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endo-1-(4-chlorophenyl)-N-((R)-3-(4-chlorophenyl)-1-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)-1-oxopropan-2-yl)cyclopropanecarboxamide ID: ALA1774022
PubChem CID: 54587189
Max Phase: Preclinical
Molecular Formula: C27H31Cl2N3O2
Molecular Weight: 500.47
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: CN1[C@@H]2CC[C@H]1C[C@@H](NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)C1(c3ccc(Cl)cc3)CC1)C2
Standard InChI: InChI=1S/C27H31Cl2N3O2/c1-32-22-10-11-23(32)16-21(15-22)30-25(33)24(14-17-2-6-19(28)7-3-17)31-26(34)27(12-13-27)18-4-8-20(29)9-5-18/h2-9,21-24H,10-16H2,1H3,(H,30,33)(H,31,34)/t21-,22+,23-,24-/m1/s1
Standard InChI Key: YHMAMSIULQZZNV-UEQSERJNSA-N
Molfile:
RDKit 2D
36 40 0 0 0 0 0 0 0 0999 V2000
-0.9007 -22.2663 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.1856 -22.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5282 -22.2640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5269 -21.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.2433 -22.6754 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.9572 -22.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7486 -21.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2961 -20.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4934 -20.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4580 -22.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6722 -22.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9018 -21.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7042 -21.7083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.8000 -20.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6145 -22.6799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3297 -22.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6133 -23.5049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.0435 -22.6821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7544 -22.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4678 -22.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4669 -23.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7468 -23.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0364 -23.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2597 -20.1248 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
4.0243 -23.0971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0
-0.1843 -23.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5308 -23.9140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5277 -24.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2420 -25.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9568 -24.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9528 -23.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2380 -23.4994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6724 -25.1466 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-5.1802 -23.9206 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-2.7500 -21.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9250 -21.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6 5 1 6
16 18 1 0
7 8 1 0
18 19 2 0
8 9 1 0
19 20 1 0
7 10 1 0
20 21 2 0
11 6 1 0
21 22 1 0
6 12 1 0
22 23 2 0
23 18 1 0
12 9 1 0
9 24 1 1
10 11 1 0
10 25 1 1
1 2 1 0
2 26 1 1
9 13 1 0
26 27 1 0
10 13 1 0
27 28 2 0
3 4 2 0
28 29 1 0
13 14 1 0
29 30 2 0
30 31 1 0
1 15 1 0
31 32 2 0
32 27 1 0
3 5 1 0
30 33 1 0
15 16 1 0
21 34 1 0
2 3 1 0
16 35 1 0
16 36 1 0
15 17 2 0
35 36 1 0
M END Associated Targets(Human) Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 500.47Molecular Weight (Monoisotopic): 499.1793AlogP: 4.49#Rotatable Bonds: 7Polar Surface Area: 61.44Molecular Species: BASEHBA: 3HBD: 2#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski): 1CX Acidic pKa: 12.21CX Basic pKa: 9.24CX LogP: 4.54CX LogD: 2.70Aromatic Rings: 2Heavy Atoms: 34QED Weighted: 0.59Np Likeness Score: -0.55
References 1. Napier S, Wishart G, Arbuckle W, Baker J, Barn D, Bingham M, Brown A, Byford A, Claxton C, Craighead M, Buchanan K, Fielding L, Gibson L, Goodwin R, Goutcher S, Irving N, MacSweeney C, Milne R, Mort C, Presland J, Sloan H, Thomson F, Turnbull Z, Young T.. (2011) The discovery of novel 8-azabicyclo[3.2.1]octan-3-yl)-3-(4-chlorophenyl) propanamides as vasopressin V1A receptor antagonists., 21 (10): [PMID:21458261 ] [10.1016/j.bmcl.2011.02.096 ]