NP-MRD: Showing NP-Card for 2-(1-methylpyrrolidin-2-yl)benzoic acid (NP0177577)

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Record Information

Version

2.0

Created at

2022-09-03 15:26:07 UTC

Updated at

2022-09-03 15:26:08 UTC

NP-MRD ID

NP0177577

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(1-methylpyrrolidin-2-yl)benzoic acid

Description

2-(1-Methyl-pyrrolidin-2-yl)-benzoic acid belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 2-(1-methylpyrrolidin-2-yl)benzoic acid is found in Bessera tenuiflora and Rhoiptelea chiliantha. 2-(1-Methyl-pyrrolidin-2-yl)-benzoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.9957   -0.5941   -1.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.8196   -0.5483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0617   -1.4761    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7198   -0.8946    1.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4068    0.5785    1.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7369    0.3613    0.0506 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6465    0.7783    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9231    2.0904    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148    2.5618    0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2587    1.7383   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.4307   -0.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6921   -0.0470   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -1.4627   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3933   -2.0812    0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861   -2.1354   -1.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768    0.3820   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207   -0.7677   -2.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -1.3476   -1.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -2.5679    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1073   -1.1990    0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7931   -1.3795    2.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5831   -0.9698    2.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2724    1.2040    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6838    0.9224    2.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974    1.2131   -0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1327    2.7860    0.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    3.5794    0.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    2.1084   -0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444   -0.2767   -0.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -2.7155   -2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
  6  2  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  6
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 15 30  1  0
M  END


  Mrv1533004171521292D          

 15 16  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081   -2.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8235   -3.0814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -3.3785    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177577

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCCC1C1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO2/c1-13-8-4-7-11(13)9-5-2-3-6-10(9)12(14)15/h2-3,5-6,11H,4,7-8H2,1H3,(H,14,15)

> <INCHI_KEY>
PURIRTNUIAQQNH-UHFFFAOYSA-N

> <FORMULA>
C12H15NO2

> <MOLECULAR_WEIGHT>
205.257

> <EXACT_MASS>
205.110278727

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.30405376277314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(1-methylpyrrolidin-2-yl)benzoic acid

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
-0.6927993694647151

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1018596556679965

> <JCHEM_PKA_STRONGEST_BASIC>
9.153623877268112

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
59.06810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(1-methylpyrrolidin-2-yl)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.044  -2.739   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.829  -0.757   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.973  -1.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.653  -3.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.868  -5.276   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.404  -5.752   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.013  -6.307   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-(1-Methyl-pyrrolidin-2-yl)-benzoate	Generator
2-(1-Methylpyrrolidin-2-yl)benzoate	Generator

Chemical Formula

C₁₂H₁₅NO₂

Average Mass

205.2570 Da

Monoisotopic Mass

205.11028 Da

IUPAC Name

2-(1-methylpyrrolidin-2-yl)benzoic acid

Traditional Name

2-(1-methylpyrrolidin-2-yl)benzoic acid

CAS Registry Number

Not Available

SMILES

CN1CCCC1C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C12H15NO2/c1-13-8-4-7-11(13)9-5-2-3-6-10(9)12(14)15/h2-3,5-6,11H,4,7-8H2,1H3,(H,14,15)

InChI Key

PURIRTNUIAQQNH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bessera tenuiflora	LOTUS Database	35616633
Rhoiptelea chiliantha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Phenylpyrrolidines

Direct Parent

Phenylpyrrolidines

Alternative Parents

Substituents

2-phenylpyrrolidine
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Aralkylamine
Monocyclic benzene moiety
N-alkylpyrrolidine
Benzenoid
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Amino acid
Amino acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.01	ALOGPS
logP	-0.69	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.1	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.07 m³·mol⁻¹	ChemAxon
Polarizability	22.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53462701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(1-methylpyrrolidin-2-yl)benzoic acid (NP0177577)

MOL for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

3D MOL for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

3D SDF for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

3D-SDF for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

PDB for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

3D PDB for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

SMILES for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

INCHI for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

Structure for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)

3D Structure for NP0177577 (2-(1-methylpyrrolidin-2-yl)benzoic acid)