(6R,7R)-3-(acetoxymethyl)-7-(3-ethoxy-3-oxo-2-(1H-pyrrol-1-yl)propanamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA3248696

Chembl Id: CHEMBL3248696

PubChem CID: 90673405

Max Phase: Preclinical

Molecular Formula: C19H21N3O8S

Molecular Weight: 451.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(C)=O)CS[C@H]12)n1cccc1

Standard InChI:  InChI=1S/C19H21N3O8S/c1-3-29-19(28)14(21-6-4-5-7-21)15(24)20-12-16(25)22-13(18(26)27)11(8-30-10(2)23)9-31-17(12)22/h4-7,12,14,17H,3,8-9H2,1-2H3,(H,20,24)(H,26,27)/t12-,14?,17-/m1/s1

Standard InChI Key:  IXIXPUJBMQNTET-ZYFOBHMOSA-N

Alternative Forms

1. Parent:

   

   ALA3248696

   (6R,7R)-3-(acetyloxymethyl)-7-[(3-ethoxy-3-oxo-2-pyrrol-1-ylpropanoyl)amino]-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: 451.46

Molecular Weight (Monoisotopic): 451.1049

AlogP: -0.11

#Rotatable Bonds: 8

Polar Surface Area: 144.24

Molecular Species: ACID

HBA: 9

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.30

CX Basic pKa:

CX LogP: -0.26

CX LogD: -3.68

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: 0.21

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