tert-butyl 1-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-ylamino)-1-oxo-4-phenylbutan-2-ylcarbamate

ID: ALA238991

PubChem CID: 44435061

Max Phase: Preclinical

Molecular Formula: C27H42N2O7S

Molecular Weight: 538.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)ON[C@@H](CCc1ccccc1)C(=O)N[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1SC1CCCCC1

Standard InChI:  InChI=1S/C27H42N2O7S/c1-27(2,3)26(34)36-29-19(15-14-17-10-6-4-7-11-17)24(33)28-21-23(32)22(31)20(16-30)35-25(21)37-18-12-8-5-9-13-18/h4,6-7,10-11,18-23,25,29-32H,5,8-9,12-16H2,1-3H3,(H,28,33)/t19-,20-,21-,22-,23-,25-/m0/s1

Standard InChI Key:  IYLQTEHCQAINBA-RYBBFAMKSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA238991

   tert-butyl 1-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-ylamino)-1-oxo-4-phenylbutan-2-ylcarbamate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.71

Molecular Weight (Monoisotopic): 538.2713

AlogP: 2.07

#Rotatable Bonds: 10

Polar Surface Area: 137.35

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.50

CX Basic pKa: 3.31

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.28

Np Likeness Score: 0.49

References

1. Metaferia BB, Fetterolf BJ, Shazad-Ul-Hussan S, Moravec M, Smith JA, Ray S, Gutierrez-Lugo MT, Bewley CA..  (2007)  Synthesis of natural product-inspired inhibitors of Mycobacterium tuberculosis mycothiol-associated enzymes: the first inhibitors of GlcNAc-Ins deacetylase.,  50  (25): [PMID:18020307] [10.1021/jm070669h]

Source

Source(1):

• Scientific Literature