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(R)-2-(3-tert-butyloxycarbonylamidophenyl)-4,5-dihydrothiazole-4-carboxylic acid
ID: ALA2087635
PubChem CID: 70689034
Max Phase: Preclinical
Molecular Formula: C15H18N2O4S
Molecular Weight: 322.39
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
Names and Identifiers
Canonical SMILES: CC(C)(C)OC(=O)Nc1cccc(C2=N[C@H](C(=O)O)CS2)c1
Standard InChI: InChI=1S/C15H18N2O4S/c1-15(2,3)21-14(20)16-10-6-4-5-9(7-10)12-17-11(8-22-12)13(18)19/h4-7,11H,8H2,1-3H3,(H,16,20)(H,18,19)/t11-/m0/s1
Standard InChI Key: YROWLKPEUPIUAV-NSHDSACASA-N
Molfile:
RDKit 2D
22 23 0 0 0 0 0 0 0 0999 V2000
-4.5056 -15.5541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.5068 -16.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7919 -16.7944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0755 -16.3810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0784 -15.5505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.7937 -15.1414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3644 -16.7904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2769 -17.6108 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4696 -17.7810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0582 -17.0659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6113 -16.4538 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
-1.1329 -18.5342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6168 -19.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.3123 -18.6191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.7962 -14.3164 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.0830 -13.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0854 -13.0767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-2.3673 -14.3121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.6540 -13.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9383 -14.3078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6565 -13.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9417 -13.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11 7 1 0
4 7 1 0
5 6 2 0
9 12 1 1
6 1 1 0
12 13 1 0
7 8 2 0
12 14 2 0
1 2 2 0
6 15 1 0
3 4 2 0
15 16 1 0
16 17 2 0
4 5 1 0
16 18 1 0
2 3 1 0
18 19 1 0
8 9 1 0
19 20 1 0
9 10 1 0
19 21 1 0
10 11 1 0
19 22 1 0
M END
Associated Targets(non-human)
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: 322.39 | Molecular Weight (Monoisotopic): 322.0987 | AlogP: 2.98 | #Rotatable Bonds: 3 |
Polar Surface Area: 87.99 | Molecular Species: ACID | HBA: 5 | HBD: 2 |
#RO5 Violations: ┄ | HBA (Lipinski): 6 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 3.26 | CX Basic pKa: 1.46 | CX LogP: 2.78 | CX LogD: -0.50 |
Aromatic Rings: 1 | Heavy Atoms: 22 | QED Weighted: 0.89 | Np Likeness Score: -0.52 |
References
1. Chen P, Horton LB, Mikulski RL, Deng L, Sundriyal S, Palzkill T, Song Y.. (2012) 2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases., 22 (19): [PMID:22921080] [10.1016/j.bmcl.2012.08.012] |