6-Chloro-naphthalene-2-sulfonic acid{(S)-2-oxo-1-[2-oxo-2-((1R,5S)-8-oxo-1,5,6,8-tetrahydro-2H,4H-1,5-methano-pyrido[1,2-a][1,5]diazocin-3-yl)-ethyl]-piperidin-3-yl}-amide

ID: ALA1923468

PubChem CID: 53488415

Max Phase: Preclinical

Molecular Formula: C28H29ClN4O5S

Molecular Weight: 569.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CN1CCC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O)N1C[C@@H]2C[C@H](C1)c1cccc(=O)n1C2

Standard InChI:  InChI=1S/C28H29ClN4O5S/c29-22-8-6-20-13-23(9-7-19(20)12-22)39(37,38)30-24-3-2-10-31(28(24)36)17-27(35)32-14-18-11-21(16-32)25-4-1-5-26(34)33(25)15-18/h1,4-9,12-13,18,21,24,30H,2-3,10-11,14-17H2/t18-,21+,24-/m0/s1

Standard InChI Key:  FLGSVBQCPOVGER-VNZMSGEBSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1923468

   6-Chloro-N-((3s)-2-Oxo-1-(2-Oxo-2-((5s)-8-Oxo-5,6-Dihydro-1h-1,5-Methanopyrido[1,2-A][1,5]diazocin-3(2h,4h,8h)-Yl)ethyl)piperidin-3-Yl)naphthalene-2-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: 569.08

Molecular Weight (Monoisotopic): 568.1547

AlogP: 2.57

#Rotatable Bonds: 5

Polar Surface Area: 108.79

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.04

CX Basic pKa: ┄

CX LogP: 1.16

CX LogD: 1.16

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.51

Np Likeness Score: -1.31

References

1. Shi Y, O'Connor SP, Sitkoff D, Zhang J, Shi M, Bisaha SN, Wang Y, Li C, Ruan Z, Lawrence RM, Klei HE, Kish K, Liu EC, Seiler SM, Schweizer L, Steinbacher TE, Schumacher WA, Robl JA, Macor JE, Atwal KS, Stein PD..  (2011)  Arylsulfonamidopiperidone derivatives as a novel class of factor Xa inhibitors.,  21  (24): [PMID:22041058] [10.1016/j.bmcl.2011.06.098]

Source

Source(1):

• Scientific Literature