ID: ALA4206119

Max Phase: Phase

Molecular Formula: C32H47N5O6S

Molecular Weight: 629.82

Molecule Type: Small molecule

Representations

Synonyms (4): Mesupron | Upamostat | Wx-671 | WX-671
Synonyms from Alternative Forms(4):

Canonical SMILES:  CCOC(=O)N1CCN(C(=O)[C@H](Cc2cccc(/C(N)=N\O)c2)NS(=O)(=O)c2c(C(C)C)cc(C(C)C)cc2C(C)C)CC1

Standard InChI:  InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)28(17-23-10-9-11-24(16-23)30(33)34-40)35-44(41,42)29-26(21(4)5)18-25(20(2)3)19-27(29)22(6)7/h9-11,16,18-22,28,35,40H,8,12-15,17H2,1-7H3,(H2,33,34)/t28-/m0/s1

Standard InChI Key:  HUASEDVYRABWCV-NDEPHWFRSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 629.82

Molecular Weight (Monoisotopic): 629.3247

AlogP: 4.34

#Rotatable Bonds: 11

Polar Surface Area: 154.63

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.24

CX Basic pKa: 4.96

CX LogP: 4.85

CX LogD: 4.78

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: -0.89

References

1. Buckley BJ, Aboelela A, Minaei E, Jiang LX, Xu Z, Ali U, Fildes K, Cheung CY, Cook SM, Johnson DC, Bachovchin DA, Cook GM, Apte M, Huang M, Ranson M, Kelso MJ..  (2018)  6-Substituted Hexamethylene Amiloride (HMA) Derivatives as Potent and Selective Inhibitors of the Human Urokinase Plasminogen Activator for Use in Cancer.,  61  (18): [PMID:30130401] [10.1021/acs.jmedchem.8b00838]

2. Unpublished dataset, 

3. Indorf P, Kubitza C, Scheidig AJ, Kunze T, Clement B..  (2020)  Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.,  63  (12): [PMID:31790578] [10.1021/acs.jmedchem.9b01483]

Source

Source(2):

• Scientific Literature
• Clinical Candidates