inotersen   Click here for help

GtoPdb Ligand ID: 13543

Synonyms: GSK-2998728 | GSK2998728 | ISIS-420915 | ISIS420915 | Tegsedi®
Approved drug
inotersen is an approved drug (EMA & FDA (2018), UK MHRA (2021))
Compound class: Nucleic acid
Comment: Inotersen is an antisense oligonucleotide that blocks expression of mutant transthyretin (TTR) protein that form pathogenic deposits in patients with hereditary transthyretin-mediated amyloidosis (hATTR).
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 190
Hydrogen bond donors 44
Rotatable bonds 156
Topological polar surface area 3161.13
Molecular weight 7183.14
XLogP -12.77
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
Click here for help

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/)

✖
Canonical SMILES CC1=CN([C@H]2C[C@@H]([C@@H](COP(=S)(O)O[C@H]3C[C@H](N4C=NC5=C4N=CN=C5N)O[C@@H]3COP(=S)(O)O[C@H]6C[C@H](N7C=C(C)C(=O)NC7=O)O[C@@H]6COP(=S)(O)O[C@H]8C[C@H](N9C=C(C)C(=O)NC9=O)O[C@@H]8COP(=S)(O)O[C@H]%10C[C@H](N%11C=NC%12=C%11N=C(N)NC%12=O)O[C@@H]%10COP(=S)(O)O[C@@H]%13[C@@H](COP(=S)(O)O[C@@H]%14[C@@H](COP(=S)(O)O[C@@H]%15[C@@H](COP(=S)(O)O[C@@H]%16[C@@H](COP(=S)(O)O[C@@H]%17[C@@H](CO)O[C@H]([C@@H]%17OCCOC)N%18C=C(C)C(=O)NC%18=O)O[C@H]([C@@H]%16OCCOC)N%19C=C(C)C(=NC%19=O)N)O[C@H]([C@@H]%15OCCOC)N%20C=C(C)C(=O)NC%20=O)O[C@H]([C@@H]%14OCCOC)N%21C=C(C)C(=O)NC%21=O)O[C@H]([C@@H]%13OCCOC)N%22C=NC%23=C%22N=C(N)NC%23=O)O2)OP(=S)(O)OC[C@@H]%24[C@H](C[C@H](N%25C=NC%26=C%25N=CN=C%26N)O%24)OP(=S)(O)OC[C@@H]%27[C@H](C[C@H](N%28C=C(C)C(=O)NC%28=O)O%27)OP(=S)(O)OC[C@@H]%29[C@H](C[C@H](N%30C=NC%31=C%30N=C(N)NC%31=O)O%29)OP(=S)(O)OC[C@@H]%32[C@H](C[C@H](N%33C=NC%34=C%33N=CN=C%34N)O%32)OP(=S)(O)OC[C@@H]%35[C@H](C[C@H](N%36C=NC%37=C%36N=CN=C%37N)O%35)OP(=S)(O)OC[C@@H]%38[C@H]([C@H]([C@H](N%39C=NC%40=C%39N=CN=C%40N)O%38)OCCOC)OP(=S)(O)OC[C@@H]%41[C@H]([C@H]([C@H](N%42C=C(C)C(=O)NC%42=O)O%41)OCCOC)OP(=S)(O)OC[C@@H]%43[C@H]([C@H]([C@H](N%44C=C(C)C(=NC%44=O)N)O%43)OCCOC)OP(=S)(O)OC[C@@H]%45[C@H]([C@H]([C@H](N%46C=C(C)C(=NC%46=O)N)O%45)OCCOC)OP(=S)(O)OC[C@@H]%47[C@H]([C@H]([C@H](N%48C=C(C)C(=NC%48=O)N)O%47)OCCOC)O)C(=O)N=C1N
Isomeric SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=S)(O)O[C@H]3C[C@@H](O[C@@H]3COP(=S)(O)O[C@H]4C[C@@H](O[C@@H]4COP(=S)(O)O[C@@H]5[C@H](O[C@H]([C@@H]5OCCOC)N6C=NC7=C6N=C(NC7=O)N)COP(=S)(O)O[C@@H]8[C@H](O[C@H]([C@@H]8OCCOC)N9C=C(C(=O)NC9=O)C)COP(=S)(O)O[C@@H]%10[C@H](O[C@H]([C@@H]%10OCCOC)N%11C=C(C(=O)NC%11=O)C)COP(=S)(O)O[C@@H]%12[C@H](O[C@H]([C@@H]%12OCCOC)N%13C=C(C(=NC%13=O)N)C)COP(=S)(O)O[C@@H]%14[C@H](O[C@H]([C@@H]%14OCCOC)N%15C=C(C(=O)NC%15=O)C)CO