oblimersen   Click here for help

GtoPdb Ligand ID: 8269

Synonyms: DNA, D(P-thio)(T-C-T-C-C-C-A-G-C-G-T-G-C-G-C-C-A-T) | G3139 | Genasense®
Compound class: Synthetic organic
Comment: Oblimersen is an 18mer phosphorothioate DNA antisense oligonucleotide complementary to the first six codons of the open reading frame of Bcl-2 messenger RNA. The sequence is 5′-tct ccc agc gtg cgc cat-3′ [1].
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 153
Hydrogen bond donors 41
Rotatable bonds 104
Topological polar surface area 2708.79
Molecular weight 5684.64
XLogP -6.43
No. Lipinski's rules broken 4
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([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=CC(=NC7=O)N)O[C@@H]6COP(=S)(O)O[C@H]8C[C@H](N9C=CC(=NC9=O)N)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]%13C[C@H](N%14C=CC(=NC%14=O)N)O[C@@H]%13COP(=S)(O)O[C@H]%15C[C@H](N%16C=NC%17=C%16N=C(N)NC%17=O)O[C@@H]%15COP(=S)(O)O[C@H]%18C[C@H](N%19C=C(C)C(=O)NC%19=O)O[C@@H]%18COP(=S)(O)O[C@H]%20C[C@H](N%21C=NC%22=C%21N=C(N)NC%22=O)O[C@@H]%20COP(=S)(O)O[C@H]%23C[C@H](N%24C=CC(=NC%24=O)N)O[C@@H]%23COP(=S)(O)O[C@H]%25C[C@H](N%26C=NC%27=C%26N=C(N)NC%27=O)O[C@@H]%25COP(=S)(O)O[C@H]%28C[C@H](N%29C=NC%30=C%29N=CN=C%30N)O[C@@H]%28COP(=S)(O)O[C@H]%31C[C@H](N%32C=CC(=NC%32=O)N)O[C@@H]%31COP(=S)(O)O[C@H]%33C[C@H](N%34C=CC(=NC%34=O)N)O[C@@H]%33COP(=S)(O)O[C@H]%35C[C@H](N%36C=CC(=NC%36=O)N)O[C@@H]%35COP(=S)(O)O[C@H]%37C[C@H](N%38C=C(C)C(=O)NC%38=O)O[C@@H]%37COP(=S)(O)O[C@H]%39C[C@H](N%40C=CC(=NC%40=O)N)O[C@@H]%39COP(=S)(O)O[C@H]%41C[C@H](N%42C=C(C)C(=O)NC%42=O)O[C@@H]%41CO)O2)O)C(=O)NC1=O
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]5C[C@@H](O[C@@H]5COP(=S)(O)O[C@H]6C[C@@H](O[C@@H]6COP(=S)(O)O[C@H]7C[C@@H](O[C@@H]7COP(=S)(O)O[C@H]8C[C@@H](O[C@@H]8COP(=S)(O)O[C@H]9C[C@@H](O[C@@H]9COP(=S)(O)O[C@H]%10C[C@@H](O[C@@H]%10COP(=S)(O)O[C@H]%11C[C@@H](O[C@@H]%11COP(=S)(O)O[C@H]%12C[C@@H](O[C@@H]%12COP(=S)(O)O[C@H]%13C[C@@H](O[C@@H]%13COP(=S)(O)O[C@H]%14C[C@@H](O[C@@H]%14COP(=S)(O)O[C@H]%15C[C@@H](O[C@@H]%15COP(=S)(O)O[C@H]%16C[C@@H](O[C@@H]%16COP(=S)(O)O[C@H]%17C[C@@H](O[C@@H]%17COP(=S)(O)O[C@H]%18C[C@@H](O[C@@H]%18COP(=S)(O)O[C@H]%19C[C@@H](O[C@@H]%19CO)N%20C=C(C(=O)NC%20=O)C)N%21C=CC(=NC%21=O)N)N%22C=C(C(=O)NC%22=O)C)N%23C=CC(=NC%23=O)N)N%24C=CC(=NC%24=O)N)N%25C=CC(=NC%25=O)N)N%26C=NC%27=C(N=CN=C%27%26)N)N%28C=NC%29=C%28N=C(NC%29=O)N)N%30C=CC(=NC%30=O)N)N%31C=NC%32=C%31N=C(NC%32=O)N)N%33C=C(C(=O)NC%33=O)C)N%34C=NC%35=C%34N=C(NC%35=O)N)N%36C=CC(=NC%36=O)N)N%37C=NC%38=C%37N=C(NC%38=O)N)N%39C=CC(=NC%39=O)N)N%40C=CC(=NC%40=O)N)N%41C=NC%42=C(N=CN=C%42%41)N)O
InChI InChI=1S/C172H221N62O91P17S17/c1-69-39-225(169(253)213-149(69)237)117-21-73(236)92(292-117)44-274-326(257,343)320-85-33-129(229-63-191-135-141(181)187-61-189-143(135)229)303-103(85)55-285-332(263,349)314-79-27-122(221-17-9-113(177)201-165(221)249)295-95(79)47-278-330(261,347)312-78-26-121(220-16-8-112(176)200-164(220)248)298-98(78)50-280-338(269,355)322-87-35-131(231-65-193-137-145(231)205-157(183)209-153(137)241)305-105(87)57-287-334(265,351)316-81-29-124(223-19-11-115(179)203-167(223)251)299-99(81)51-281-339(270,356)323-88-36-132(232-66-194-138-146(232)206-158(184)210-154(138)242)307-107(88)59-289-337(268,354)319-84-32-128(228-42-72(4)152(240)216-172(228)256)302-102(84)54-284-341(272,358)325-90-38-134(234-68-196-140-148(234)208-160(186)212-156(140)244)306-106(90)58-288-335(266,352)317-82-30-125(224-20-12-116(180)204-168(224)252)300-100(82)52-282-340(271,357)324-89-37-133(233-67-195-139-147(233)207-159(185)211-155(139)243)308-108(89)60-290-342(273,359)321-86-34-130(230-64-192-136-142(182)188-62-190-144(136)230)304-104(86)56-286-333(264,350)315-80-28-123(222-18-10-114(178)202-166(222)250)296-96(80)48-277-328(259,345)310-76-24-119(218-14-6-110(174)198-162(218)246)294-94(76)46-276-329(260,346)311-77-25-120(219-15-7-111(175)199-163(219)247)297-97(77)49-279-336(267,353)318-83-31-127(227-41-71(3)151(239)215-171(227)255)301-101(83)53-283-331(262,348)313-75-23-118(217-13-5-109(173)197-161(217)245)293-93(75)45-275-327(258,344)309-74-22-126(291-91(74)43-235)226-40-70(2)150(238)214-170(226)254/h5-20,39-42,61-68,73-108,117-134,235-236H,21-38,43-60H2,1-4H3,(H,257,343)(H,258,344)(H,259,345)(H,260,346)(H,261,347)(H,262,348)(H,263,349)(H,264,350)(H,265,351)(H,266,352)(H,267,353)(H,268,354)(H,269,355)(H,270,356)(H,271,357)(H,272,358)(H,273,359)(H2,173,197,245)(H2,174,198,246)(H2,175,199,247)(H2,176,200,248)(H2,177,201,249)(H2,178,202,250)(H2,179,203,251)(H2,180,204,252)(H2,181,187,189)(H2,182,188,190)(H,213,237,253)(H,214,238,254)(H,215,239,255)(H,216,240,256)(H3,183,205,209,241)(H3,184,206,210,242)(H3,185,207,211,243)(H3,186,208,212,244)/t73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91+,92+,93+,94+,95+,96+,97+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,117+,118+,119+,120+,121+,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,132+,133+,134+,326?,327?,328?,329?,330?,331?,332?,333?,334?,335?,336?,337?,338?,339?,340?,341?,342?/m0/s1
InChI Key MIMNFCVQODTQDP-NDLVEFNKSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
8267 oblimersen
Synonyms Click here for help
DNA, D(P-thio)(T-C-T-C-C-C-A-G-C-G-T-G-C-G-C-C-A-T) | G3139 | Genasense®
Database Links Click here for help
CAS Registry No. 190977-41-4
ChEMBL Ligand CHEMBL2108324
GtoPdb PubChem SID 252166481
PubChem CID 118984458
Search Google for chemical match using the InChIKey MIMNFCVQODTQDP-NDLVEFNKSA-N
Search Google for chemicals with the same backbone MIMNFCVQODTQDP
Search PubMed clinical trials oblimersen
Search PubMed titles oblimersen
Search PubMed titles/abstracts oblimersen
UniChem Compound Search for chemical match using the InChIKey MIMNFCVQODTQDP-NDLVEFNKSA-N
UniChem Connectivity Search for chemical match using the InChIKey MIMNFCVQODTQDP-NDLVEFNKSA-N
Wikipedia Oblimersen