(S)-4'-azidoblebbistatin

ID: ALA4166562

PubChem CID: 101583485

Max Phase: Preclinical

Molecular Formula: C18H15N5O2

Molecular Weight: 333.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H15N5O2/c1-11-2-7-15-14(10-11)16(24)18(25)8-9-23(17(18)20-15)13-5-3-12(4-6-13)21-22-19/h2-7,10,25H,8-9H2,1H3/t18-/m1/s1

Standard InChI Key:  BJOZZMIAIXTDEI-GOSISDBHSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   37.3335  -10.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3323  -11.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0404  -11.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0386   -9.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6257   -9.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7472  -10.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7460  -11.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4561  -11.4519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4585   -9.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4585   -8.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.1732  -10.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1699  -11.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9519  -11.2983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4385  -10.6341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9572   -9.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2013  -12.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6501  -12.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8989  -13.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6983  -13.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2485  -13.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9967  -12.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1662   -9.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.9488  -14.4101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4004  -15.0159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.8183  -15.5927    0.0000 N   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
 23 24  2  0
 24 25  2  0
M  CHG  2  24   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4166562

   (3aS)-1-(4-azidophenyl)-3a-hydroxy-6-methyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-one

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: 333.35

Molecular Weight (Monoisotopic): 333.1226

AlogP: 3.80

#Rotatable Bonds: 2

Polar Surface Area: 101.66

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.54

CX Basic pKa: 2.59

CX LogP: 3.30

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: 0.05

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