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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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 121
Hydrogen bond donors 45
Rotatable bonds 96
Topological polar surface area 2147.55
Molecular weight 4610.21
XLogP -0.51
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 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/)
Classification Click here for help
Compound class Nucleic acid
Compound subclass
Target Telomerase reverse transcriptase (TERT)
Approved drug? Yes (FDA (2024))
International Nonproprietary Names Click here for help
INN number INN
9142 imetelstat
Synonyms Click here for help
GRN-163 | GRN163 | Rytelo®
Database Links Click here for help
ChEMBL Ligand CHEMBL2107856
DrugBank Ligand DB05036
GtoPdb PubChem SID 504705444
PubChem CID 72941969
Search Google for chemical match using the InChIKey LVZYXEALRXBLJZ-ISQYCPACSA-N
Search Google for chemicals with the same backbone LVZYXEALRXBLJZ
Search PubMed clinical trials imetelstat
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Search PubMed titles/abstracts imetelstat
UniChem Compound Search for chemical match using the InChIKey LVZYXEALRXBLJZ-ISQYCPACSA-N
UniChem Connectivity Search for chemical match using the InChIKey LVZYXEALRXBLJZ-ISQYCPACSA-N