tert-Butyl-2-(2-((R)-2,5-dihydro-2-methyl-2-((E)-2-methylbuta-1,3-dienyl)-5-oxothiophen-3-yloxy)acetamido)ethylcarbamate

ID: ALA4439825

PubChem CID: 71469114

Max Phase: Preclinical

Molecular Formula: C19H28N2O5S

Molecular Weight: 396.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/[C@@]1(C)SC(=O)C=C1OCC(=O)NCCNC(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C19H28N2O5S/c1-7-13(2)11-19(6)14(10-16(23)27-19)25-12-15(22)20-8-9-21-17(24)26-18(3,4)5/h7,10-11H,1,8-9,12H2,2-6H3,(H,20,22)(H,21,24)/b13-11+/t19-/m1/s1

Standard InChI Key:  HZRZDJSSJBFVQK-XSSIKURBSA-N

Molfile:  

 
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    8.2281  -14.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5506  -13.9119    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8894  -14.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5339  -13.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6813  -15.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8605  -15.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2702  -16.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959  -17.6684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750  -17.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5007  -18.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285  -16.8468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798  -18.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2055  -18.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333  -17.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -18.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4439825

   tert-butyl N-[2-[[2-[(2R)-2-methyl-2-[(1E)-2-methylbuta-1,3-dienyl]-5-oxothiophen-3-yl]oxyacetyl]amino]ethyl]carbamate

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: 396.51

Molecular Weight (Monoisotopic): 396.1719

AlogP: 2.69

#Rotatable Bonds: 8

Polar Surface Area: 93.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 0.13

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