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(1S,2R)-N-hydroxy-2-((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-2-(4-((2-phenylquinolin-4-yl)methoxy)benzyl)cyclopropanecarboxamide ID: ALA506057
PubChem CID: 44580802
Max Phase: Preclinical
Molecular Formula: C33H33N3O5
Molecular Weight: 551.64
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: O=C(NO)[C@H]1C[C@]1(Cc1ccc(OCc2cc(-c3ccccc3)nc3ccccc23)cc1)C(=O)N1CCC[C@H]1CO
Standard InChI: InChI=1S/C33H33N3O5/c37-20-25-9-6-16-36(25)32(39)33(19-28(33)31(38)35-40)18-22-12-14-26(15-13-22)41-21-24-17-30(23-7-2-1-3-8-23)34-29-11-5-4-10-27(24)29/h1-5,7-8,10-15,17,25,28,37,40H,6,9,16,18-21H2,(H,35,38)/t25-,28+,33-/m0/s1
Standard InChI Key: PHCNKOHEKZYJCZ-OYRZRQNVSA-N
Molfile:
RDKit 2D
41 46 0 0 0 0 0 0 0 0999 V2000
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-1.4110 -8.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-0.5473 -7.7019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.2870 -6.4780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.4091 -9.1540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1266 -9.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1260 -10.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4099 -10.8020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6927 -10.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6967 -9.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.6038 -7.9458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1865 -7.3606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.8193 -8.7430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-4.9846 -7.5726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.4079 -11.6279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-2.1221 -12.0425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1201 -12.8684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.1171 -14.5190 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4005 -14.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4057 -13.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-2.8321 -13.2849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5419 -12.8742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.2541 -13.2843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.2518 -14.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5414 -14.5165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4401 -8.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3700 -8.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7659 -7.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2004 -7.3503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3545 -6.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1342 -6.2667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.6855 -14.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6819 -15.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0348 -15.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7486 -15.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7411 -14.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.0236 -14.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
19 20 1 0
20 25 2 0
9 10 1 0
24 21 2 0
2 5 1 0
21 22 1 0
10 11 2 0
22 23 2 0
23 20 1 0
11 12 1 0
24 25 1 0
2 1 1 0
25 26 1 0
12 13 2 0
26 27 2 0
13 8 1 0
27 28 1 0
5 6 1 0
28 29 2 0
29 24 1 0
6 30 1 0
1 14 1 1
5 7 2 0
14 15 1 0
3 2 1 0
30 31 1 0
31 32 1 0
32 33 1 0
33 6 1 0
14 16 2 0
33 34 1 6
4 8 1 0
34 35 1 0
15 17 1 0
2 4 1 1
36 37 2 0
11 18 1 0
37 38 1 0
8 9 2 0
38 39 2 0
18 19 1 0
39 40 1 0
1 3 1 0
40 41 2 0
41 36 1 0
22 36 1 0
M END Associated Targets(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: 551.64Molecular Weight (Monoisotopic): 551.2420AlogP: 4.52#Rotatable Bonds: 9Polar Surface Area: 111.99Molecular Species: NEUTRALHBA: 6HBD: 3#RO5 Violations: 1HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski): 1CX Acidic pKa: 8.86CX Basic pKa: 3.66CX LogP: 4.28CX LogD: 4.26Aromatic Rings: 4Heavy Atoms: 41QED Weighted: 0.21Np Likeness Score: -0.45
References 1. Mazzola RD, Zhu Z, Sinning L, McKittrick B, Lavey B, Spitler J, Kozlowski J, Neng-Yang S, Zhou G, Guo Z, Orth P, Madison V, Sun J, Lundell D, Niu X.. (2008) Discovery of novel hydroxamates as highly potent tumor necrosis factor-alpha converting enzyme inhibitors. Part II: optimization of the S3' pocket., 18 (21): [PMID:18835710 ] [10.1016/j.bmcl.2008.09.045 ]