2-((R)-2,5-Dihydro-2-methyl-2-((E)-2-methylbuta-1,3-dienyl)-5-oxothiophen-3-yloxy)-N-(2-azidoethyl)acetamide

ID: ALA4531860

PubChem CID: 118144560

Max Phase: Preclinical

Molecular Formula: C14H18N4O3S

Molecular Weight: 322.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/[C@@]1(C)SC(=O)C=C1OCC(=O)NCCN=[N+]=[N-]

Standard InChI:  InChI=1S/C14H18N4O3S/c1-4-10(2)8-14(3)11(7-13(20)22-14)21-9-12(19)16-5-6-17-18-15/h4,7-8H,1,5-6,9H2,2-3H3,(H,16,19)/b10-8+/t14-/m1/s1

Standard InChI Key:  GUFIEOGGCSKHND-QSYFUGGGSA-N

Molfile:  

 
     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    6.2003  -10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0251  -10.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2694   -9.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5939   -9.2470    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9349   -9.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0475   -9.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7439   -8.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862  -10.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107   -9.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7620   -9.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5834   -8.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0905   -9.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7274  -11.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089  -11.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4361  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178  -11.7216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7816  -12.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1449  -12.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266  -12.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8536  -12.9920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028  -13.7371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5483  -14.4826    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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  2  0
M  CHG  2  21   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4531860

   N-(2-azidoethyl)-2-[(2R)-2-methyl-2-[(1E)-2-methylbuta-1,3-dienyl]-5-oxothiophen-3-yl]oxyacetamide

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: 322.39

Molecular Weight (Monoisotopic): 322.1100

AlogP: 2.48

#Rotatable Bonds: 8

Polar Surface Area: 104.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.29

CX LogD: 1.17

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.24

Np Likeness Score: 0.67

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