Suramin

ID: ALA3040216

Chembl Id: CHEMBL3040216

PubChem CID: 73355036

Max Phase: Preclinical

Molecular Formula: C51H40N6O23S6

Molecular Weight: 1297.30

Molecule Type: Unknown

Associated Items:

Names and Identifiers

Canonical SMILES:  CC1=CCC(C(=O)/N=C2\CC=C(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c32)=C/C1=N/C(=O)C1=CC=C/C(=N\C(=O)/N=C2\C=CC=C(C(=O)/N=C3/CC(C(=O)/N=C4\CC=C(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c54)=CC=C3C)C2)C1

Standard InChI:  InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-11,15-16,20-24H,12-14,17-19H2,1-2H3,(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80)/b52-31+,53-32+,54-37+,55-38+,56-39-,57-40-

Standard InChI Key:  VTCUUTNDNRAQSK-NCNWUEASSA-N

Associated Targets(Human)

PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HUVEC (11049 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENPP1 Tchem Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 (635 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSNAX Tbio Translin-associated protein X (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSPD1 Tbio HSP60/HSP10 (366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CISD1 Tchem CDGSH iron-sulfur domain-containing protein 1 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIRT1 Tchem NAD-dependent deacetylase sirtuin 1 (3505 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIRT2 Tchem NAD-dependent deacetylase sirtuin 2 (3979 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIRT3 Tchem NAD-dependent deacetylase sirtuin 3 (1285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENPP3 Tchem Ectonucleotide pyrophosphatase/phosphodiesterase family member 3 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENTPD1 Tchem Ectonucleoside triphosphate diphosphohydrolase 1 (116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENTPD2 Tchem Ectonucleoside triphosphate diphosphohydrolase 2 (116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENTPD3 Tchem Ectonucleoside triphosphate diphosphohydrolase 3 (108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ENTPD8 Tbio Ectonucleoside triphosphate diphosphohydrolase 8 (96 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX7 Tchem Chromobox protein homolog 7 (354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX3 Tclin P2X purinoceptor 3 (1991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX1 Tchem P2X purinoceptor 1 (328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX2 Tchem P2X purinoceptor 2 (190 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX4 Tchem P2X purinoceptor 4 (516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPSE Tchem Heparanase (634 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PCSK9 Tclin Subtilisin/kexin type 9 (362 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TST Tchem Thiosulfate sulfurtransferase (144 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MRC5 (9203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP2 Tchem Tyrosyl-DNA phosphodiesterase 2 (864 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIRT5 Tchem NAD-dependent protein deacylase sirtuin-5, mitochondrial (1056 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FGF1 Tchem Fibroblast growth factor 1/Fibroblast growth factor receptor 2 (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FHIT Tchem Bis(5'-adenosyl)-triphosphatase (95 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX5 Tchem P2X purinoceptor 5 (52 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX7 Tchem P2X purinoceptor 7 (5534 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGO2 Tbio Protein argonaute-2 (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
groL GroEL/GroES (1042 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hpse Heparanase (2 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei (78846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SIR2RP1 Putative silent information regulator 2 (21 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enpp1 Ectonucleotide pyrophosphatase/phosphodiesterase family member 1 (7 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zika virus (1028 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
groEL 60 kDa chaperonin (64 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dengue virus type 2 NS3 protein (2214 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dengue virus type 2 (2400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2rx1 P2X purinoceptor 1 (52 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NS3 Genome polyprotein (385 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Entpd1 Ectonucleoside triphosphate diphosphohydrolase 1 (6 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei gambiense (523 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma congolense (178 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma evansi (198 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PYK Pyruvate kinase (6726 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chikungunya virus (1339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 1297.30Molecular Weight (Monoisotopic): 1296.0469AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

