ID: ALA391466

Max Phase: Preclinical

Molecular Formula: C18H25N5O3S

Molecular Weight: 391.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C([C@@H]1C[C@H](N2CCN(c3ccc([N+](=O)[O-])cc3)CC2)CN1)N1CCSC1

Standard InChI:  InChI=1S/C18H25N5O3S/c24-18(22-9-10-27-13-22)17-11-16(12-19-17)21-7-5-20(6-8-21)14-1-3-15(4-2-14)23(25)26/h1-4,16-17,19H,5-13H2/t16-,17-/m0/s1

Standard InChI Key:  ZHJLERMYNKCYGH-IRXDYDNUSA-N

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

Properties

Molecular Weight: 391.50

Molecular Weight (Monoisotopic): 391.1678

AlogP: 0.98

#Rotatable Bonds: 4

Polar Surface Area: 81.96

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.38

CX LogP: 1.05

CX LogD: -0.91

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -1.37

References

1. Yoshida T, Sakashita H, Akahoshi F, Hayashi Y..  (2007)  [(S)-gamma-(4-Aryl-1-piperazinyl)-l-prolyl]thiazolidines as a novel series of highly potent and long-lasting DPP-IV inhibitors.,  17  (9): [PMID:17317162] [10.1016/j.bmcl.2007.01.110]

2. Yoshida T, Akahoshi F, Sakashita H, Sonda S, Takeuchi M, Tanaka Y, Nabeno M, Kishida H, Miyaguchi I, Hayashi Y..  (2012)  Fused bicyclic heteroarylpiperazine-substituted L-prolylthiazolidines as highly potent DPP-4 inhibitors lacking the electrophilic nitrile group.,  20  (16): [PMID:22824762] [10.1016/j.bmc.2012.06.033]

3. Yoshida T, Akahoshi F, Sakashita H, Kitajima H, Nakamura M, Sonda S, Takeuchi M, Tanaka Y, Ueda N, Sekiguchi S, Ishige T, Shima K, Nabeno M, Abe Y, Anabuki J, Soejima A, Yoshida K, Takashina Y, Ishii S, Kiuchi S, Fukuda S, Tsutsumiuchi R, Kosaka K, Murozono T, Nakamaru Y, Utsumi H, Masutomi N, Kishida H, Miyaguchi I, Hayashi Y..  (2012)  Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine): a highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes.,  20  (19): [PMID:22959556] [10.1016/j.bmc.2012.08.012]

Source

Source(1):

• Scientific Literature