2-Carboxy-1,1-dimethyl-pyrrolidinium chloride

ID: ALA166795

Cas Number: 4136-37-2

PubChem CID: 17751044

Max Phase: Preclinical

Molecular Formula: C7H14ClNO2

Molecular Weight: 143.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Stachydrine HCl | Stachydrine hydrochloride|4136-37-2|Stachydrine HCl|(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate;hydrochloride|CHEMBL166795|SCHEMBL1340043|DTXSID00961642|HMS1569N06|MFCD21609192|AKOS037514849|CCG-208449|Stachydrine (hydrochloride) (471-87-4 free base)|(2S)-2-carboxy-1,1-dimethyl-pyrrolidinium,innersalt,monohydrochloride|1,1-Dimethylpyrrolidin-1-ium-2-carboxylate--hydrogen chloride (1/1)

Canonical SMILES:  C[N+]1(C)CCC[C@H]1C(=O)[O-].Cl

Standard InChI:  InChI=1S/C7H13NO2.ClH/c1-8(2)5-3-4-6(8)7(9)10;/h6H,3-5H2,1-2H3;1H/t6-;/m0./s1

Standard InChI Key:  DUNMULOWUUIQIL-RGMNGODLSA-N

Molfile:  

     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
   13.8782  -11.0831    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7577   -8.6373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8463   -9.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0908   -9.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5358   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9507   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5593   -9.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5593  -10.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2722   -9.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8463   -7.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5835   -8.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  6  1  0
  7  8  2  0
  7  9  1  0
  3  7  1  6
  2 10  1  0
  2 11  1  0
M  CHG  2   2   1   9  -1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 143.19

Molecular Weight (Monoisotopic): 143.0946

AlogP: -1.02

#Rotatable Bonds: 1

Polar Surface Area: 40.13

Molecular Species: ACID

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.26

CX Basic pKa: ┄

CX LogP: -3.88

CX LogD: -3.11

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.44

Np Likeness Score: 1.35

References

1. Woster PM, Murray WJ..  (1986)  Synthesis and biological evaluation of cyclic analogues of 1-carnitine as potential agents in the treatment of myocardial ischemia.,  29  (5): [PMID:3084787] [10.1021/jm00155a045]

2. Huss U, Ringbom T, Perera P, Bohlin L, Vasänge M..  (2002)  Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.,  65  (11): [PMID:12444669] [10.1021/np020023m]

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

Source

Source(1):

• Scientific Literature