(3S,4aR,6S,8aR)-6-(((S)-2-carboxy-4,4-difluoropyrrolidin-1-yl)methyl)decahydroisoquinoline-3-carboxylic acid

ID: ALA1234118

Chembl Id: CHEMBL1234118

Cas Number: 317844-33-0

PubChem CID: 9935648

Max Phase: Preclinical

Molecular Formula: C16H24F2N2O4

Molecular Weight: 346.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1C[C@H]2C[C@@H](CN3CC(F)(F)C[C@H]3C(=O)O)CC[C@H]2CN1

Standard InChI:  InChI=1S/C16H24F2N2O4/c17-16(18)5-13(15(23)24)20(8-16)7-9-1-2-10-6-19-12(14(21)22)4-11(10)3-9/h9-13,19H,1-8H2,(H,21,22)(H,23,24)/t9-,10-,11+,12-,13-/m0/s1

Standard InChI Key:  OXQXJYQSWZFDBB-WJTVCTBASA-N

Alternative Forms

1. Parent:

   

   ALA1234118

   3-Isoquinolinecarboxylic acid, 6-(((2S)-2-carboxy-4,4-difluoro-1-pyrrolidinyl)methyl)decahydro-, (3S,4aR,6S,8aR)-

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: 346.37

Molecular Weight (Monoisotopic): 346.1704

AlogP: 1.26

#Rotatable Bonds: 4

Polar Surface Area: 89.87

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.59

CX Basic pKa: 10.55

CX LogP: -2.54

CX LogD: -3.70

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.71

Np Likeness Score: 0.75

References

1. Szymańska E, Chałupnik P, Szczepańska K, Cuñado Moral AM, Pickering DS, Nielsen B, Johansen TN, Kieć-Kononowicz K..  (2016)  Design, synthesis and structure-activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands.,  26  (22): [PMID:27765511] [10.1016/j.bmcl.2016.09.075]

2. Krogsgaard-Larsen N, Delgar CG, Koch K, Brown PM, Møller C, Han L, Huynh TH, Hansen SW, Nielsen B, Bowie D, Pickering DS, Kastrup JS, Frydenvang K, Bunch L..  (2017)  Design and Synthesis of a Series of l-trans-4-Substituted Prolines as Selective Antagonists for the Ionotropic Glutamate Receptors Including Functional and X-ray Crystallographic Studies of New Subtype Selective Kainic Acid Receptor Subtype 1 (GluK1) Antagonist (2S,4R)-4-(2-Carboxyphenoxy)pyrrolidine-2-carboxylic Acid.,  60  (1): [PMID:28005385] [10.1021/acs.jmedchem.6b01516]

Source

Source(1):

• Scientific Literature