cenersen   Click here for help

GtoPdb Ligand ID: 8270

Synonyms: Aezea® (proposed proprietary name) | EL625
Compound class: Synthetic organic
Comment: Cenersen is a 20mer phosphorothioate antisense oligonucleotide complementary to a region of p53 messenger RNA [1]. The oligonucleotide sequence is reported as 5′-d[P-Thio](ccctgctccc ccctggctcc)-3′ [1]. This sequence matches nucleotides 1273-1292 of RefSeq nucleotide NM_000546 (Homo sapiens tumor protein p53 (TP53), transcript variant 1, mRNA).

HELM notation for the nucleotide sequence is: RNA1{[dR](C).[sp][dR](G).[sp][dR](G).[sp][dR](C).[sp][dR](A).[sp][dR](T).[sp][dR](G).[sp][dR](T).[sp][dR](C).[sp][dR](T).[sp][dR](C).[sp][dR](T).[sp][dR](C).[sp][dR](T).[sp][dR](T).[sp][dR](G).[sp][dR](C).[sp][mR](A).[sp][mR](C).[sp][mR](C)}$$$$
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 CDK toolkit. 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 172
Hydrogen bond donors 57
Rotatable bonds 119
Topological polar surface area 3047.76
Molecular weight 6415.24
XLogP 12.52
No. Lipinski's rules broken 5
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.