References

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18. Gudisela MR, Srinivasu N, Mulakayala C, Bommu P, Rao MVB, Mulakayala N..  (2017)  Design, synthesis and anticancer activity of N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl derivatives.,  27  (17): [PMID:28756024] [10.1016/j.bmcl.2017.07.029]
19. Zheng HC, Lu Y, Chen DF..  (2018)  Anticomplement compounds from Polygonum chinense.,  28  (9): [PMID:29631958] [10.1016/j.bmcl.2018.03.079]
20. Kuhrt D, Ejaz SA, Afzal S, Khan SU, Lecka J, Sévigny J, Ehlers P, Spannenberg A, Iqbal J, Langer P..  (2017)  Chemoselective synthesis and biological evaluation of arylated 2-(Trifluoromethyl) quinolines as nucleotide pyrophosphatase (NPPs) inhibitors.,  138  [PMID:28735213] [10.1016/j.ejmech.2017.07.017]
21. Teske KA, Hadden MK..  (2017)  Methyllysine binding domains: Structural insight and small molecule probe development.,  136  [PMID:28478342] [10.1016/j.ejmech.2017.04.047]
22. Venkatraj M, Salado IG, Heeres J, Joossens J, Lewi PJ, Caljon G, Maes L, Van der Veken P, Augustyns K..  (2018)  Novel triazine dimers with potent antitrypanosomal activity.,  143  [PMID:29197735] [10.1016/j.ejmech.2017.11.075]
23. Kim TK, Kim JE, Youn UJ, Han SJ, Kim IC, Cho CG, Yim JH..  (2018)  Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum.,  81  (6): [PMID:29878768] [10.1021/acs.jnatprod.8b00227]
24. Kwak SH, Shin S, Lee JH, Shim JK, Kim M, Lee SD, Lee A, Bae J, Park JH, Abdelrahman A, Müller CE, Cho SK, Kang SG, Bae MA, Yang JY, Ko H, Goddard WA, Kim YC..  (2018)  Synthesis and structure-activity relationships of quinolinone and quinoline-based P2X7 receptor antagonists and their anti-sphere formation activities in glioblastoma cells.,  151  [PMID:29649742] [10.1016/j.ejmech.2018.03.023]
25. Pedron J, Boudot C, Hutter S, Bourgeade-Delmas S, Stigliani JL, Sournia-Saquet A, Moreau A, Boutet-Robinet E, Paloque L, Mothes E, Laget M, Vendier L, Pratviel G, Wyllie S, Fairlamb A, Azas N, Courtioux B, Valentin A, Verhaeghe P..  (2018)  Novel 8-nitroquinolin-2(1H)-ones as NTR-bioactivated antikinetoplastid molecules: Synthesis, electrochemical and SAR study.,  155  [PMID:29885575] [10.1016/j.ejmech.2018.06.001]
26. Rondanin R, Fochi S, Baruchello R, Bernardi T, Oliva P, Semeraro F, Simoni D, Giannini G..  (2017)  Arylamidonaphtalene sulfonate compounds as a novel class of heparanase inhibitors.,  27  (18): [PMID:28811133] [10.1016/j.bmcl.2017.08.013]
27. Blaazer AR, Singh AK, de Heuvel E, Edink E, Orrling KM, Veerman JJN, van den Bergh T, Jansen C, Balasubramaniam E, Mooij WJ, Custers H, Sijm M, Tagoe DNA, Kalejaiye TD, Munday JC, Tenor H, Matheeussen A, Wijtmans M, Siderius M, de Graaf C, Maes L, de Koning HP, Bailey DS, Sterk GJ, de Esch IJP, Brown DG, Leurs R..  (2018)  Targeting a Subpocket in Trypanosoma brucei Phosphodiesterase B1 (TbrPDEB1) Enables the Structure-Based Discovery of Selective Inhibitors with Trypanocidal Activity.,  61  (9): [PMID:29672041] [10.1021/acs.jmedchem.7b01670]
