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Showing NP-Card for L-4-Methylene-2-pyrrolidinecarboxylic acid (NP0045366)

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Record Information
Version2.0
Created at2022-03-17 19:18:42 UTC
Updated at2022-03-17 19:18:42 UTC
NP-MRD IDNP0045366
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-4-Methylene-2-pyrrolidinecarboxylic acid
Description(±)-4-Methylene-2-pyrrolidinecarboxylic acid, also known as 4-methylene-L-proline, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (±)-4-Methylene-2-pyrrolidinecarboxylic acid is a very strong basic compound (based on its pKa). Outside of the human body, (±)-4-Methylene-2-pyrrolidinecarboxylic acid has been detected, but not quantified in, fruits. This could make (±)-4-methylene-2-pyrrolidinecarboxylic acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)


  Mrv0541 02241207582D          

  9  9  0  0  0  0            999 V2000
   -0.9484    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233    0.7421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -0.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.2832    0.5575    1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -0.0135    0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518   -0.9328   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0449   -0.7611   -1.1073 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524    0.2431   -0.3769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2081    0.0606   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -0.8979   -0.9592 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904    0.9770    0.3107 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.1121    1.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3055    0.3807    0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2461    1.2359    2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -1.9829   -0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0921   -0.7311   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.6544   -1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4367    1.2711   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823    1.9611    0.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.0056    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -0.8311    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  9  1  0
  9  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  8 16  1  0
  5 15  1  6
  9 17  1  0
  9 18  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
M  END
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3D SDF for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)


  Mrv0541 02241207582D          

  9  9  0  0  0  0            999 V2000
   -0.9484    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233    0.7421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084    0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -0.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC(=C)CN1

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)

> <INCHI_KEY>
PEYQZZMUNYLHII-UHFFFAOYSA-N

> <FORMULA>
C6H9NO2

> <MOLECULAR_WEIGHT>
127.1412

> <EXACT_MASS>
127.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
12.688946378896896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylidenepyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.22

> <JCHEM_LOGP>
-2.4732942640513387

> <ALOGPS_LOGS>
0.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9614290941020185

> <JCHEM_PKA_STRONGEST_BASIC>
10.48199967963638

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
32.2364

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylidenepyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)

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PDB for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)
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      -1.770   0.923   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.230   1.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.692   0.153   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.230  -1.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.770  -0.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.002  -1.539   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.002   1.539   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.232   0.153   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.002  -1.231   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    3    7    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)
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SMILES for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)
OC(=O)C1CC(=C)CN1
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INCHI for NP0045366 (L-4-Methylene-2-pyrrolidinecarboxylic acid)
InChI=1S/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
(±)-4-methylene-2-pyrrolidinecarboxylateGenerator
4-Methyleneproline, (DL)-isomerHMDB
4-Methylene-L-prolineHMDB
4-Methylidenepyrrolidine-2-carboxylateGenerator
4-MethyleneprolineMeSH
Chemical FormulaC6H9NO2
Average Mass127.1412 Da
Monoisotopic Mass127.06333 Da
IUPAC Name4-methylidenepyrrolidine-2-carboxylic acid
Traditional Name4-methylidenepyrrolidine-2-carboxylic acid
CAS Registry Number20309-87-9
SMILES
OC(=O)C1CC(=C)CN1
InChI Identifier
InChI=1S/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)
InChI KeyPEYQZZMUNYLHII-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arachis hypogaeaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentProline and derivatives  
Alternative Parents
Substituents
  • Proline or derivatives
    • 

  • Alpha-amino acid
    • 

  • Pyrrolidine carboxylic acid
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • Pyrrolidine
    • 

  • Amino acid
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary aliphatic amine
    • 

  • Carboxylic acid
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic nitrogen 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-2.2ALOGPS
logP-2.5ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)10.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.24 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029434  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000538  
KNApSAcK IDNot Available
Chemspider ID485385  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound558375  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available