N-((S)-4-methyl-1-((4S,7R)-7-methyl-3-oxo-1-(pyridin-2-ylsulfonyl)azepan-4-ylamino)-1-oxopentan-2-yl)benzofuran-2-carboxamide

ID: ALA203665

Cas Number: 362505-84-8

PubChem CID: 6918602

Product Number: R613122, Order Now?

Max Phase: Phase

Molecular Formula: C27H32N4O6S

Molecular Weight: 540.64

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Relacatib | SB-462795 | Relacatib|362505-84-8|SB-462795|N-[(2S)-4-methyl-1-[[(4S,7R)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide|BL51M8CB8R|CHEMBL203665|Relacatib (USAN/INN)|N-((1S)-3-Methyl-1-((((4S,7R)-7-methyl-3-oxo-1-(2-pyridinylsulfonyl)hexahydro-1H-azepin-4-yl)amino)carbonyl)-butyl)-1-benzofuran-2-carboxamide|N-((S)-4-methyl-1-(((4S,7R)-7-methyl-3-oxo-1-(pyridin-2-ylsulfonyl)azepan-4-yl)amino)-1-oxopentan-2-yl)benzofuran-2-carboxamidShow More⌵

Canonical SMILES:  CC(C)C[C@H](NC(=O)c1cc2ccccc2o1)C(=O)N[C@H]1CC[C@@H](C)N(S(=O)(=O)c2ccccn2)CC1=O

Standard InChI:  InChI=1S/C27H32N4O6S/c1-17(2)14-21(30-27(34)24-15-19-8-4-5-9-23(19)37-24)26(33)29-20-12-11-18(3)31(16-22(20)32)38(35,36)25-10-6-7-13-28-25/h4-10,13,15,17-18,20-21H,11-12,14,16H2,1-3H3,(H,29,33)(H,30,34)/t18-,20+,21+/m1/s1

Standard InChI Key:  BWYBBMQLUKXECQ-GIVPXCGWSA-N

Molfile:  

     RDKit          2D

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    8.1405  -12.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9701  -12.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9260  -10.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3632  -11.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1621  -11.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1567   -9.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9306  -11.6714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9834   -9.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1351  -10.9439    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.5366  -11.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1297  -10.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8447  -10.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1127  -12.3702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5135  -13.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3393  -13.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7628  -12.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3595  -11.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  2  0
 17 19  1  0
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 21 14  1  6
  8 10  1  0
  5  6  2  0
 10 11  1  0
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  2  3  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 26 27  1  0
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 12 13  1  0
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  1  2  2  0
 22 29  1  0
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  3  4  2  0
 29 31  2  0
 10 15  2  0
 29 32  2  0
  4  6  1  0
 30 33  2  0
 12 16  1  1
 33 34  1  0
  6  7  1  0
 34 35  2  0
 16 17  1  0
 35 36  1  0
  7  8  1  0
 36 37  2  0
 37 30  1  0
 17 18  1  0
 25 38  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA203665

   relacatib

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 540.64

Molecular Weight (Monoisotopic): 540.2043

AlogP: 2.90

#Rotatable Bonds: 8

Polar Surface Area: 138.68

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.07

CX Basic pKa: ┄

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.45

Np Likeness Score: -0.78

References

1. Yamashita DS, Marquis RW, Xie R, Nidamarthy SD, Oh HJ, Jeong JU, Erhard KF, Ward KW, Roethke TJ, Smith BR, Cheng HY, Geng X, Lin F, Offen PH, Wang B, Nevins N, Head MS, Haltiwanger RC, Narducci Sarjeant AA, Liable-Sands LM, Zhao B, Smith WW, Janson CA, Gao E, Tomaszek T, McQueney M, James IE, Gress CJ, Zembryki DL, Lark MW, Veber DF..  (2006)  Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors.,  49  (5): [PMID:16509577] [10.1021/jm050915u]

2. Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong LT, Falgueyret JP, Kimmel DB, Lamontagne S, Léger S, LeRiche T, Li CS, Massé F, McKay DJ, Nicoll-Griffith DA, Oballa RM, Palmer JT, Percival MD, Riendeau D, Robichaud J, Rodan GA, Rodan SB, Seto C, Thérien M, Truong VL, Venuti MC, Wesolowski G, Young RN, Zamboni R, Black WC..  (2008)  The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K.,  18  (3): [PMID:18226527] [10.1016/j.bmcl.2007.12.047]

3. Allen JG, Fotsch C, Babij P..  (2010)  Emerging targets in osteoporosis disease modification.,  53  (11): [PMID:20218623] [10.1021/jm9018756]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names