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ID: ALA81782
Max Phase: Preclinical
Molecular Formula: C21H21IN2S2
Molecular Weight: 365.55
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): GNF-Pf-3148
Synonyms from Alternative Forms(1):
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
Associated Targets(Human)
CX-1 79 Activities
Telomerase reverse transcriptase 2428 Activities
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Huh-7 12904 Activities
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Ras-related protein Rab-9A 22488 Activities
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BJ 6930 Activities
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Lethal(3)malignant brain tumor-like protein 1 14536 Activities
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Niemann-Pick C1 protein 18985 Activities
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Nuclear factor erythroid 2-related factor 2 95332 Activities
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FAD-linked sulfhydryl oxidase ALR 1466 Activities
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Histone acetyltransferase GCN5 14285 Activities
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Eyes absent homolog 2 5884 Activities
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Alkaline phosphatase placental-like 1197 Activities
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ATPase family AAA domain-containing protein 5 122566 Activities
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Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 93046 Activities
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Bromodomain adjacent to zinc finger domain protein 2B 56204 Activities
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Alkaline phosphatase, tissue-nonspecific isozyme 1551 Activities
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Intestinal alkaline phosphatase 724 Activities
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Apoptotic protease-activating factor 1 1188 Activities
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Jurkat 10389 Activities
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|---|
GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 21853 Activities
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DNA polymerase iota 116820 Activities
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HepG2 196354 Activities
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DNA polymerase eta 21678 Activities
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Mothers against decapentaplegic homolog 3 68039 Activities
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Isocitrate dehydrogenase [NADP] cytoplasmic 40980 Activities
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Ataxin-2 54410 Activities
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|---|
Glucagon-like peptide 1 receptor 111429 Activities
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Werner syndrome ATP-dependent helicase 8824 Activities
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Transcriptional regulator ERG 5589 Activities
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Tyrosyl-DNA phosphodiesterase 1 345557 Activities
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TAR DNA-binding protein 43 40113 Activities
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Alpha-synuclein 10960 Activities
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Ubiquitin carboxyl-terminal hydrolase 1 22556 Activities
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Parathyroid hormone receptor 47172 Activities
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Guanine nucleotide-binding protein G(s), subunit alpha 103405 Activities
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DNA-(apurinic or apyrimidinic site) lyase 38016 Activities
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Protein-arginine N-methyltransferase 1 867 Activities
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Soluble guanylate cyclase 679 Activities
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Amyloid-beta A4 protein 8510 Activities
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Integrin alpha-M/beta-2 32 Activities
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Associated Targets(non-human)
CV-1 316 Activities
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Taq polymerase 1 482 Activities
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Plasmodium falciparum 966862 Activities
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Streptococcus 3973 Activities
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Streptococcus sp. 'group A' 3417 Activities
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Saccharomyces cerevisiae 19171 Activities
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Beta-lactamase AmpC 62480 Activities
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Streptokinase A 5805 Activities
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Intestinal alkaline phosphatase 419 Activities
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Nonstructural protein 1 33327 Activities
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Exodeoxyribonuclease V 225 Activities
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Luciferin 4-monooxygenase 66902 Activities
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T-complex protein 1 subunit beta 5007 Activities
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Phosphoglycerate kinase, glycosomal 2184 Activities
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Aberrant vpr protein 14595 Activities
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Brain 4203 Activities
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
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: 0 |
| #RO5 Violations: 1 | HBA (Lipinski): 2 | HBD (Lipinski): 0 | #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):