((3S,4S)-N-[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopentyl]-3-methoxytetrahydro-2H-pyran-4-amine

ID: ALA1683074

Chembl Id: CHEMBL1683074

Cas Number: 1310796-72-5

PubChem CID: 50992246

Max Phase: Preclinical

Molecular Formula: C25H37F3N4O3

Molecular Weight: 498.59

Molecule Type: Small molecule

Names and Identifiers

Synonyms: PF-903 | CHEMBL1683074|1310796-72-5|((1S,3R)-1-Isopropyl-3-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)cyclopentyl)(4-(4-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)methanone|starbld0044618|W6SXW7SQ3F|INCB10820|INCB-10820|BDBM50337619|PF-903|PF-4178903|((1S,3R)-1-isopropyl-3-((3S,4S)-3-methoxytetrahydro-2H-pyran-4-ylamino)cyclopentyl)(4-(4-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)methanone|((3S,4S)-N-[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cShow More⌵

Canonical SMILES:  CO[C@@H]1COCC[C@@H]1N[C@@H]1CC[C@@](C(=O)N2CCN(c3cc(C(F)(F)F)ccn3)CC2)(C(C)C)C1

Standard InChI:  InChI=1S/C25H37F3N4O3/c1-17(2)24(7-4-19(15-24)30-20-6-13-35-16-21(20)34-3)23(33)32-11-9-31(10-12-32)22-14-18(5-8-29-22)25(26,27)28/h5,8,14,17,19-21,30H,4,6-7,9-13,15-16H2,1-3H3/t19-,20+,21-,24+/m1/s1

Standard InChI Key:  DQWSENNLMPJNRJ-WHLIWEHUSA-N

Alternative Forms

1. Parent:

   

   ALA1683074

   ((1S,3R)-1-Isopropyl-3-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)cyclopentyl)(4-(4-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)methanone

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: 498.59

Molecular Weight (Monoisotopic): 498.2818

AlogP: 3.34

#Rotatable Bonds: 6

Polar Surface Area: 66.93

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.98

CX LogP: 3.22

CX LogD: 0.70

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.65

Np Likeness Score: -0.65

References

1. Zheng C, Cao G, Xia M, Feng H, Glenn J, Anand R, Zhang K, Huang T, Wang A, Kong L, Li M, Galya L, Hughes RO, Devraj R, Morton PA, Rogier DJ, Covington M, Baribaud F, Shin N, Scherle P, Diamond S, Yeleswaram S, Vaddi K, Newton R, Hollis G, Friedman S, Metcalf B, Xue CB..  (2011)  Discovery of INCB10820/PF-4178903, a potent, selective, and orally bioavailable dual CCR2 and CCR5 antagonist.,  21  (5): [PMID:21295478] [10.1016/j.bmcl.2011.01.015]

2. Trujillo JI, Huang W, Hughes RO, Rogier DJ, Turner SR, Devraj R, Morton PA, Xue CB, Chao G, Covington MB, Newton RC, Metcalf B..  (2011)  Design and synthesis of novel CCR2 antagonists: investigation of non-aryl/heteroaryl binding motifs.,  21  (6): [PMID:21316220] [10.1016/j.bmcl.2011.01.052]

3. Hughes RO, Rogier DJ, Devraj R, Zheng C, Cao G, Feng H, Xia M, Anand R, Xing L, Glenn J, Zhang K, Covington M, Morton PA, Hutzler JM, Davis JW, Scherle P, Baribaud F, Bahinski A, Mo ZL, Newton R, Metcalf B, Xue CB..  (2011)  Discovery of ((1S,3R)-1-isopropyl-3-((3S,4S)-3-methoxy-tetrahydro-2H-pyran-4-ylamino)cyclopentyl)(4-(5-(trifluoromethyl)pyridazin-3-yl)piperazin-1-yl)methanone, PF-4254196, a CCR2 antagonist with an improved cardiovascular profile.,  21  (9): [PMID:21315584] [10.1016/j.bmcl.2011.01.034]

Source

Source(1):

• Scientific Literature