4-(Isoquinolin-5-ylsulfonyl)-1,4-diazepan-1-ium-2,2-dichloroacetate; Fasudil dichloroacetate

ID: ALA4459126

PubChem CID: 155091368

Max Phase: Preclinical

Molecular Formula: C16H19Cl2N3O4S

Molecular Weight: 291.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C(Cl)Cl.O=S(=O)(c1cccc2cnccc12)N1CCCNCC1

Standard InChI:  InChI=1S/C14H17N3O2S.C2H2Cl2O2/c18-20(19,17-9-2-6-15-8-10-17)14-4-1-3-12-11-16-7-5-13(12)14;3-1(4)2(5)6/h1,3-5,7,11,15H,2,6,8-10H2;1H,(H,5,6)

Standard InChI Key:  VNAPTWZEJOEXLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   24.6268   -5.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3413   -4.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9124   -4.6716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.6268   -5.9089    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.0556   -5.0840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3413   -3.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1354   -4.0205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9603   -4.0205    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.5478   -3.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8299   -5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8287   -6.0934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5435   -6.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5417   -4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2570   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2578   -6.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9730   -6.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6880   -6.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6832   -5.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9674   -4.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6752   -3.6072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6123   -2.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2141   -2.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3631   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0299   -2.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1509   -3.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4447   -3.0521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
  2  6  2  0
  8  7  2  0
  9  8  2  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19  8  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 22 24  1  0
 23 25  1  0
 24 26  1  0
 25 26  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 291.38

Molecular Weight (Monoisotopic): 291.1041

AlogP: 1.22

#Rotatable Bonds: 2

Polar Surface Area: 62.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.04

CX LogP: 0.32

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.90

Np Likeness Score: -1.64

References

1. Qi L, Lv T, Cheng Y, Yu M, Han H, Kong H, Xie W, Wang H, Zhang Y, Huang Z..  (2019)  Fasudil dichloroacetate (FDCA), an orally available agent with potent therapeutic efficiency on monocrotaline-induced pulmonary arterial hypertension rats.,  29  (14): [PMID:31088713] [10.1016/j.bmcl.2019.05.006]

Source

Source(1):

• Scientific Literature