)N%16C=NC%17=C%16N=C(NC%17=O)N)N%18C=C(C(=O)NC%18=O)C)OP(=S)(O)OC[C@@H]%19[C@H](C[C@@H](O%19)N%20C=NC%21=C(N=CN=C%21%20)N)OP(=S)(O)OC[C@@H]%22[C@H](C[C@@H](O%22)N%23C=C(C(=NC%23=O)N)C)OP(=S)(O)OC[C@@H]%24[C@H](C[C@@H](O%24)N%25C=NC%26=C(N=CN=C%26%25)N)OP(=S)(O)OC[C@@H]%27[C@H](C[C@@H](O%27)N%28C=C(C(=O)NC%28=O)C)OP(=S)(O)OC[C@@H]%29[C@H](C[C@@H](O%29)N%30C=NC%31=C%30N=C(NC%31=O)N)OP(=S)(O)OC[C@@H]%32[C@H](C[C@@H](O%32)N%33C=NC%34=C(N=CN=C%34%33)N)OP(=S)(O)OC[C@@H]%35[C@H](C[C@@H](O%35)N%36C=NC%37=C(N=CN=C%37%36)N)OP(=S)(O)OC[C@@H]%38[C@H]([C@H]([C@@H](O%38)N%39C=NC%40=C(N=CN=C%40%39)N)OCCOC)OP(=S)(O)OC[C@@H]%41[C@H]([C@H]([C@@H](O%41)N%42C=C(C(=O)NC%42=O)C)OCCOC)OP(=S)(O)OC[C@@H]%43[C@H]([C@H]([C@@H](O%43)N%44C=C(C(=NC%44=O)N)C)OCCOC)OP(=S)(O)OC[C@@H]%45[C@H]([C@H]([C@@H](O%45)N%46C=C(C(=NC%46=O)N)C)OCCOC)OP(=S)(O)OC[C@@H]%47[C@H]([C@H]([C@@H](O%47)N%48C=C(C(=NC%48=O)N)C)OCCOC)O
InChI InChI=1S/C230H318N69O121P19S19/c1-98-53-280(219(312)262-178(98)231)140-43-110(121(382-140)66-364-425(328,444)406-114-47-144(292-90-254-150-183(236)244-85-249-188(150)292)387-126(114)71-368-423(326,442)404-112-45-142(282-59-104(7)197(303)274-225(282)318)383-122(112)67-363-421(324,440)403-111-44-141(281-58-103(6)196(302)273-224(281)317)385-124(111)69-366-427(330,446)410-119-52-149(297-95-260-156-194(297)268-217(242)271-204(156)310)391-130(119)75-372-431(334,450)419-167-139(401-215(177(167)362-42-32-352-22)299-97-261-157-195(299)269-218(243)272-205(157)311)84-381-438(341,457)418-165-136(398-213(175(165)360-40-30-350-20)291-64-109(12)202(308)279-230(291)323)82-379-437(340,456)417-163-135(397-211(173(163)358-38-28-348-18)289-62-107(10)200(306)277-228(289)321)81-378-435(338,454)414-161-132(394-209(171(161)356-36-26-346-16)286-56-101(4)181(234)265-222(286)315)78-375-433(336,452)412-159-120(65-300)392-207(169(159)354-34-24-344-14)288-61-106(9)199(305)276-227(288)320)402-422(325,441)367-70-125-115(48-145(386-125)293-91-255-151-184(237)245-86-250-189(151)293)407-426(329,445)365-68-123-113(46-143(384-123)283-60-105(8)198(304)275-226(283)319)405-424(327,443)371-74-129-118(51-148(390-129)296-94-259-155-193(296)267-216(241)270-203(155)309)409-429(332,448)370-72-127-116(49-146(388-127)294-92-256-152-185(238)246-87-251-190(152)294)408-428(331,447)369-73-128-117(50-147(389-128)295-93-257-153-186(239)247-88-252-191(153)295)411-430(333,449)374-77-138-166(176(361-41-31-351-21)214(400-138)298-96-258-154-187(240)248-89-253-192(154)298)420-439(342,458)380-83-137-164(174(359-39-29-349-19)212(399-137)290-63-108(11)201(307)278-229(290)322)416-436(339,455)377-80-134-162(172