1,4-bis-{[N-(1-imino-1-guanidino-methyl)]sulfanylmethyl}-3,6-dimethyl-benzene

ID: ALA213969

Chembl Id: CHEMBL213969

PubChem CID: 9543473

Max Phase: Preclinical

Molecular Formula: C14H22N8S2

Molecular Weight: 366.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(CSC(=N)NC(=N)N)c(C)cc1CSC(=N)NC(=N)N

Standard InChI:  InChI=1S/C14H22N8S2/c1-7-3-10(6-24-14(20)22-12(17)18)8(2)4-9(7)5-23-13(19)21-11(15)16/h3-4H,5-6H2,1-2H3,(H5,15,16,19,21)(H5,17,18,20,22)

Standard InChI Key:  UQMGTQSCMRRWFV-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA213969

   (2,5-Dimethylbenzene-1,4-Diyl)dimethanediyl Bis(N-Carbamimidoylcarbamimidothioate)

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: 366.52

Molecular Weight (Monoisotopic): 366.1409

AlogP: 1.61

#Rotatable Bonds: 4

Polar Surface Area: 171.50

Molecular Species: BASE

HBA: 6

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.40

CX LogP: 2.68

CX LogD: -2.63

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.30

Np Likeness Score: -0.42

References

1. Summerfield RL, Daigle DM, Mayer S, Mallik D, Hughes DW, Jackson SG, Sulek M, Organ MG, Brown ED, Junop MS..  (2006)  A 2.13 A structure of E. coli dihydrofolate reductase bound to a novel competitive inhibitor reveals a new binding surface involving the M20 loop region.,  49  (24): [PMID:17125251] [10.1021/jm060570v]

2. Batruch I, Javasky E, Brown ED, Organ MG, Johnson PE..  (2010)  Thermodynamic and NMR analysis of inhibitor binding to dihydrofolate reductase.,  18  (24): [PMID:21084197] [10.1016/j.bmc.2010.10.048]

3. He J, Qiao W, An Q, Yang T, Luo Y..  (2020)  Dihydrofolate reductase inhibitors for use as antimicrobial agents.,  195  [PMID:32298876] [10.1016/j.ejmech.2020.112268]

Source

Source(1):

• Scientific Literature