miravirsen   Click here for help

GtoPdb Ligand ID: 13534

Synonyms: SPC-3649 | SPC3649
Compound class: Nucleic acid
Comment: Miravirsen (SPC-3649) is a 15 mer modified antisense oligonucleotide that binds to human miR-122 [4]. This mechanism disrupts miR-122-mediated protection of viral RNA from nuclease degradation [1-3]. Miravirsen was intended for the treatment of hepatitis C infection.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1=CN(C2CC(C(COP(=S)(O)OC3C4C(N5C=NC6=C5N=CN=C6N)OC3(CO4)COP(=S)(O)OC7CC(N8C=CC(=NC8=O)N)OC7COP(=S)(O)OC9C%10C(N%11C=CC(=NC%11=O)N)OC9(CO)CO%10)O2)OP(=S)(O)OCC%12C(CC(N%13C=C(C)C(=O)NC%13=O)O%12)OP(=S)(O)OCC%14%15COC(C%14OP(=S)(O)OCC%16%17COC(C%16OP(=S)(O)OCC%18C(CC(N%19C=CC(=NC%19=O)N)O%18)OP(=S)(O)OCC%20C(CC(N%21C=NC%22=C%21N=CN=C%22N)O%20)OP(=S)(O)OCC%23%24COC(C%23OP(=S)(O)OCC%25C(CC(N%26C=NC%27=C%26N=CN=C%27N)O%25)OP(=S)(O)OCC%28%29COC(C%28OP(=S)(O)OCC%30C(CC(N%31C=C(C)C(=O)NC%31=O)O%30)OP(=S)(O)OCC%32%33COC(C%32OP(=S)(O)OCC%34%35COC(C%34O)C(N%36C=CC(=NC%36=O)N)O%35)C(N%37C=CC(=NC%37=O)N)O%33)C(N%38C=CC(=NC%38=O)N)O%29)C(N%39C=CC(=NC%39=O)N)O%24)C(N%40C=C(C)C(=O)NC%40=O)O%17)C(N%41C=NC%42=C%41N=C(N)NC%42=O)O%15)C(=O)NC1=O
Isomeric SMILES CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=S)(O)OC3C4C(OC3(CO4)COP(=S)(O)OC5CC(OC5COP(=S)(O)OC6C7C(OC6(CO7)CO)N8C=CC(=NC8=O)N)N9C=CC(=NC9=O)N)N%10C=NC%11=C(N=CN=C%11%10)N)OP(=S)(O)OCC%12C(CC(O%12)N%13C=C(C(=O)NC%13=O)C)OP(=S)(O)OCC%14%15COC(C%14OP(=S)(O)OCC%16%17COC(C%16OP(=S)(O)OCC%18C(CC(O%18)N%19C=CC(=NC%19=O)N)OP(=S)(O)OCC%20C(CC(O%20)N%21C=NC%22=C(N=CN=C%22%21)N)OP(=S)(O)OCC%23%24COC(C%23OP(=S)(O)OCC%25C(CC(O%25)N%26C=NC%27=C(N=CN=C%27%26)N)OP(=S)(O)OCC%28%29COC(C%28OP(=S)(O)OCC%30C(CC(O%30)N%31C=C(C(=O)NC%31=O)C)OP(=S)(O)OCC%32%33COC(C%32OP(=S)(O)OCC%34%35COC(C%34O)C(O%35)N%36C=CC(=NC%36=O)N)C(O%33)N%37C=CC(=NC%37=O)N)C(O%29)N%38C=CC(=NC%38=O)N)C(O%24)N%39C=CC(=NC%39=O)N)C(O%17)N%40C=C(C(=O)NC%40=O)C)C(O%15)N%41C=NC%42=C%41N=C(NC%42=O)N
InChI InChI=1S/C151H185N49O83P14S14/c1-60-26-193(140(215)182-119(60)203)87-21-66(74(258-87)34-245-290(225,304)281-110-102-130(199-58-171-94-114(161)165-55-168-117(94)199)268-150(110,44-239-102)50-252-291(226,305)272-65-20-86(187-13-6-79(153)174-134(187)209)256-72(65)33-243-286(221,300)277-105-97-125(262-144(105,37-201)38-234-97)189-15-8-81(155)176-136(189)211)271-285(220,299)241-30-73-67(22-88(257-73)194-27-61(2)120(204)183-141(194)216)273-293(228,307)253-51-151-45-240-103(131(269-151)200-59-172-95-118(200)180-132(162)181-123(95)207)111(151)283-297(232,311)254-52-149-43-238-101(129(267-149)196-29-63(4)122(206)185-143(196)218)109(149)280-289(224,303)244-32-71-64(19-85(255-71)186-12-5-78(152)173-133(186)208)270-284(219,298)242-31-76-69(24-90(260-76)197-56-169-92-112(159)163-53-166-115(92)197)275-294(229,308)249-47-147-41-236-99(127(265-147)191-17-10-83(157)178-138(191)213)107(147)279-288(223,302)247-36-77-70(25-91(261-77)198-57-170-93-113(160)164-54-167-116(93)198)276-295(230,309)250-48-146-40-235-98(126(264-146)190-16-9-82(156)177-137(190)212)106(146)278-287(222,301)246-35-75-68(23-89(259-75)195-28-62(3)121(205)184-142(195)217)274-292(227,306)251-49-148-42-237-100(128(266-148)192-18-11-84(158)179-139(192)214)108(148)282-296(231,310)248-46-145-39-233-96(104(145)202)124(263-145)188-14-7-80(154)175-135(188)210/h5-18,26-29,53-59,64-77,85-91,96-111,124-131,201-202H,19-25,30-52H2,1-4H3,(H,219,298)(H,220,299)(H,221,300)(H,222,301)(H,223,302)(H,224,303)(H,225,304)(H,226,305)(H,227,306)(H,228,307)(H,229,308)(H,230,309)(H,231,310)(H,232,311)(H2,152,173,208)(H2,153,174,209)(H2,154,175,210)(H2,155,176,211)(H2,156,177,212)(H2,157,178,213)(H2,158,179,214)(H2,159,163,166)(H2,160,164,167)(H2,161,165,168)(H,182,203,215)(H,183,204,216)(H,184,205,217)(H,185,206,218)(H3,162,180,181,207)
InChI Key OSOOBMBDIGGTCP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Hildebrandt-Eriksen ES, Aarup V, Persson R, Hansen HF, Munk ME, Ørum H. (2012)
A locked nucleic acid oligonucleotide targeting microRNA 122 is well-tolerated in cynomolgus monkeys.
Nucleic Acid Ther, 22 (3): 152-61. [PMID:22545703]
2. Lanford RE, Hildebrandt-Eriksen ES, Petri A, Persson R, Lindow M, Munk ME, Kauppinen S, Ørum H. (2010)
Therapeutic silencing of microRNA-122 in primates with chronic hepatitis C virus infection.
Science, 327 (5962): 198-201. [PMID:19965718]
3. Nunnari G, Schnell MJ. (2011)
MicroRNA-122: a therapeutic target for hepatitis C virus (HCV) infection.
Front Biosci (Schol Ed), 3 (3): 1032-7. [PMID:21622252]
4. van der Ree MH, van der Meer AJ, van Nuenen AC, de Bruijne J, Ottosen S, Janssen HL, Kootstra NA, Reesink HW. (2016)
Miravirsen dosing in chronic hepatitis C patients results in decreased microRNA-122 levels without affecting other microRNAs in plasma.
Aliment Pharmacol Ther, 43 (1): 102-13. [PMID:26503793]