445   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      -2.993  -1.215   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.429   0.889   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.889  -1.778   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    4                                                       
CONECT    4    3    2    5                                                  
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0213284 (fosfomycin)
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SMILES for NP0213284 (fosfomycin)
CC1OC1P(O)(O)=O
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INCHI for NP0213284 (fosfomycin)
InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)
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View in JSmol
Synonyms
ValueSource
(3-Methyloxiran-2-yl)phosphonateGenerator
1,2-EPOXYPROPYLPHOSPHONateGenerator
FosfomycinMeSH
MonurilMeSH
PhosphonomycinMeSH
Fosfomycin tromethamineMeSH
Fosfomycin trometamol saltMeSH
PhosphomycinMeSH
Tromethamine, fosfomycinMeSH
Chemical FormulaC3H7O4P
Average Mass138.0590 Da
Monoisotopic Mass138.00820 Da
IUPAC Name(3-methyloxiran-2-yl)phosphonic acid
Traditional Namefosfomycin calcium
CAS Registry NumberNot Available
SMILES
CC1OC1P(O)(O)=O
InChI Identifier
InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)
InChI KeyYMDXZJFXQJVXBF-UHFFFAOYSA-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
Streptomyces wedmorensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic phosphonic acids and derivatives  
Sub ClassOrganic phosphonic acids  
Direct ParentOrganic phosphonic acids  
Alternative Parents
Substituents
  • Organophosphonic acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Oxirane
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organophosphorus compound
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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-0.86ALOGPS
logP-0.74ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.87 m³·mol⁻¹ChemAxon
Polarizability10.82 ųChemAxon
Number of Rings1ChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]