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Showing NP-Card for 4-oxa-1-azabicyclo[3.2.0]heptan-7-one (NP0216498)

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Record Information
Version2.0
Created at2022-09-05 16:29:37 UTC
Updated at2022-09-05 16:29:38 UTC
NP-MRD IDNP0216498
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-oxa-1-azabicyclo[3.2.0]heptan-7-one
Description4-Oxa-1-azabicyclo[3.2.0]Heptan-7-one, also known as 4-oabch-7-one, belongs to the class of organic compounds known as clavams. These are organic compounds containing a 4-oxa-1-azabicyclo[3.2.0]Heptan-7-one moiety. Clavams are similar to penams, but with an oxygen substituted for the sulfur in the penam skeleton. 4-oxa-1-azabicyclo[3.2.0]heptan-7-one is found in Streptomyces clavuligerus. 4-oxa-1-azabicyclo[3.2.0]heptan-7-one was first documented in 2003 (PMID: 14529451). Based on a literature review very few articles have been published on 4-oxa-1-azabicyclo[3.2.0]Heptan-7-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)


  Mrv1652309052218292D          

  8  9  0  0  0  0            999 V2000
    0.3649   -1.1595    0.0000 O   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    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    0.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  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
  2  8  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
Download

3D MOL for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)

     RDKit          3D

 15 16  0  0  0  0  0  0  0  0999 V2000
   -2.4095    1.5271    1.0083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661    0.6546    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7227   -0.5754   -0.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4007   -0.0361   -0.8343 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6321   -0.9536   -0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -0.3871   -0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    0.3740    0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2666    0.4641    0.5512 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5400   -0.5806   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5634   -1.5238    0.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507    0.7578   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3182   -1.2151    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3109    0.2762   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6112    1.3726    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.1545    1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  2  1  0
  8  4  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  6
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)


  Mrv1652309052218292D          

  8  9  0  0  0  0            999 V2000
    0.3649   -1.1595    0.0000 O   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    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733    0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579    0.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -0.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -0.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.5762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  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
  2  8  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CC2OCCN12

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO2/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2

> <INCHI_KEY>
UBIRCWMYTXDXJX-UHFFFAOYSA-N

> <FORMULA>
C5H7NO2

> <MOLECULAR_WEIGHT>
113.116

> <EXACT_MASS>
113.047678469

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.921782678748396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-oxa-1-azabicyclo[3.2.0]heptan-7-one

> <JCHEM_LOGP>
-0.537216819

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.724170907767615

> <JCHEM_PKA_STRONGEST_BASIC>
-4.087901652579348

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
26.2117

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-oxa-1-azabicyclo[3.2.0]heptan-7-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)

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PDB for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       0.681  -2.164   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.770  -1.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.770   0.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.310   0.464   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.775   0.940   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.680  -0.306   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.775  -1.551   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.310  -1.076   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2    4                                                  
MASTER        0    0    0    0    0    0    0    0    8    0   18    0
END

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3D PDB for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)
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SMILES for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)
O=C1CC2OCCN12
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INCHI for NP0216498 (4-oxa-1-azabicyclo[3.2.0]heptan-7-one)
InChI=1S/C5H7NO2/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2
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Synonyms
ValueSource
4-OABCH-7-oneMeSH
4-Oxa-1-azabicyclo(3.2.0)heptan-7-oneMeSH
Chemical FormulaC5H7NO2
Average Mass113.1160 Da
Monoisotopic Mass113.04768 Da
IUPAC Name4-oxa-1-azabicyclo[3.2.0]heptan-7-one
Traditional Name4-oxa-1-azabicyclo[3.2.0]heptan-7-one
CAS Registry NumberNot Available
SMILES
O=C1CC2OCCN12
InChI Identifier
InChI=1S/C5H7NO2/c7-4-3-5-6(4)1-2-8-5/h5H,1-3H2
InChI KeyUBIRCWMYTXDXJX-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 clavuligerusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as clavams. These are organic compounds containing a 4-oxa-1-azabicyclo[3.2.0]Heptan-7-one moiety. Clavams are similar to penams, but with an oxygen substituted for the sulfur in the penam skeleton.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactams  
Sub ClassBeta lactams  
Direct ParentClavams  
Alternative Parents
Substituents
  • Clavam
    • 

  • Para-oxazepine
    • 

  • Oxazolidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Azetidine
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP-0.54ChemAxon
pKa (Strongest Acidic)18.72ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.21 m³·mol⁻¹ChemAxon
Polarizability10.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID168494  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound194189  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Singh R, Micetich RG: 4-oxa-1-azabicyclo[3.2.0]heptan-7-one derivatives as anti-tumor agents. Curr Med Chem Anticancer Agents. 2003 Nov;3(6):431-8. doi:  10.2174/1568011033482233. [PubMed:14529451  ] 
  2. LOTUS database [Link]