(2R)-N-((1-(2-(2-((R)-2,5-Dihydro-2-methyl-2-((E)-2-methylbuta-1,3-dienyl)-5-oxothiophen-3-yloxy)acetamido)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-2,4-dihydroxy-3,3-dimethylbutanamide

ID: ALA4471699

PubChem CID: 71469116

Max Phase: Preclinical

Molecular Formula: C23H33N5O6S

Molecular Weight: 507.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/[C@@]1(C)SC(=O)C=C1OCC(=O)NCCn1cc(CNC(=O)[C@H](O)C(C)(C)CO)nn1

Standard InChI:  InChI=1S/C23H33N5O6S/c1-6-15(2)10-23(5)17(9-19(31)35-23)34-13-18(30)24-7-8-28-12-16(26-27-28)11-25-21(33)20(32)22(3,4)14-29/h6,9-10,12,20,29,32H,1,7-8,11,13-14H2,2-5H3,(H,24,30)(H,25,33)/b15-10+/t20-,23+/m0/s1

Standard InChI Key:  ZTNXSGFKCVTJGQ-IJFHWRKKSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4471699

   (2R)-2,4-dihydroxy-3,3-dimethyl-N-[[1-[2-[[2-[(2R)-2-methyl-2-[(1E)-2-methylbuta-1,3-dienyl]-5-oxothiophen-3-yl]oxyacetyl]amino]ethyl]triazol-4-yl]methyl]butanamide

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: 507.61

Molecular Weight (Monoisotopic): 507.2152

AlogP: 0.45

#Rotatable Bonds: 13

Polar Surface Area: 155.67

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.32

CX Basic pKa: 0.05

CX LogP: -0.23

CX LogD: -0.23

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: -0.25

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