(6R,7R)-7-(2-(1H-indol-1-yl)acetamido)-3-((5-methyl-1,3,4-thiadiazol-2-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA3248699

Chembl Id: CHEMBL3248699

PubChem CID: 90673408

Max Phase: Preclinical

Molecular Formula: C21H19N5O4S3

Molecular Weight: 501.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)Cn4ccc5ccccc54)[C@H]3SC2)s1

Standard InChI:  InChI=1S/C21H19N5O4S3/c1-11-23-24-21(33-11)32-10-13-9-31-19-16(18(28)26(19)17(13)20(29)30)22-15(27)8-25-7-6-12-4-2-3-5-14(12)25/h2-7,16,19H,8-10H2,1H3,(H,22,27)(H,29,30)/t16-,19-/m1/s1

Standard InChI Key:  DXADWKFUUBKQFC-VQIMIIECSA-N

Alternative Forms

1. Parent:

   

   ALA3248699

   (6R,7R)-7-[(2-indol-1-ylacetyl)amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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: 501.62

Molecular Weight (Monoisotopic): 501.0599

AlogP: 2.33

#Rotatable Bonds: 7

Polar Surface Area: 117.42

Molecular Species: ACID

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.06

CX Basic pKa: 0.24

CX LogP: 1.42

CX LogD: -2.04

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -1.34

References

1. Nudelman A, Karoly H, Braun F, Böhme EH, Erickson RC..  (1978)  Semisynthetic cephalosporins. Synthesis and structure-activity relationships of 7-(1-pyrryl)- and 7-(1-indolyl)acetamidocephalosporin derivatives.,  21  (9): [PMID:722761] [10.1021/jm00207a022]

Source

Source(1):

• Scientific Literature