ID: ALA446371

Max Phase: Preclinical

Molecular Formula: C16H20N2O9S

Molecular Weight: 416.41

Molecule Type: Small molecule

Representations

Synonyms (1): L-658758
Synonyms from Alternative Forms(1):

Canonical SMILES:  CO[C@H]1C(=O)N2C(C(=O)N3CCC[C@H]3C(=O)O)=C(COC(C)=O)CS(=O)(=O)[C@H]12

Standard InChI:  InChI=1S/C16H20N2O9S/c1-8(19)27-6-9-7-28(24,25)15-12(26-2)14(21)18(15)11(9)13(20)17-5-3-4-10(17)16(22)23/h10,12,15H,3-7H2,1-2H3,(H,22,23)/t10-,12-,15+/m0/s1

Standard InChI Key:  SMZXYXKZTNLAKY-ITDIGPHOSA-N

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

Properties

Molecular Weight: 416.41

Molecular Weight (Monoisotopic): 416.0890

AlogP: -1.51

#Rotatable Bonds: 5

Polar Surface Area: 147.59

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.02

CX Basic pKa:

CX LogP: -2.72

CX LogD: -6.19

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: 0.12

References

1. Thompson KR, Finke PE, Shah SK, Ashe BM, Dahlgren ME, Dellea PS, Fletcher DS, Hand KM, Maycock AL, Doherty JB.  (1993)  Inhibition of human leukocyte elastase. 7. Inhibition by 6-substituted penicillin amides.,  3  (11): [10.1016/S0960-894X(01)80941-0]

2. Subramanyam C, Bell MR, Ferguson E, Gordon RG, Dunlap RP, Franke C, Mura AJ.  (1995)  Inhibitors of human leukocyte elastase. 2.1 synthesis and sar of benzisothiazolinylmethyl aryl ethers,  5  (4): [10.1016/0960-894X(95)00028-R]

3. Leung D, Abbenante G, Fairlie DP..  (2000)  Protease inhibitors: current status and future prospects.,  43  (3): [PMID:10669559] [10.1021/jm990412m]

4. Finke PE, Shah SK, Ashe BM, Ball RG, Blacklock TJ, Bonney RJ, Brause KA, Chandler GO, Cotton M, Davies P..  (1992)  Inhibition of human leukocyte elastase. 4. Selection of a substituted cephalosporin (L-658,758) as a topical aerosol.,  35  (21): [PMID:1433188] [10.1021/jm00099a002]

5. Hagmann WK, Shah SK, Dorn CP, O'Grady LA, Hale JJ, Finke P, Thompson KR, Brause Ka, Ash BM, Weston H, Dahlgren M, Maycock AL, Dellea PS, Hand KM, Osinga DG, Bonney RJ, Davies P, Fletcher DS, Doherty JB.  (1991)  Prevention of human leukocyte elastase-mediated lung damage by 3-alkyl-4-azetidinones,  1  (10): [10.1016/S0960-894X(01)80463-7]

Source

Source(1):

• Scientific Literature