(2R,3R,4S)-4-(dichloromethylsulfonamido)-3-isobutyramido-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid

ID: ALA473893

Chembl Id: CHEMBL473893

PubChem CID: 24768934

Max Phase: Preclinical

Molecular Formula: C14H22Cl2N2O9S

Molecular Weight: 465.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BCX-2855 | CHEMBL473893|SCHEMBL6017830|BCX-2855|(2R,3R,4S)-4-(dichloromethylsulfonylamino)-3-(2-methylpropanoylamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

Canonical SMILES:  CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1NS(=O)(=O)C(Cl)Cl

Standard InChI:  InChI=1S/C14H22Cl2N2O9S/c1-5(2)12(22)17-9-6(18-28(25,26)14(15)16)3-8(13(23)24)27-11(9)10(21)7(20)4-19/h3,5-7,9-11,14,18-21H,4H2,1-2H3,(H,17,22)(H,23,24)/t6-,7+,9+,10+,11+/m0/s1

Standard InChI Key:  VCJGUPDYWNYSJW-CNYIRLTGSA-N

Alternative Forms

1. Parent:

   

   ALA473893

   (2R,3R,4S)-4-(dichloromethylsulfonylamino)-3-(2-methylpropanoylamino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid

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: 465.31

Molecular Weight (Monoisotopic): 464.0423

AlogP: -1.74

#Rotatable Bonds: 9

Polar Surface Area: 182.49

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.39

CX Basic pKa: ┄

CX LogP: -0.77

CX LogD: -4.21

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.22

Np Likeness Score: 0.63

References

1. Prado-Prado FJ, Martinez de la Vega O, Uriarte E, Ubeira FM, Chou KC, González-Díaz H..  (2009)  Unified QSAR approach to antimicrobials. 4. Multi-target QSAR modeling and comparative multi-distance study of the giant components of antiviral drug-drug complex networks.,  17  (2): [PMID:19112024] [10.1016/j.bmc.2008.11.075]

Source

Source(1):

• Scientific Literature