(6S,7S)-7-{2-(2-Amino-thiazol-4-yl)-2-[(E)-methoxyimino]-acetylamino}-3-[(1E,3E)-5-(1-methyl-1H-tetrazol-5-ylsulfanyl)-penta-1,3-dienyl]-8-oxo-4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA304163

PubChem CID: 44311155

Max Phase: Preclinical

Molecular Formula: C20H21N9O5S3

Molecular Weight: 563.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/N=C(/C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(/C=C/C=C/CSc3nnnn3C)SC[C@H]12)c1csc(N)n1

Standard InChI:  InChI=1S/C20H21N9O5S3/c1-28-20(24-26-27-28)35-7-5-3-4-6-12-15(18(32)33)29-11(9-36-12)14(17(29)31)23-16(30)13(25-34-2)10-8-37-19(21)22-10/h3-6,8,11,14H,7,9H2,1-2H3,(H2,21,22)(H,23,30)(H,32,33)/b5-3+,6-4+,25-13+/t11-,14+/m1/s1

Standard InChI Key:  MJXPNYPFQITTNS-MVRDWKHWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA304163

   (6S,7S)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1E,3E)-5-(1-methyltetrazol-5-yl)sulfanylpenta-1,3-dienyl]-8-oxo-4-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: 563.65

Molecular Weight (Monoisotopic): 563.0828

AlogP: 0.24

#Rotatable Bonds: 10

Polar Surface Area: 190.81

Molecular Species: ACID

HBA: 14

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.96

CX Basic pKa: 3.71

CX LogP: -0.16

CX LogD: -2.95

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.12

Np Likeness Score: -0.85

References

1. Aszodi J, Bonnet A, Chantot J, Costerousse G, Didierlaurent S, Teutsch G.  (1993)  Vinylogous vs arylogous isocephems,  3  (11): [10.1016/S0960-894X(01)80930-6]

Source

Source(1):

• Scientific Literature