(S)-1-(2-Amino-2-cyclohexyl-acetyl)-pyrrolidine-2-carbonitrile

ID: ALA307636

Chembl Id: CHEMBL307636

PubChem CID: 11075394

Max Phase: Preclinical

Molecular Formula: C13H21N3O

Molecular Weight: 235.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cyclohexylglycine-(2S)-Cyanopyrrolidine | Chg-Pro-CN|cyclohexylglycine-(2S)-cyanopyrrolidine|CHEMBL307636|BMCL15687 Compound 3|SCHEMBL14392566|BDBM11694|Cyclohexylglycine-(2S)-cyanopyrolidine 3|Cyclohexylglycine-(2S)-cyanopyrrolidine 2|(2S)-1-[(2S)-2-amino-2-cyclohexylacetyl]pyrrolidine-2-carbonitrile

Canonical SMILES:  N#C[C@@H]1CCCN1C(=O)[C@@H](N)C1CCCCC1

Standard InChI:  InChI=1S/C13H21N3O/c14-9-11-7-4-8-16(11)13(17)12(15)10-5-2-1-3-6-10/h10-12H,1-8,15H2/t11-,12-/m0/s1

Standard InChI Key:  SXNUNNAPZNTPQV-RYUDHWBXSA-N

Alternative Forms

1. Parent:

   

   ALA307636

   cyclohexylglycine-(2S)-cyanopyrrolidine

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: 235.33

Molecular Weight (Monoisotopic): 235.1685

AlogP: 1.41

#Rotatable Bonds: 2

Polar Surface Area: 70.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.49

CX LogP: 0.97

CX LogD: -0.15

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.79

Np Likeness Score: -0.11

References

1. Ashworth DM, Atrash B, Baker GR, Baxter AJ, Jenkins PD, Jones D, Szelke M.  (1996)  2-cyanopyrrolidides as potent, stable inhibitors of dipeptidyl peptidase IV,  6  (10): [10.1016/0960-894X(96)00190-4]

2. Villhauer EB, Brinkman JA, Naderi GB, Dunning BE, Mangold BL, Mone MD, Russell ME, Weldon SC, Hughes TE..  (2002)  1-[2-[(5-Cyanopyridin-2-yl)amino]ethylamino]acetyl-2-(S)-pyrrolidinecarbonitrile: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties.,  45  (12): [PMID:12036346] [10.1021/jm025522z]

3. Villhauer EB, Brinkman JA, Naderi GB, Burkey BF, Dunning BE, Prasad K, Mangold BL, Russell ME, Hughes TE..  (2003)  1-[[(3-hydroxy-1-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine: a potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitor with antihyperglycemic properties.,  46  (13): [PMID:12801240] [10.1021/jm030091l]

4. Jiaang WT, Chen YS, Hsu T, Wu SH, Chien CH, Chang CN, Chang SP, Lee SJ, Chen X..  (2005)  Novel isoindoline compounds for potent and selective inhibition of prolyl dipeptidase DPP8.,  15  (3): [PMID:15664838] [10.1016/j.bmcl.2004.11.023]

5. Ferraris D, Ko YS, Calvin D, Chiou T, Lautar S, Thomas B, Wozniak K, Rojas C, Kalish V, Belyakov S..  (2004)  Ketopyrrolidines and ketoazetidines as potent dipeptidyl peptidase IV (DPP IV) inhibitors.,  14  (22): [PMID:15482928] [10.1016/j.bmcl.2004.08.057]

6. Lu IL, Lee SJ, Tsu H, Wu SY, Kao KH, Chien CH, Chang YY, Chen YS, Cheng JH, Chang CN, Chen TW, Chang SP, Chen X, Jiaang WT..  (2005)  Glutamic acid analogues as potent dipeptidyl peptidase IV and 8 inhibitors.,  15  (13): [PMID:15927466] [10.1016/j.bmcl.2005.04.051]

7. Tsu H, Chen X, Chen CT, Lee SJ, Chang CN, Kao KH, Coumar MS, Yeh YT, Chien CH, Wang HS, Lin KT, Chang YY, Wu SH, Chen YS, Lu IL, Wu SY, Tsai TY, Chen WC, Hsieh HP, Chao YS, Jiaang WT..  (2006)  2-[3-[2-[(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethylamino]-3-methyl-1-oxobutyl]- 1,2,3,4-tetrahydroisoquinoline: a potent, selective, and orally bioavailable dipeptide-derived inhibitor of dipeptidyl peptidase IV.,  49  (1): [PMID:16392822] [10.1021/jm0507781]

8. Havale SH, Pal M..  (2009)  Medicinal chemistry approaches to the inhibition of dipeptidyl peptidase-4 for the treatment of type 2 diabetes.,  17  (5): [PMID:19217790] [10.1016/j.bmc.2009.01.061]

Source

Source(1):

• Scientific Literature