(R)-3-(3-Azidopropyl)-4-hydroxy-5-methyl-5-((E)-2-methylbuta-1,3-dienyl)thiophen-2(5H)-one

ID: ALA4444456

PubChem CID: 136996815

Max Phase: Preclinical

Molecular Formula: C13H17N3O2S

Molecular Weight: 279.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/[C@@]1(C)SC(=O)C(CCCN=[N+]=[N-])=C1O

Standard InChI:  InChI=1S/C13H17N3O2S/c1-4-9(2)8-13(3)11(17)10(12(18)19-13)6-5-7-15-16-14/h4,8,17H,1,5-7H2,2-3H3/b9-8+/t13-/m1/s1

Standard InChI Key:  DEBFCQYYJPJZEV-MMQHEFTJSA-N

Molfile:  

 
     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   33.5177  -13.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0291  -11.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8540  -11.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0983  -10.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4228  -10.3746    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.7638  -10.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8762  -10.5842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5140   -9.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0152  -11.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3398  -10.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5911  -11.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4126   -9.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9199  -10.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5564  -12.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3471  -12.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0246  -13.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1952  -14.4634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6907  -15.1182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1838  -15.7753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  4  7  2  0
  6  8  1  6
  6  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 11 13  2  0
  2 14  1  0
  3 15  1  0
 15 16  1  0
 16  1  1  0
  1 17  1  0
 17 18  2  0
 18 19  2  0
M  CHG  2  18   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4444456

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 279.36

Molecular Weight (Monoisotopic): 279.1041

AlogP: 4.05

#Rotatable Bonds: 6

Polar Surface Area: 86.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.54

CX Basic pKa: ┄

CX LogP: 2.82

CX LogD: 1.79

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.26

Np Likeness Score: 1.75

References

1. Bommineni GR, Kapilashrami K, Cummings JE, Lu Y, Knudson SE, Gu C, Walker SG, Slayden RA, Tonge PJ..  (2016)  Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity.,  59  (11): [PMID:27187871] [10.1021/acs.jmedchem.6b00236]

Source

Source(1):

• Scientific Literature