ID: ALA434965

Max Phase: Preclinical

Molecular Formula: C9H15NO3S

Molecular Weight: 217.29

Molecule Type: Small molecule

Representations

Synonyms (1): D-Captopril
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H](CS)C(=O)N1CCC[C@@H]1C(=O)O

Standard InChI:  InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7-/m1/s1

Standard InChI Key:  FAKRSMQSSFJEIM-RNFRBKRXSA-N

Molecule Features

Natural Product: Yes

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: 217.29

Molecular Weight (Monoisotopic): 217.0773

AlogP: 0.63

#Rotatable Bonds: 3

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.02

CX Basic pKa:

CX LogP: 0.73

CX LogD: -2.42

Aromatic Rings: 0

Heavy Atoms: 14

QED Weighted: 0.68

Np Likeness Score: 0.11

References

1. Wermuth CG..  (2004)  Selective optimization of side activities: another way for drug discovery.,  47  (6): [PMID:14998318] [10.1021/jm030480f]

2. Gillner D, Armoush N, Holz RC, Becker DP..  (2009)  Inhibitors of bacterial N-succinyl-L,L-diaminopimelic acid desuccinylase (DapE) and demonstration of in vitro antimicrobial activity.,  19  (22): [PMID:19822427] [10.1016/j.bmcl.2009.09.077]

3. Gan M, Liu Y, Bai Y, Guan Y, Li L, Gao R, He W, You X, Li Y, Yu L, Xiao C..  (2013)  Polyketides with New Delhi metallo-β-lactamase 1 inhibitory activity from Penicillium sp.,  76  (9): [PMID:23972215] [10.1021/np4000944]

4. Li N, Xu Y, Xia Q, Bai C, Wang T, Wang L, He D, Xie N, Li L, Wang J, Zhou HG, Xu F, Yang C, Zhang Q, Yin Z, Guo Y, Chen Y..  (2014)  Simplified captopril analogues as NDM-1 inhibitors.,  24  (1): [PMID:24269122] [10.1016/j.bmcl.2013.10.068]

5.  (2006)  Compounds inhibiting the binding of sap for treating osteoarthritis, 

6. Chen AY, Thomas PW, Stewart AC, Bergstrom A, Cheng Z, Miller C, Bethel CR, Marshall SH, Credille CV, Riley CL, Page RC, Bonomo RA, Crowder MW, Tierney DL, Fast W, Cohen SM..  (2017)  Dipicolinic Acid Derivatives as Inhibitors of New Delhi Metallo-β-lactamase-1.,  60  (17): [PMID:28809565] [10.1021/acs.jmedchem.7b00407]

7. Liu S, Jing L, Yu ZJ, Wu C, Zheng Y, Zhang E, Chen Q, Yu Y, Guo L, Wu Y, Li GB..  (2018)  ((S)-3-Mercapto-2-methylpropanamido)acetic acid derivatives as metallo-β-lactamase inhibitors: Synthesis, kinetic and crystallographic studies.,  145  [PMID:29353720] [10.1016/j.ejmech.2018.01.032]

8. Jin WB,Xu C,Cheng Q,Qi XL,Gao W,Zheng Z,Chan EWC,Leung YC,Chan TH,Wong KY,Chen S,Chan KF.  (2018)  Investigation of synergistic antimicrobial effects of the drug combinations of meropenem and 1,2-benzisoselenazol-3(2H)-one derivatives on carbapenem-resistant Enterobacteriaceae producing NDM-1.,  155  [PMID:29894943] [10.1016/j.ejmech.2018.06.007]

9. Ma G,Wang S,Wu K,Zhang W,Ahmad A,Hao Q,Lei X,Zhang H.  (2021)  Structure-guided optimization of D-captopril for discovery of potent NDM-1 inhibitors.,  29  [PMID:33302045] [10.1016/j.bmc.2020.115902]

10. Wang T, Xu K, Zhao L, Tong R, Xiong L, Shi J..  (2021)  Recent research and development of NDM-1 inhibitors.,  223  [PMID:34225181] [10.1016/j.ejmech.2021.113667]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data