28. Hailu GS, Robaa D, Forgione M, Sippl W, Rotili D, Mai A..  (2017)  Lysine Deacetylase Inhibitors in Parasites: Past, Present, and Future Perspectives.,  60  (12): [PMID:28241112] [10.1021/acs.jmedchem.6b01595]
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31. Zhang H, Collins J, Nyamwihura R, Ware S, Kaiser M, Ogungbe IV..  (2018)  Discovery of a quinoline-based phenyl sulfone derivative as an antitrypanosomal agent.,  28  (9): [PMID:29609908] [10.1016/j.bmcl.2018.03.039]
32. Salado IG, Baán A, Verdeyen T, Matheeussen A, Caljon G, Van der Veken P, Kiekens F, Maes L, Augustyns K..  (2018)  Optimization of the pharmacokinetic properties of potent anti-trypanosomal triazine derivatives.,  151  [PMID:29604541] [10.1016/j.ejmech.2018.03.048]
33. Cogo J, Cantizani J, Cotillo I, Sangi DP, Corrêa AG, Ueda-Nakamura T, Filho BPD, Martín JJ, Nakamura CV..  (2018)  Quinoxaline derivatives as potential antitrypanosomal and antileishmanial agents.,  26  (14): [PMID:30100019] [10.1016/j.bmc.2018.06.033]
34. West RA, O'Doherty OG, Askwith T, Atack J, Beswick P, Laverick J, Paradowski M, Pennicott LE, Rao SPS, Williams G, Ward SE..  (2017)  African trypanosomiasis: Synthesis & SAR enabling novel drug discovery of ubiquinol mimics for trypanosome alternative oxidase.,  141  [PMID:29107420] [10.1016/j.ejmech.2017.09.067]
35. Lee SY, Müller CE..  (2017)  Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) and its inhibitors.,  (5): [PMID:30108800] [10.1039/C7MD00015D]
36. Woodring JL, Behera R, Sharma A, Wiedeman J, Patel G, Singh B, Guyett P, Amata E, Erath J, Roncal N, Penn E, Leed SE, Rodriguez A, Sciotti RJ, Mensa-Wilmot K, Pollastri MP..  (2018)  Series of Alkynyl-Substituted Thienopyrimidines as Inhibitors of Protozoan Parasite Proliferation.,  (10): [PMID:30344906] [10.1021/acsmedchemlett.8b00245]
37. Channar PA, Afzal S, Ejaz SA, Saeed A, Larik FA, Mahesar PA, Lecka J, Sévigny J, Erben MF, Iqbal J..  (2018)  Exploration of carboxy pyrazole derivatives: Synthesis, alkaline phosphatase, nucleotide pyrophosphatase/phosphodiesterase and nucleoside triphosphate diphosphohydrolase inhibition studies with potential anticancer profile.,  156  [PMID:30015078] [10.1016/j.ejmech.2018.07.002]
38. Fersing C, Boudot C, Pedron J, Hutter S, Primas N, Castera-Ducros C, Bourgeade-Delmas S, Sournia-Saquet A, Moreau A, Cohen A, Stigliani JL, Pratviel G, Crozet MD, Wyllie S, Fairlamb A, Valentin A, Rathelot P, Azas N, Courtioux B, Verhaeghe P, Vanelle P..  (2018)  8-Aryl-6-chloro-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridines as potent antitrypanosomatid molecules bioactivated by type 1 nitroreductases.,  157  [PMID:30092366] [10.1016/j.ejmech.2018.07.064]
39. El-Gamal MI, Ullah S, Zaraei SO, Jalil S, Zaib S, Zaher DM, Omar HA, Anbar HS, Pelletier J, Sévigny J, Iqbal J..  (2019)  Synthesis, biological evaluation, and docking studies of new raloxifene sulfonate or sulfamate derivatives as inhibitors of nucleotide pyrophosphatase/phosphodiesterase.,  181  [PMID:31382118] [10.1016/j.ejmech.2019.07.063]
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