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Showing NP-Card for carbapenem-3-carboxylic acid (NP0192152)

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Record Information
Version2.0
Created at2022-09-04 09:17:50 UTC
Updated at2022-09-04 09:17:50 UTC
NP-MRD IDNP0192152
Secondary Accession NumbersNone
Natural Product Identification
Common Namecarbapenem-3-carboxylic acid
Description7-Oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid. carbapenem-3-carboxylic acid is found in Pectobacterium carotovorum. 7-Oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0192152 (carbapenem-3-carboxylic acid)


  Mrv0541 04121513252D          

 11 12  0  0  0  0            999 V2000
    3.6198    2.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    2.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    3.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    0.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3649    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    1.4012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0192152 (carbapenem-3-carboxylic acid)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.3718   -1.2316   -1.7274 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016   -0.1960   -1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    0.6417   -0.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9438    0.1093   -0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432    1.2004    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6540    1.2156    0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3234    0.2233   -0.0202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9100   -1.0101    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.6907   -0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707   -2.7104   -1.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2277   -0.6729   -0.4125 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582    0.7408   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4396    1.9969    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048    0.9153    1.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    2.2113    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927    0.6541   -0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -1.2930    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0116   -1.1038    0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  4  1  0
 11  7  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
  7 16  1  6
  8 17  1  0
  8 18  1  0
M  END
Download

3D SDF for NP0192152 (carbapenem-3-carboxylic acid)


  Mrv0541 04121513252D          

 11 12  0  0  0  0            999 V2000
    3.6198    2.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    2.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608    3.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    0.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    0.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9483    1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3649    1.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    1.4012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0192152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CCC2CC(=O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO3/c9-6-3-4-1-2-5(7(10)11)8(4)6/h2,4H,1,3H2,(H,10,11)

> <INCHI_KEY>
BSIMZHVOQZIAOY-UHFFFAOYSA-N

> <FORMULA>
C7H7NO3

> <MOLECULAR_WEIGHT>
153.137

> <EXACT_MASS>
153.042593089

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.25654472955749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
-0.6691576903333334

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8465217598944945

> <JCHEM_PKA_STRONGEST_BASIC>
-8.246762933722971

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
37.0092

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0192152 (carbapenem-3-carboxylic acid)

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PDB for NP0192152 (carbapenem-3-carboxylic acid)
HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  O   UNK     0       6.757   4.876   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.251   4.556   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.220   5.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.775   3.091   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.680   1.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.775   0.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.310   1.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.770   1.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.770   2.616   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.681   3.704   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.310   2.616   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0192152 (carbapenem-3-carboxylic acid)
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SMILES for NP0192152 (carbapenem-3-carboxylic acid)
OC(=O)C1=CCC2CC(=O)N12
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INCHI for NP0192152 (carbapenem-3-carboxylic acid)
InChI=1S/C7H7NO3/c9-6-3-4-1-2-5(7(10)11)8(4)6/h2,4H,1,3H2,(H,10,11)
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View in JSmol
Synonyms
ValueSource
7-oxo-1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator
Carbapenem-3-carboxylic acidMeSH
Chemical FormulaC7H7NO3
Average Mass153.1370 Da
Monoisotopic Mass153.04259 Da
IUPAC Name7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Name7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CCC2CC(=O)N12
InChI Identifier
InChI=1S/C7H7NO3/c9-6-3-4-1-2-5(7(10)11)8(4)6/h2,4H,1,3H2,(H,10,11)
InChI KeyBSIMZHVOQZIAOY-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
Erwinia carotovoraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactams  
Sub ClassBeta lactams  
Direct ParentCarbapenems  
Alternative Parents
Substituents
  • Carbapenem
    • 

  • Alpha-amino acid or derivatives
    • 

  • Pyrroline carboxylic acid or derivatives
    • 

  • Pyrroline carboxylic acid
    • 

  • Azepine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Pyrroline
    • 

  • Azetidine
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP0.41ALOGPS
logP-0.67ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.01 m³·mol⁻¹ChemAxon
Polarizability14.26 ųChemAxon
Number of Rings2ChemAxon
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 Compound134085  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]