(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-{[(3S,5S)-5-[(1E)-1-(methoxyimino)-2-[(methylsulfamoyl)amino]ethyl]pyrrolidin-3-yl]sulfanyl}-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ID: ALA388019

Chembl Id: CHEMBL388019

PubChem CID: 16126569

Max Phase: Preclinical

Molecular Formula: C18H29N5O7S2

Molecular Weight: 491.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNS(=O)(=O)NC/C(=N\OC)[C@@H]1C[C@H](SC2=C(C(=O)O)N3C(=O)[C@H]([C@@H](C)O)[C@H]3[C@H]2C)CN1

Standard InChI:  InChI=1S/C18H29N5O7S2/c1-8-14-13(9(2)24)17(25)23(14)15(18(26)27)16(8)31-10-5-11(20-6-10)12(22-30-4)7-21-32(28,29)19-3/h8-11,13-14,19-21,24H,5-7H2,1-4H3,(H,26,27)/b22-12+/t8-,9-,10+,11+,13-,14-/m1/s1

Standard InChI Key:  KXUDAUFRWDYOHI-IJZKTRLRSA-N

Alternative Forms

1. Parent:

   

   ALA388019

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-3-[(3S,5S)-5-[(E)-N-methoxy-C-[(methylsulfamoylamino)methyl]carbonimidoyl]pyrrolidin-3-yl]sulfanyl-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-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: 491.59

Molecular Weight (Monoisotopic): 491.1508

AlogP: -1.34

#Rotatable Bonds: 10

Polar Surface Area: 169.66

Molecular Species: ZWITTERION

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.65

CX Basic pKa: 8.94

CX LogP: -5.12

CX LogD: -5.13

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.14

Np Likeness Score: 0.34

References

1. Jeon H, Jo NH, Yoo KH, Choi JH, Cho H, Cho JH, Oh CH..  (2007)  Synthesis and antibacterial evaluation of 1beta-methyl-2-[5-(1-methoxyimino-2-substituted sulfonamide ethyl)pyrrolidin-3-ylthio]carbapenems and their related compounds.,  42  (3): [PMID:17156896] [10.1016/j.ejmech.2006.10.006]

Source

Source(1):

• Scientific Literature