(R)-3-(6-Azidohexanoyl)-4-hydroxy-5-methyl-5-((E)-2-methylbuta-1,3-dienyl)thiophen-2(5H)-one

ID: ALA4457240

PubChem CID: 155525537

Max Phase: Preclinical

Molecular Formula: C16H21N3O3S

Molecular Weight: 335.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21N3O3S/c1-4-11(2)10-16(3)14(21)13(15(22)23-16)12(20)8-6-5-7-9-18-19-17/h4,10,21H,1,5-9H2,2-3H3/b11-10+/t16-/m1/s1

Standard InChI Key:  ISYQDIQOASFRNY-SIFUEBAJSA-N

Molfile:  

 
     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    6.2620  -15.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0891  -15.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3340  -14.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6568  -13.7456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960  -14.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1140  -13.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633  -13.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2455  -14.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5683  -14.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8176  -14.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6413  -13.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7881  -15.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5835  -15.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2601  -16.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7546  -17.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4312  -17.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429  -13.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4013  -15.5726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9255  -18.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6022  -19.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0966  -19.9207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9134  -19.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7312  -19.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  3  6  2  0
  5  7  1  6
  5  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
  1 12  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  2  0
 13 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  2  0
M  CHG  2  22   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4457240

   ---

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: 335.43

Molecular Weight (Monoisotopic): 335.1304

AlogP: 4.40

#Rotatable Bonds: 9

Polar Surface Area: 103.13

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.85

CX Basic pKa: ┄

CX LogP: 3.49

CX LogD: -0.15

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.17

Np Likeness Score: 1.44

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