imetelstat   Click here for help

GtoPdb Ligand ID: 13625

Synonyms: GRN-163 | GRN163 | Rytelo®
Approved drug
imetelstat is an approved drug (FDA (2024))
Compound class: Nucleic acid
Comment: Imetelstat is a lipid (palmitoyl) conjugated thio-phosphoramidate oligonucleotide-based telomerase (TERT) inhibitor [1]. It binds competitively to the RNA template region of the enzyme and blocks its catalytic action and its interaction with telomeres [3]. It was developed for the treatment of myeloid hematologic malignancies.
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 CCCCCCCCCCCCCCCC(=O)NCC(COP(=S)(O)OC[C@@H]1[C@H](C[C@H](N2C=C(C)C(=O)NC2=O)O1)NP(=S)(O)OC[C@@H]3[C@H](C[C@H](N4C=NC5=C4N=CN=C5N)O3)NP(=S)(O)OC[C@@H]6[C@H](C[C@H](N7C=NC8=C7N=C(N)NC8=O)O6)NP(=S)(O)OC[C@@H]9[C@H](C[C@H](N%10C=NC%11=C%10N=C(N)NC%11=O)O9)NP(=S)(O)OC[C@@H]%12[C@H](C[C@H](N%13C=NC%14=C%13N=C(N)NC%14=O)O%12)NP(=S)(O)OC[C@@H]%15[C@H](C[C@H](N%16C=C(C)C(=O)NC%16=O)O%15)NP(=S)(O)OC[C@@H]%17[C@H](C[C@H](N%18C=C(C)C(=O)NC%18=O)O%17)NP(=S)(O)OC[C@@H]%19[C@H](C[C@H](N%20C=NC%21=C%20N=CN=C%21N)O%19)NP(=S)(O)OC[C@@H]%22[C@H](C[C@H](N%23C=NC%24=C%23N=C(N)NC%24=O)O%22)NP(=S)(O)OC[C@@H]%25[C@H](C[C@H](N%26C=NC%27=C%26N=CN=C%27N)O%25)NP(=S)(O)OC[C@@H]%28[C@H](C[C@H](N%29C=CC(=NC%29=O)N)O%28)NP(=S)(O)OC[C@@H]%30[C@H](C[C@H](N%31C=NC%32=C%31N=CN=C%32N)O%30)NP(=S)(O)OC[C@@H]%33[C@H](C[C@H](N%34C=NC%35=C%34N=CN=C%35N)O%33)N)O
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)NCC(COP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)C)NP(=S)(O)OC[C@@H]3[C@H](C[C@@H](O3)N4C=NC5=C(N=CN=C54)N)NP(=S)(O)OC[C@@H]6[C@H](C[C@@H](O6)N7C=NC8=C7N=C(NC8=O)N)NP(=S)(O)OC[C@@H]9[C@H](C[C@@H](O9)N%10C=NC%11=C%10N=C(NC%11=O)N)NP(=S)(O)OC[C@@H]%12[C@H](C[C@@H](O%12)N%13C=NC%14=C%13N=C(NC%14=O)N)NP(=S)(O)OC[C@@H]%15[C@H](C[C@@H](O%15)N%16C=C(C(=O)NC%16=O)C)NP(=S)(O)OC[C@@H]%17[C@H](C[C@@H](O%17)N%18C=C(C(=O)NC%18=O)C)NP(=S)(O)OC[C@@H]%19[C@H](C[C@@H](O%19)N%20C=NC%21=C(N=CN=C%21%20)N)NP(=S)(O)OC[C@@H]%22[C@H](C[C@@H](O%22)N%23C=NC%24=C%23N=C(NC%24=O)N)NP(=S)(O)OC[C@@H]%25[C@H](C[C@@H](O%25)N%26C=NC%27=C(N=CN=C%27%26)N)NP(=S)(O)OC[C@@H]%28[C@H](C[C@@H](O%28)N%29C=CC(=NC%29=O)N)NP(=S)(O)OC[C@@H]%30[C@H](C[C@@H](O%30)N%31C=NC%32=C(N=CN=C%32%31)N)NP(=S)(O)OC[C@@H]%33[C@H](C[C@@H](O%33)N%34C=NC%35=C(N=CN=C%35%34)N)N)O
InChI InChI=1S/C148H211N68O53P13S13/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-97(218)160-34-69(217)38-255-282(242,295)256-51-95-74(25-102(261-95)207-37-68(4)136(221)191-148(207)229)195-274(234,287)249-45-89-78(29-106(264-89)212-61-175-115-124(155)165-56-170-129(115)212)199-277(237,290)252-48-92-81(32-109(267-92)215-64-178-118-132(215)183-143(158)187-139(118)224)202-280(240,293)254-50-94-82(33-110(269-94)216-65-179-119-133(216)184-144(159)188-140(119)225)203-281(241,294)253-49-93-79(30-107(268-93)213-62-176-116-130(213)181-141(156)185-137(116)222)200-278(238,291)246-42-86-72(23-100(260-86)205-35-66(2)134(219)189-146(205)227)193-272(232,285)245-41-85-73(24-101(259-85)206-36-67(3)135(220)190-147(206)228)194-273(233,286)248-44-88-77(28-105(263-88)211-60-174-114-123(154)164-55-169-128(114)211)198-276(236,289)251-47-91-80(31-108(266-91)214-63-177-117-131(214)182-142(157)186-138(117)223)201-279(239,292)250-46-90-76(27-104(265-90)210-59-173-113-122(153)163-54-168-127(113)210)197-275(235,288)244-40-84-71(22-99(258-84)204-20-19-96(150)180-145(204)226)192-271(231,284)247-43-87-75(26-103(262-87)209-58-172-112-121(152)162-53-167-126(112)209)196-270(230,283)243-39-83-70(149)21-98(257-83)208-57-171-111-120(151)161-52-166-125(111)208/h19-20,35-37,52-65,69-95,98-110,217H,5-18,21-34,38-51,149H2,1-4H3,(H,160,218)(H,242,295)(H2,150,180,226)(H2,151,161,166)(H2,152,162,167)(H2,153,163,168)(H2,154,164,169)(H2,155,165,170)(H,189,219,227)(H,190,220,228)(H,191,221,229)(H2,192,231,284)(H2,193,232,285)(H2,194,233,286)(H2,195,234,287)(H2,196,230,283)(H2,197,235,288)(H2,198,236,289)(H2,199,237,290)(H2,200,238,291)(H2,201,239,292)(H2,202,240,293)(H2,203,241,294)(H3,156,181,185,222)(H3,157,182,186,223)(H3,158,183,187,224)(H3,159,184,188,225)/t69?,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83+,84+,85+,86+,87+,88+,89+,90+,91+,92+,93+,94+,95+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,109+,110+,270?,271?,272?,273?,274?,275?,276?,277?,278?,279?,280?,281?,282?/m0/s1
InChI Key LVZYXEALRXBLJZ-ISQYCPACSA-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/)
Nucleic Acid Sequence Click here for help
(3'-5')d(3'-amino-3'-deoxy-P-thio)(AGGGTTAGACAA)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel