ID: ALA2419504

Max Phase: Preclinical

Molecular Formula: C21H16N2O4S

Molecular Weight: 392.44

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(NCc1ccc(S(=O)(=O)c2ccccc2)cc1)c1cc2ccncc2o1

Standard InChI:  InChI=1S/C21H16N2O4S/c24-21(19-12-16-10-11-22-14-20(16)27-19)23-13-15-6-8-18(9-7-15)28(25,26)17-4-2-1-3-5-17/h1-12,14H,13H2,(H,23,24)

Standard InChI Key:  IPFCGFBLRONVPM-UHFFFAOYSA-N

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

Properties

Molecular Weight: 392.44

Molecular Weight (Monoisotopic): 392.0831

AlogP: 3.59

#Rotatable Bonds: 5

Polar Surface Area: 89.27

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.17

CX Basic pKa: 3.75

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -1.37

References

1. Dragovich PS, Bair KW, Baumeister T, Ho YC, Liederer BM, Liu X, Liu Y, O'Brien T, Oeh J, Sampath D, Skelton N, Wang L, Wang W, Wu H, Xiao Y, Yuen PW, Zak M, Zhang L, Zheng X..  (2013)  Identification of 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-derived ureas as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT).,  23  (17): [PMID:23899614] [10.1016/j.bmcl.2013.06.090]

2. Zheng X, Bauer P, Baumeister T, Buckmelter AJ, Caligiuri M, Clodfelter KH, Han B, Ho YC, Kley N, Lin J, Reynolds DJ, Sharma G, Smith CC, Wang Z, Dragovich PS, Gunzner-Toste J, Liederer BM, Ly J, O'Brien T, Oh A, Wang L, Wang W, Xiao Y, Zak M, Zhao G, Yuen PW, Bair KW..  (2013)  Structure-based discovery of novel amide-containing nicotinamide phosphoribosyltransferase (nampt) inhibitors.,  56  (16): [PMID:23859118] [10.1021/jm4008664]

3. Zak M, Liederer BM, Sampath D, Yuen PW, Bair KW, Baumeister T, Buckmelter AJ, Clodfelter KH, Cheng E, Crocker L, Fu B, Han B, Li G, Ho YC, Lin J, Liu X, Ly J, O'Brien T, Reynolds DJ, Skelton N, Smith CC, Tay S, Wang W, Wang Z, Xiao Y, Zhang L, Zhao G, Zheng X, Dragovich PS..  (2015)  Identification of nicotinamide phosphoribosyltransferase (NAMPT) inhibitors with no evidence of CYP3A4 time-dependent inhibition and improved aqueous solubility.,  25  (3): [PMID:25556090] [10.1016/j.bmcl.2014.12.026]

4. Zak M, Yuen PW, Liu X, Patel S, Sampath D, Oeh J, Liederer BM, Wang W, O'Brien T, Xiao Y, Skelton N, Hua R, Sodhi J, Wang Y, Zhang L, Zhao G, Zheng X, Ho YC, Bair KW, Dragovich PS..  (2016)  Minimizing CYP2C9 Inhibition of Exposed-Pyridine NAMPT (Nicotinamide Phosphoribosyltransferase) Inhibitors.,  59  (18): [PMID:27541271] [10.1021/acs.jmedchem.6b00697]

Source

Source(1):

• Scientific Literature