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Showing NP-Card for 3-azabicyclo[3.1.0]hexane-2-carboxylic acid (NP0246236)

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Record Information
Version2.0
Created at2022-09-07 07:37:55 UTC
Updated at2022-09-07 07:37:55 UTC
NP-MRD IDNP0246236
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-azabicyclo[3.1.0]hexane-2-carboxylic acid
Description3-Azabicyclo[3.1.0]Hexane-2-carboxylic acid belongs to the class of organic compounds known as bicyclic amino acids and derivatives. These are sugar amino acids in which the amino acid is attached to or partly borne within a bicyclic ring system. 3-azabicyclo[3.1.0]hexane-2-carboxylic acid is found in Aesculus parviflora and Ephedra foliata. 3-Azabicyclo[3.1.0]Hexane-2-carboxylic acid is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)


  Mrv1533004171504182D          

  9 10  0  0  0  0            999 V2000
    1.9454    2.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    2.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   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  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
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.5022   -1.4002   -0.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -0.4344   -0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360    0.6197    0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126   -0.3968    0.3302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0615   -1.5357   -0.0802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538   -1.1075   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3975    0.3429   -0.4130 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1234    1.3036    0.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.8398   -0.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9917    1.3728   -0.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7023   -0.3720    1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940   -1.7776   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8363   -1.1861    0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421   -1.6735   -0.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982    0.7280   -1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6243    2.2672    0.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599    0.8733    1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4976    1.5365   -0.8068 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  4  1  0
  9  7  1  0
  3 10  1  0
  4 11  1  1
  5 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  6
  8 16  1  0
  8 17  1  0
  9 18  1  6
M  END
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3D SDF for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)


  Mrv1533004171504182D          

  9 10  0  0  0  0            999 V2000
    1.9454    2.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975    2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    2.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275    0.8862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434    0.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    1.2987    0.0000 C   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  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
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1NCC2CC12

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO2/c8-6(9)5-4-1-3(4)2-7-5/h3-5,7H,1-2H2,(H,8,9)

> <INCHI_KEY>
JBDOTWVUXVXVDR-UHFFFAOYSA-N

> <FORMULA>
C6H9NO2

> <MOLECULAR_WEIGHT>
127.143

> <EXACT_MASS>
127.063328534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.551061561287838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-azabicyclo[3.1.0]hexane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.63

> <JCHEM_LOGP>
-2.746990686148826

> <ALOGPS_LOGS>
-0.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7819158195568812

> <JCHEM_PKA_STRONGEST_BASIC>
11.18543425521192

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
30.6043

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-azabicyclo[3.1.0]hexane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)

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PDB for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       3.631   5.509   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.662   4.365   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.168   4.685   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.186   2.900   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.091   1.654   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.186   0.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.388   1.654   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4    7                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END

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3D PDB for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)
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SMILES for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)
OC(=O)C1NCC2CC12
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INCHI for NP0246236 (3-azabicyclo[3.1.0]hexane-2-carboxylic acid)
InChI=1S/C6H9NO2/c8-6(9)5-4-1-3(4)2-7-5/h3-5,7H,1-2H2,(H,8,9)
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Synonyms
ValueSource
3-Azabicyclo[3.1.0]hexane-2-carboxylateGenerator
Chemical FormulaC6H9NO2
Average Mass127.1430 Da
Monoisotopic Mass127.06333 Da
IUPAC Name3-azabicyclo[3.1.0]hexane-2-carboxylic acid
Traditional Name3-azabicyclo[3.1.0]hexane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1NCC2CC12
InChI Identifier
InChI=1S/C6H9NO2/c8-6(9)5-4-1-3(4)2-7-5/h3-5,7H,1-2H2,(H,8,9)
InChI KeyJBDOTWVUXVXVDR-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
Aesculus parvifloraLOTUS Database
Ephedra foliataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic amino acids and derivatives. These are sugar amino acids in which the amino acid is attached to or partly borne within a bicyclic ring system.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentBicyclic amino acids and derivatives  
Alternative Parents
Substituents
  • Bicyclic amino acid
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Piperidinecarboxylic acid
    • 

  • Pyrrolidine carboxylic acid
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • Piperidine
    • 

  • Pyrrolidine
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • 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-2.6ALOGPS
logP-2.7ChemAxon
logS-0.05ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)11.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.6 m³·mol⁻¹ChemAxon
Polarizability12.55 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]