(E)-N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-4-phenylbut-1-ene-1-sulfonamide

ID: ALA428030

PubChem CID: 44435057

Max Phase: Preclinical

Molecular Formula: C22H33NO6S2

Molecular Weight: 471.64

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H33NO6S2/c24-15-18-20(25)21(26)19(22(29-18)30-17-12-5-2-6-13-17)23-31(27,28)14-8-7-11-16-9-3-1-4-10-16/h1,3-4,8-10,14,17-26H,2,5-7,11-13,15H2/b14-8+/t18-,19-,20-,21-,22-/m0/s1

Standard InChI Key:  RVHXJNMKPZMFIE-QPHOAESRSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA428030

   (E)-N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-3-yl)-4-phenylbut-1-ene-1-sulfonamide

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: 471.64

Molecular Weight (Monoisotopic): 471.1749

AlogP: 1.93

#Rotatable Bonds: 9

Polar Surface Area: 116.09

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.85

CX Basic pKa: ┄

CX LogP: 2.36

CX LogD: 2.25

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: 0.58

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