(357-37-27-347-17)210(396-134)287-57-102(5)182(235)266-223(287)316)415-434(337,453)376-79-133-160(170(355-35-25-345-15)208(395-133)285-55-100(3)180(233)264-221(285)314)413-432(335,451)373-76-131-158(301)168(353-33-23-343-13)206(393-131)284-54-99(2)179(232)263-220(284)313/h53-64,85-97,110-149,158-177,206-215,300-301H,23-52,65-84H2,1-22H3,(H,324,440)(H,325,441)(H,326,442)(H,327,443)(H,328,444)(H,329,445)(H,330,446)(H,331,447)(H,332,448)(H,333,449)(H,334,450)(H,335,451)(H,336,452)(H,337,453)(H,338,454)(H,339,455)(H,340,456)(H,341,457)(H,342,458)(H2,231,262,312)(H2,232,263,313)(H2,233,264,314)(H2,234,265,315)(H2,235,266,316)(H2,236,244,249)(H2,237,245,250)(H2,238,246,251)(H2,239,247,252)(H2,240,248,253)(H,273,302,317)(H,274,303,318)(H,275,304,319)(H,276,305,320)(H,277,306,321)(H,278,307,322)(H,279,308,323)(H3,241,267,270,309)(H3,242,268,271,310)(H3,243,269,272,311)/t110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120+,121+,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,132+,133+,134+,135+,136+,137+,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148+,149+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,206+,207+,208+,209+,210+,211+,212+,213+,214+,215+,421?,422?,423?,424?,425?,426?,427?,428?,429?,430?,431?,432?,433?,434?,435?,436?,437?,438?,439?/m0/s1
InChI Key KLEGMTRDCCDFJK-XDQSQZFTSA-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 Transthyretin (TTR)
Approved drug? Yes (EMA & FDA (2018), UK MHRA (2021))
IUPAC Name Click here for help
Thy-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-Gua-MeOEt(-2)Ribf-sP-dGuo-sP-dThd-sP-dThd-sP-dAdo-sP-m5Cyt-dRibf-sP-dAdo-sP-dThd-sP-dGuo-sP-dAdo-sP-dAdo-sP-Ade-MeOEt(-2)Ribf-sP-Thy-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf-sP-m5Cyt-MeOEt(-2)Ribf
International Nonproprietary Names Click here for help
INN number INN
10294 inotersen
Synonyms Click here for help
GSK-2998728 | GSK2998728 | ISIS-420915 | ISIS420915 | Tegsedi®
Database Links Click here for help
CAS Registry No. 1492984-65-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297770
DrugBank Ligand DB14713
GtoPdb PubChem SID 500839953
PubChem CID 121493437
Search Google for chemical match using the InChIKey KLEGMTRDCCDFJK-XDQSQZFTSA-N
Search Google for chemicals with the same backbone KLEGMTRDCCDFJK
Search PubMed clinical trials inotersen
Search PubMed titles inotersen
Search PubMed titles/abstracts inotersen
UniChem Compound Search for chemical match using the InChIKey KLEGMTRDCCDFJK-XDQSQZFTSA-N
UniChem Connectivity Search for chemical match using the InChIKey KLEGMTRDCCDFJK-XDQSQZFTSA-N