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Canonical SMILES CC1=CN(C2CC(C(COP(=S)(O)OC3CC(N4C=CC(=N)N=C4O)OC3COP(=S)(O)OC5CC(N6C=C(C)C(=NC6=O)O)OC5COP(=S)(O)OC7CC(N8C=NC9=C8NC(=N)N=C9O)OC7COP(=S)(O)OC%10CC(N%11C=C(C)C(=NC%11=O)O)OC%10COP(=S)(O)OC%12CC(N%13C=NC%14=C%13N=CN=C%14N)OC%12COP(=S)(O)OC%15CC(N%16C=CC(=N)N=C%16O)OC%15COP(=S)(O)OC%17CC(N%18C=NC%19=C%18NC(=N)N=C%19O)OC%17COP(=S)(O)OC%20CC(N%21C=NC%22=C%21NC(=N)N=C%22O)OC%20COP(=S)(O)OC%23CC(N%24C=CC(=N)N=C%24O)OC%23CO)O2)OP(=S)(O)OCC%25C(CC(N%26C=CC(=N)N=C%26O)O%25)OP(=S)(O)OCC%27C(CC(N%28C=C(C)C(=NC%28=O)O)O%27)OP(=S)(O)OCC%29C(CC(N%30C=CC(=N)N=C%30O)O%29)OP(=S)(O)OCC%31C(CC(N%32C=C(C)C(=NC%32=O)O)O%31)OP(=S)(O)OCC%33C(CC(N%34C=C(C)C(=NC%34=O)O)O%33)OP(=S)(O)OCC%35C(CC(N%36C=NC%37=C%36NC(=N)N=C%37O)O%35)OP(=S)(O)OCC%38C(CC(N%39C=CC(=N)N=C%39O)O%38)OP(=S)(O)OCC%40C(C(C(N%41C=NC%42=C%41N=CN=C%42N)O%40)OC)OP(=S)(O)OCC%43C(C(C(N%44C=CC(=N)N=C%44O)O%43)OC)OP(=S)(O)OCC%45C(C(C(N%46C=CC(=N)N=C%46O)O%45)OC)O)C(=O)N=C1O
Isomeric SMILES CC1=CN(C(=O)N=C1O)C2CC(C(O2)COP(=S)(O)OC3CC(OC3COP(=S)(O)OC4CC(OC4COP(=S)(O)OC5CC(OC5COP(=S)(O)OC6CC(OC6COP(=S)(O)OC7CC(OC7COP(=S)(O)OC8CC(OC8COP(=S)(O)OC9CC(OC9COP(=S)(O)OC%10CC(OC%10COP(=S)(O)OC%11CC(OC%11COP(=S)(O)OC%12CC(OC%12COP(=S)(O)OC%13CC(OC%13CO)N%14C=CC(=N)N=C%14O)N%15C=NC%16=C%15NC(=N)N=C%16O)N%17C=NC%18=C%17NC(=N)N=C%18O)N%19C=CC(=N)N=C%19O)N%20C=NC%21=C(N=CN=C%21%20)N)N%22C=C(C(=NC%22=O)O)C)N%23C=NC%24=C%23NC(=N)N=C%24O)N%25C=C(C(=NC%25=O)O)C)N%26C=CC(=N)N=C%26O)N%27C=C(C(=NC%27=O)O)C)N%28C=CC(=N)N=C%28O)OP(=S)(O)OCC%29C(CC(O%29)N%30C=CC(=N)N=C%30O)OP(=S)(O)OCC%31C(CC(O%31)N%32C=C(C(=NC%32=O)O)C)OP(=S)(O)OCC%33C(CC(O%33)N%34C=C(C(=NC%34=O)O)C)OP(=S)(O)OCC%35C(CC(O%35)N%36C=NC%37=C%36NC(=N)N=C%37O)OP(=S)(O)OCC%38C(CC(O%38)N%39C=CC(=N)N=C%39O)OP(=S)(O)OCC%40C(C(C(O%40)N%41C=NC%42=C(N=CN=C%42%41)N)OC)OP(=S)(O)OCC%43C(C(C(O%43)N%44C=CC(=N)N=C%44O)OC)OP(=S)(O)OCC%45C(C(C(O%45)N%46C=CC(=N)N=C%46O)OC)O
InChI InChI=1S/C195H253N66O106P19S19/c1-77-43-250(190(282)236-165(77)264)134-32-89(107(336-134)56-317-370(290,389)351-85-28-130(244-20-12-122(198)222-184(244)276)332-103(85)52-313-375(295,394)357-91-34-136(252-45-79(3)167(266)238-192(252)284)340-111(91)60-321-382(302,401)364-99-42-144(260-75-219-150-164(260)231-181(209)235-174(150)273)344-115(99)64-324-378(298,397)360-94-37-139(255-48-82(6)170(269)241-195(255)287)339-110(94)59-320-381(301,400)361-95-38-140(256-71-214-145-157(204)210-69-212-159(145)256)341-112(95)61-322-372(292,391)353-87-30-132(246-22-14-124(200)224-186(246)278)333-104(87)53-314-379(299,398)363-98-41-143(259-74-218-149-163(259)230-180(208)234-173(149)272)345-116(98)65-325-383(303,402)365-96-39-141(257-72-216-147-161(257)228-178(206)232-171(147)270)342-113(96)62-310-368(288,387)349-83-26-128(329-100(83)49-262)242-18-10-120(196)220-182(242)274)355-373(293,392)311-50-101-84(27-129(330-101)243-19-11-121(197)221-183(243)275)350-369(289,388)316-55-106-90(33-135(335-106)251-44-78(2)166(265)237-191(251)283)356-374(294,393)312-51-102-86(29-131(331-102)245-21-13-123(199)223-185(245)277)352-371(291,390)318-57-108-92(35-137(337-108)253-46-80(4)168(267)239-193(253)285)358-376(296,395)319-58-109-93(36-138(338-109)254-47-81(5)169(268)240-194(254)286)359-377(297,396)323-63-114-97(40-142(343-114)258-73-217-148-162(258)229-179(207)233-172(148)271)362-380(300,399)315-54-105-88(31-133(334-105)247-23-15-125(201)225-187(247)279)354-384(304,403)327-67-119-153(156(309-9)177(348-119)261-76-215-146-158(205)211-70-213-160(146)261)367-386(306,405)328-68-118-152(155(308-8)176(347-118)249-25-17-127(203)227-189(249)281)366-385(305,404)326-66-117-151(263)154(307-7)175(346-117)248-24-16-126(202)226-188(248)280/h10-25,43-48,69-76,83-119,128-144,151-156,175-177,262-263H,26-42,49-68H2,1-9H3,(H,288,387)(H,289,388)(H,290,389)(H,291,390)(H,292,391)(H,293,392)(H,294,393)(H,295,394)(H,296,395)(H,297,396)(H,298,397)(H,299,398)(H,300,399)(H,301,400)(H,302,401)(H,303,402)(H,304,403)(H,305,404)(H,306,405)(H2,196,220,274)(H2,197,221,275)(H2,198,222,276)(H2,199,223,277)(H2,200,224,278)(H2,201,225,279)(H2,202,226,280)(H2,203,227,281)(H2,204,210,212)(H2,205,211,213)(H,236,264,282)(H,237,265,283)(H,238,266,284)(H,239,267,285)(H,240,268,286)(H,241,269,287)(H3,206,228,232,270)(H3,207,229,233,271)(H3,208,230,234,272)(H3,209,231,235,273)
InChI Key UTNSIDJKCKLZLN-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
8843 cenersen
Synonyms Click here for help
Aezea® (proposed proprietary name) | EL625
Database Links Click here for help
GtoPdb PubChem SID 252166482
Search Google for chemical match using the InChIKey UTNSIDJKCKLZLN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UTNSIDJKCKLZLN
Search PubMed clinical trials cenersen
Search PubMed titles cenersen
Search PubMed titles/abstracts cenersen
UniChem Compound Search for chemical match using the InChIKey UTNSIDJKCKLZLN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UTNSIDJKCKLZLN-UHFFFAOYSA-N