3-Ethyl-2-{(E)-3-[3-ethyl-3H-benzothiazol-(2Z)-ylidene]-propenyl}-benzothiazol-3-ium iodide

ID: ALA81782

Chembl Id: CHEMBL81782

PubChem CID: 54612009

Max Phase: Preclinical

Molecular Formula: C21H21IN2S2

Molecular Weight: 365.55

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GNF-Pf-3148 | CHEBI:51895|GNF-PF-3148|CHEMBL81782

Canonical SMILES:  CCN1/C(=C/C=C/c2sc3ccccc3[n+]2CC)Sc2ccccc21.[I-]

Standard InChI:  InChI=1S/C21H21N2S2.HI/c1-3-22-16-10-5-7-12-18(16)24-20(22)14-9-15-21-23(4-2)17-11-6-8-13-19(17)25-21;/h5-15H,3-4H2,1-2H3;1H/q+1;/p-1

Standard InChI Key:  VZBILKJHDPEENF-UHFFFAOYSA-M

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: 365.55

Molecular Weight (Monoisotopic): 365.1141

AlogP: 5.70

#Rotatable Bonds: 4

Polar Surface Area: 7.12

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.99

CX LogD: 1.99

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.55

Np Likeness Score: -1.08

References

1. Kerwin SM, Sun D, Kern JT, Rangan A, Thomas PW..  (2001)  G-quadruplex DNA binding by a series of carbocyanine dyes.,  11  (18): [PMID:11549435] [10.1016/s0960-894x(01)00490-5]

2. Kawakami M, Koya K, Ukai T, Tatsuta N, Ikegawa A, Ogawa K, Shishido T, Chen LB..  (1997)  Synthesis and evaluation of novel rhodacyanine dyes that exhibit antitumor activity.,  40  (20): [PMID:9379434] [10.1021/jm9702692]

3. Chang E, Congdon EE, Honson NS, Duff KE, Kuret J..  (2009)  Structure-activity relationship of cyanine tau aggregation inhibitors.,  52  (11): [PMID:19432420] [10.1021/jm900116d]

4. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. Hu H, Owens EA, Su H, Yan L, Levitz A, Zhao X, Henary M, Zheng YG..  (2015)  Exploration of cyanine compounds as selective inhibitors of protein arginine methyltransferases: synthesis and biological evaluation.,  58  (3): [PMID:25559100] [10.1021/jm501452j]

9. Chegaev K, Federico A, Marini E, Rolando B, Fruttero R, Morbin M, Rossi G, Fugnanesi V, Bastone A, Salmona M, Badiola NB, Gasparini L, Cocco S, Ripoli C, Grassi C, Gasco A..  (2015)  NO-donor thiacarbocyanines as multifunctional agents for Alzheimer's disease.,  23  (15): [PMID:26078011] [10.1016/j.bmc.2015.05.050]

10. Iyer A, Xu W, Reid RC, Fairlie DP..  (2018)  Chemical Approaches to Modulating Complement-Mediated Diseases.,  61  (8): [PMID:28977749] [10.1021/acs.jmedchem.7b00882]

Source

Source(3):

• Scientific Literature
• Novartis Malaria Screening
• PubChem BioAssays