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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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were 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/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 132
Hydrogen bond donors 32
Rotatable bonds 86
Topological polar surface area 2271.58
Molecular weight 4896.93
XLogP -11.34
No. Lipinski's rules broken 4

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/)
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/)
Classification Click here for help
Compound class Nucleic acid
Compound subclass Antisense oligonucleotide (ASO)
Target microRNA 122
International Nonproprietary Names Click here for help
INN number INN
9168 miravirsen
Synonyms Click here for help
SPC-3649 | SPC3649
Database Links Click here for help
CAS Registry No. 1072874-90-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL2108360
DrugBank Ligand DB12851
GtoPdb PubChem SID 500839944
PubChem CID 56843415
Search Google for chemical match using the InChIKey OSOOBMBDIGGTCP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OSOOBMBDIGGTCP
Search PubMed clinical trials miravirsen
Search PubMed titles miravirsen
Search PubMed titles/abstracts miravirsen
UniChem Compound Search for chemical match using the InChIKey OSOOBMBDIGGTCP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OSOOBMBDIGGTCP-UHFFFAOYSA-N