(S)-4'-chloroblebbistatin

ID: ALA4165503

PubChem CID: 145955394

Max Phase: Preclinical

Molecular Formula: C18H15ClN2O2

Molecular Weight: 326.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)C(=O)[C@]1(O)CCN(c3ccc(Cl)cc3)C1=N2

Standard InChI:  InChI=1S/C18H15ClN2O2/c1-11-2-7-15-14(10-11)16(22)18(23)8-9-21(17(18)20-15)13-5-3-12(19)4-6-13/h2-7,10,23H,8-9H2,1H3/t18-/m1/s1

Standard InChI Key:  DHAADFMSKONJNO-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
   17.5888  -10.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5877  -11.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2957  -11.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2939  -10.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8810  -10.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0026  -10.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0014  -11.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7115  -11.6954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7138  -10.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7139   -9.2278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4285  -10.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4252  -11.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2073  -11.5418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6939  -10.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2125  -10.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4567  -12.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9054  -12.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1543  -13.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9537  -13.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5038  -13.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2520  -12.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4215   -9.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2041  -14.6536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  1  5  1  0
  6  7  1  0
  6  9  1  0
  7  8  1  0
  8 12  2  0
 11  9  1  0
  9 10  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 11 22  1  1
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4165503

   ---

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: 326.78

Molecular Weight (Monoisotopic): 326.0822

AlogP: 3.52

#Rotatable Bonds: 1

Polar Surface Area: 52.90

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.54

CX Basic pKa: 2.63

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.87

Np Likeness Score: -0.12

References

1. Roman BI, Verhasselt S, Stevens CV..  (2018)  Medicinal Chemistry and Use of Myosin II Inhibitor ( S)-Blebbistatin and Its Derivatives.,  61  (21): [PMID:29878759] [10.1021/acs.jmedchem.8b00503]

Source

Source(1):

• Scientific Literature