(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-(methyl-thiophen-2-yl-thiocarbamoylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

ID: ALA42083

PubChem CID: 44288906

Max Phase: Preclinical

Molecular Formula: C16H18N2O4S3

Molecular Weight: 398.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(SC(=S)N(C)c3cccs3)[C@H](C)[C@H]12

Standard InChI:  InChI=1S/C16H18N2O4S3/c1-7-11-10(8(2)19)14(20)18(11)12(15(21)22)13(7)25-16(23)17(3)9-5-4-6-24-9/h4-8,10-11,19H,1-3H3,(H,21,22)/t7-,8-,10-,11-/m1/s1

Standard InChI Key:  IPUPGPXMIBFBLJ-YJFSRANCSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    1.5125   -8.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3542   -8.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -8.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -8.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -7.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -7.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -7.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -7.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -8.1417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -7.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -9.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -5.7917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -6.6125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -6.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -9.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417  -10.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -6.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -8.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -6.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583   -7.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -6.8292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -6.8292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  1  0
  5  1  1  0
  6  5  1  0
  7  5  1  0
  8  9  1  0
  9  3  1  0
 10  8  1  0
 11 10  1  0
 12  2  1  0
 13 11  1  0
 14  8  2  0
 15  4  2  0
 16 11  2  0
 17  6  1  0
 18 13  1  0
 19 12  2  0
 20 16  1  0
 21 12  1  0
  7 22  1  1
 23 10  1  0
 17 24  1  1
 25 17  1  0
  6 26  1  1
  5 27  1  6
  3  7  1  0
  6  4  1  0
 20 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA42083

   (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[methyl(thiophen-2-yl)carbamothioyl]sulfanyl-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: 398.53

Molecular Weight (Monoisotopic): 398.0429

AlogP: 2.36

#Rotatable Bonds: 4

Polar Surface Area: 81.08

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.51

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: -1.96

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -0.11

References

1. Ohtake N, Imamura H, Kiyonaga H, Jona H, Ogawa M, Okada S, Shimizu A, Moriya M, Sato H, Tominaga Y, Yamada K, Nakano M, Ushijima R, Nakagawa S.  (1997)  Novel dithiocarbamate carbapenems1 with anti-MRSA activity,  7  (13): [10.1016/S0960-894X(97)00272-2]

Source

Source(1):

• Scientific Literature