(7R,7aR)-7-[D-(-)-2-amino-2-phenylacetamido]-3-[5-methyl-(1,3,4-thiadiazol-2-yl)thiomethyl]-3-cephem-4-carboxylic acid

ID: ALA3276278

Chembl Id: CHEMBL3276278

PubChem CID: 90679447

Max Phase: Preclinical

Molecular Formula: C19H19N5O4S3

Molecular Weight: 477.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nnc(SCC2=C(C(=O)O)N3C(=O)[C@@H](NC(=O)[C@H](N)c4ccccc4)[C@H]3SC2)s1

Standard InChI:  InChI=1S/C19H19N5O4S3/c1-9-22-23-19(31-9)30-8-11-7-29-17-13(16(26)24(17)14(11)18(27)28)21-15(25)12(20)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,20H2,1H3,(H,21,25)(H,27,28)/t12-,13-,17-/m1/s1

Standard InChI Key:  PSAVXSZVPAYPEQ-PBFPGSCMSA-N

Alternative Forms

1. Parent:

   

   ALA3276278

   (6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]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: 477.59

Molecular Weight (Monoisotopic): 477.0599

AlogP: 1.38

#Rotatable Bonds: 7

Polar Surface Area: 138.51

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 2.72

CX Basic pKa: 7.23

CX LogP: -1.83

CX LogD: -2.18

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -0.67

References

1. Wheeler WJ, Wright WE, Line VD, Froggé JA..  (1977)  Orally active esters of cephalosporin antibiotics. Synthesis and biological properties of acyloxymethyl esters of 7-(D-2-amino-2-phenylacetamido)-3-[5-methyl-(1,3,4-thiadiazol-2-yl)thiomethyl]-3-cephem-4-carboxylic acid.,  20  (9): [PMID:21963] [10.1021/jm00219a009]

Source

Source(1):

• Scientific Literature