Pyrrolidin-3-yl-acetic acid ((R)-(-)-Homo beta Proline)

ID: ALA1788265

Chembl Id: CHEMBL1788265

Cas Number: 122442-01-7

PubChem CID: 1502074

Max Phase: Preclinical

Molecular Formula: C6H11NO2

Molecular Weight: 129.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@H]1CCNC1

Standard InChI:  InChI=1S/C6H11NO2/c8-6(9)3-5-1-2-7-4-5/h5,7H,1-4H2,(H,8,9)/t5-/m1/s1

Standard InChI Key:  OUENRUZPZZFMCA-RXMQYKEDSA-N

Alternative Forms

1. Parent:

   

   ALA1788265

   (R)-3-Pyrrolidineacetic acid

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: 129.16

Molecular Weight (Monoisotopic): 129.0790

AlogP: 0.07

#Rotatable Bonds: 2

Polar Surface Area: 49.33

Molecular Species: ZWITTERION

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.41

CX Basic pKa: 11.49

CX LogP: -2.77

CX LogD: -2.77

Aromatic Rings: ┄

Heavy Atoms: 9

QED Weighted: 0.55

Np Likeness Score: 0.52

References

1. Nielsen L, Brehm L, Krogsgaard-Larsen P..  (1990)  GABA agonists and uptake inhibitors. Synthesis, absolute stereochemistry, and enantioselectivity of (R)-(-)- and (S)-(+)-homo-beta-proline.,  33  (1): [PMID:2153214] [10.1021/jm00163a012]

2. Giraudo A, Krall J, Bavo F, Nielsen B, Kongstad KT, Rolando B, De Blasio R, Gloriam DE, Löffler R, Thiesen L, Harpsøe K, Frydenvang K, Boschi D, Wellendorph P, Lolli ML, Jensen AA, Frølund B..  (2019)  Five-Membered N-Heterocyclic Scaffolds as Novel Amino Bioisosteres at γ-Aminobutyric Acid (GABA) Type A Receptors and GABA Transporters.,  62  (12): [PMID:31117514] [10.1021/acs.jmedchem.9b00026]

Source

Source(1):

• Scientific Literature