ID: ALA482858

Max Phase: Unknown

Molecular Formula: C16H21N3O8S

Molecular Weight: 415.42

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-757790
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(=O)O)[C@H]2SC1

Standard InChI:  InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1

Standard InChI Key:  HOKIDJSKDBPKTQ-GLXFQSAKSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 415.42

Molecular Weight (Monoisotopic): 415.1049

AlogP: -1.13

#Rotatable Bonds: 9

Polar Surface Area: 176.33

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.83

CX Basic pKa: 9.22

CX LogP: -4.39

CX LogD: -7.64

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: 0.68

References

1. Girlich D, Leclercq R, Naas T, Nordmann P..  (2007)  Molecular and biochemical characterization of the chromosome-encoded class A beta-lactamase BCL-1 from Bacillus clausii.,  51  (11): [PMID:17846134] [10.1128/aac.00537-07]

2. PubChem BioAssay data set, 

3. Sarkar A, Anderson KC, Kellogg GE..  (2012)  Computational analysis of structure-based interactions and ligand properties can predict efflux effects on antibiotics.,  52  [PMID:22483632] [10.1016/j.ejmech.2012.03.008]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Fei Y,Wu J,An HW,Zhu K,Peng B,Cai J,Zhang Y,Li LL,Wang H,Huang Z.  (2020)  Identification of New Nitric Oxide-Donating Peptides with Dual Biofilm Eradication and Antibacterial Activities for Intervention of Device-Related Infections.,  63  (17): [PMID:32787095] [10.1021/acs.jmedchem.9b01832]

6. Dhanda G, Sarkar P, Samaddar S, Haldar J..  (2019)  Battle against Vancomycin-Resistant Bacteria: Recent Developments in Chemical Strategies.,  62  (7.0): [PMID:30404451] [10.1021/acs.jmedchem.8b01093]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names