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Showing NP-Card for basta (NP0290800)

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Record Information
Version2.0
Created at2022-09-09 21:38:47 UTC
Updated at2022-09-09 21:38:47 UTC
NP-MRD IDNP0290800
Secondary Accession NumbersNone
Natural Product Identification
Common Namebasta
DescriptionGlufosinate, also known as phosphinothricin or glufosinic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glufosinate or its ammonium salt Glufosinate is an active ingredient in several nonselective systemic herbicides such as Basta, Rely, Finale, Ignite, Challenge, and Liberty. Glufosinate irreversibly inhibits the enzyme glutamine synthetase, which decreases ammonia detoxification. Glufosinate is a very strong basic compound (based on its pKa). Glufosinate is a potentially toxic compound. Glufosinate-treated plants die due to a buildup of ammonia and a cessation of photosynthesis due to lack of glutamine. It interferes with the glutamine biosynthetic pathway that binds to the glutamate site of the enzyme. basta is found in Streptomyces hygroscopicus. Increased ammonia levels lead to impairment of photorespiration and photosynthesis in plants.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0290800 (basta)


  Mrv0541 02241204112D          

 11 10  0  0  0  0            999 V2000
    1.7605    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for NP0290800 (basta)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
   -2.4335    1.4023   -0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488   -0.3707   -0.5269 P   0  0  2  0  0  5  0  0  0  0  0  0
   -2.8065   -1.0781   -1.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436   -0.8491    0.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765   -0.7340   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3150    0.1345    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954   -0.1807    0.5541 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0111   -1.5719    0.9061 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    0.1574   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844   -0.7445   -1.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4048    1.4123   -1.3012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7773    1.7487   -1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859    1.5750   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    1.9724    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263   -0.4332    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -0.5769   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -1.8094   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0809   -0.1104    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    1.1933    0.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    0.4356    1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -2.1043   -0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -1.7204    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7634    2.2521   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  4  1  1
  2  3  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  1
  8 21  1  0
  8 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0290800 (basta)


  Mrv0541 02241204112D          

 11 10  0  0  0  0            999 V2000
    1.7605    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    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
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0290800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CP(O)(=O)CCC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
IAJOBQBIJHVGMQ-UHFFFAOYSA-N

> <FORMULA>
C5H12NO4P

> <MOLECULAR_WEIGHT>
181.1268

> <EXACT_MASS>
181.050394389

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.142129413354006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid

> <ALOGPS_LOGP>
-2.48

> <JCHEM_LOGP>
-3.78245838674245

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.7331677269471717

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8575278318808435

> <JCHEM_PKA_STRONGEST_BASIC>
9.52908597803123

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
39.66100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
basta

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0290800 (basta)

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PDB for NP0290800 (basta)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.286   1.897   0.000  0.00  0.00           C+0
HETATM    2  P   UNK     0       4.620   2.667   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       5.390   1.334   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0290800 (basta)
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SMILES for NP0290800 (basta)
CP(O)(=O)CCC(N)C(O)=O
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INCHI for NP0290800 (basta)
InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
PhosphinothricinChEBI
2-Amino-4-(hydroxymethylphosphinyl)butanoic acidKegg
2-Amino-4-(hydroxymethylphosphinyl)butanoateGenerator
Glufosinic acidGenerator
Glufosinate-ammoniumMeSH
Phosphinothricin, monoammonium saltMeSH
Phosphinothricin, monosodium salt, (S)-isomerMeSH
Phosphinothricin hydrochloride, (S)-isomerMeSH
Phosphinothricin, sodium salt, (S)-isomerMeSH
Phosphinothricin, barium (1:1) salt, (+-)-isomerMeSH
Phosphinothricin, monoammonium salt, (S)-isomerMeSH
Phosphinothricin, copper (+2) saltMeSH
Phosphinothricin, disodium salt, (S)-isomerMeSH
Phosphinothricin, monosodium saltMeSH
Phosphinothricin, dipotassium salt, (S)-isomerMeSH
Glufosinate ammoniumMeSH
Phosphinothricin, disodium saltMeSH
BastaMeSH
Phosphinothricin, monopotassium salt, (S)-isomerMeSH
2-Amino-4-methylphosphinobutyric acidMeSH
Ammonium glufosinateMeSH
Ammonium-DL-homoalanine-4-yl(methyl)-phosphinateMeSH
DL-GlufosinateMeSH
Phosphinothricin hydrochlorideMeSH
Phosphinothricin, (S)-isomerMeSH
Phosphinothricin, calcium (2:1) salt, (S)-isomerMeSH
Glufosinate-pMeSH
Phosphinothricin, diammonium saltMeSH
3-amino-3-Carboxypropylmethylphosphinic acidChEBI
DL-2-amino-4-(methylphosphino)Butanoic acidChEBI
3-amino-3-CarboxypropylmethylphosphinateGenerator
DL-2-amino-4-(methylphosphino)ButanoateGenerator
Chemical FormulaC5H12NO4P
Average Mass181.1268 Da
Monoisotopic Mass181.05039 Da
IUPAC Name2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid
Traditional Namebasta
CAS Registry NumberNot Available
SMILES
CP(O)(=O)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H12NO4P/c1-11(9,10)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)(H,9,10)
InChI KeyIAJOBQBIJHVGMQ-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 hygroscopicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Fatty acid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Primary amine
    • 

  • Organophosphorus compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-2.5ALOGPS
logP-3.8ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.66 m³·mol⁻¹ChemAxon
Polarizability16.14 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 IDC00000797  
Chemspider IDNot Available
KEGG Compound IDC05042  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlufosinate  
METLIN IDNot Available
PubChem Compound4794  
PDB IDNot Available
ChEBI ID142851  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]