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

ID: ALA4556828

PubChem CID: 136446118

Max Phase: Preclinical

Molecular Formula: C14H19N3O2S

Molecular Weight: 293.39

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H19N3O2S/c1-4-10(2)9-14(3)12(18)11(13(19)20-14)7-5-6-8-16-17-15/h4,9,18H,1,5-8H2,2-3H3/b10-9+/t14-/m1/s1

Standard InChI Key:  YWCFDTCBMVZYIG-ATWMFIQVSA-N

Molfile:  

 
     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   24.6173  -18.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4426  -18.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6869  -18.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0112  -17.6273    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.3518  -18.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4652  -17.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2785  -17.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6029  -18.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9271  -17.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1782  -18.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0001  -17.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5066  -17.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1443  -19.5778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9360  -19.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6133  -20.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1066  -20.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7838  -21.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2772  -22.3756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9567  -23.1278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6339  -23.8837    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
 10 12  2  0
  1 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  2  0
M  CHG  2  19   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4556828

   ---

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: 293.39

Molecular Weight (Monoisotopic): 293.1198

AlogP: 4.44

#Rotatable Bonds: 7

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: 6.59

CX Basic pKa: ┄

CX LogP: 3.26

CX LogD: 2.28

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.25

Np Likeness Score: 1.68

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