bevasiranib   Click here for help

GtoPdb Ligand ID: 13629

Compound class: Nucleic acid
Comment: Bevasiranib (Cand5) is a small interfering RNA (siRNA; composed of two 21-nucleotide RNA molecules) that blocks translation and synthesis of vascular endothelial growth factor A (VEGFA) protein [1]. It was developed for anti-angiogenic actions for the treatment of age-related (wet) macular degeneration (AMD) [2]. Experimental evidence indicates a role for Toll-like receptor 3 (TLR3) activation in bevasiranib's mechanism of action in reducing wet AMD-associated choroidal neovascularization [3], since it is only effective in mice with intact TLR3 [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 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 218
Hydrogen bond donors 65
Rotatable bonds 122
Topological polar surface area 3253.78
Molecular weight 6610.08
XLogP -66.92
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 CC1=CN([C@H]2C[C@@H]([C@@H](COP(=O)(O)O[C@H]3C[C@H](N4C=C(C)C(=O)NC4=O)O[C@@H]3COP(=O)(O)O[C@@H]5[C@@H](COP(=O)(O)O[C@@H]6[C@@H](COP(=O)(O)O[C@@H]7[C@@H](COP(=O)(O)O[C@@H]8[C@@H](COP(=O)(O)O[C@@H]9[C@@H](COP(=O)(O)O[C@@H]%10[C@@H](COP(=O)(O)O[C@@H]%11[C@@H](COP(=O)(O)O[C@@H]%12[C@@H](COP(=O)(O)O[C@@H]%13[C@@H](COP(=O)(O)O[C@@H]%14[C@@H](COP(=O)(O)O[C@@H]%15[C@@H](COP(=O)(O)O[C@@H]%16[C@@H](COP(=O)(O)O[C@@H]%17[C@@H](COP(=O)(O)O[C@@H]%18[C@@H](COP(=O)(O)O[C@@H]%19[C@@H](COP(=O)(O)O[C@@H]%20[C@@H](COP(=O)(O)O[C@@H]%21[C@@H](COP(=O)(O)O[C@@H]%22[C@@H](COP(=O)(O)O[C@@H]%23[C@@H](CO)O[C@H]([C@@H]%23O)N%24C=NC%25=C%24N=CN=C%25N)O[C@H]([C@@H]%22O)N%26C=CC(=NC%26=O)N)O[C@H]([C@@H]%21O)N%27C=CC(=NC%27=O)N)O[C@H]([C@@H]%20O)N%28C=CC(=O)NC%28=O)O[C@H]([C@@H]%19O)N%29C=CC(=NC%29=O)N)O[C@H]([C@@H]%18O)N%30C=NC%31=C%30N=CN=C%31N)O[C@H]([C@@H]%17O)N%32C=CC(=NC%32=O)N)O[C@H]([C@@H]%16O)N%33C=CC(=NC%33=O)N)O[C@H]([C@@H]%15O)N%34C=NC%35=C%34N=CN=C%35N)O[C@H]([C@@H]%14O)N%36C=NC%37=C%36N=CN=C%37N)O[C@H]([C@@H]%13O)N%38C=NC%39=C%38N=C(N)NC%39=O)O[C@H]([C@@H]%12O)N%40C=NC%41=C%40N=C(N)NC%41=O)O[C@H]([C@@H]%11O)N%42C=CC(=NC%42=O)N)O[C@H]([C@@H]%10O)N%43C=CC(=NC%43=O)N)O[C@H]([C@@H]9O)N%44C=NC%45=C%44N=CN=C%45N)O[C@H]([C@@H]8O)N%46C=NC%47=C%46N=C(N)NC%47=O)O[C@H]([C@@H]7O)N%48C=CC(=NC%48=O)N)O[C@H]([C@@H]6O)N%49C=NC%50=C%49N=CN=C%50N)O[C@H]([C@@H]5O)N%51C=CC(=NC%51=O)N)O2)O)C(=O)NC1=O
Isomeric SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)O[C@H]3C[C@@H](O[C@@H]3COP(=O)(O)O[C@@H]4[C@H](O[C@H]([C@@H]4O)N5C=CC(=NC5=O)N)COP(=O)(O)O[C@@H]6[C@H](O[C@H]([C@@H]6O)N7C=NC8=C(N=CN=C87)N)COP(=O)(O)O[C@@H]9[C@H](O[C@H]([C@@H]9O)N%10C=CC(=NC%10=O)N)COP(=O)(O)O[C@@H]%11[C@H](O[C@H]([C@@H]%11O)N%12C=NC%13=C%12N=C(NC%13=O)N)COP(=O)(O)O[C@@H]%14[C@H](O[C@H]([C@@H]%14O)N%15C=NC%16=C(N=CN=C%16%15)N)COP(=O)(O)O[C@@H]%17[C@H](O[C@H]([C@@H]%17O)N%18C=CC(=NC%18=O)N)COP(=O)(O)O[C@@H]%19[C@H](O[C@H]([C@@H]%19O)N%20C=CC(=NC%20=O)N)COP(=O)(O)O[C@@H]%21[C@H](O[C@H]([C@@H]%21O)N%22C=NC%23=C%22N=C(NC%23=O)N)COP(=O)(O)O[C@@H]%24[C@H](O[C@H]([C@@H]%24O)N%25C=NC%26=C%25N=C(NC%26=O)N)COP(=O)(O)O[C@@H]%27[C@H](O[C@H]([C@@H]%27O)N%28C=NC%29=C(N=CN=C%29%28)N)COP(=O)(O)O[C@@H]%30[C@H](O[C@H]([C@@H]%30O)N%31C=NC%32=C(N=CN=C%32%31)N)COP(=O)(O)O[C@@H]%33[C@H](O[C@H]([C@@H]%33O)N%34C=CC(=NC%34=O)N)COP(=O)(O)O[C@@H]%35[C@H](O[C@H]([C@@H]%35O)N%36C=CC(=NC%36=O)N)COP(=O)(O)O[C@@H]%37[C@H](O[C@H]([C@@H]%37O)N%38C=NC%39=C(N=CN=C%39%38)N)COP(=O)(O)O[C@@H]%40[C@H](O[C@H]([C@@H]%40O)N%41C=CC(=NC%41=O)N)COP(=O)(O)O[C@@H]%42[C@H](O[C@H]([C@@H]%42O)N%43C=CC(=O)NC%43=O)COP(=O)(O)O[C@@H]%44[C@H](O[C@H]([C@@H]%44O)N%45C=CC(=NC%45=O)N)COP(=O)(O)O[C@@H]%46[C@H](O[C@H]([C@@H]%46O)N%47C=CC(=NC%47=O)N)COP(=O)(O)O[C@@H]%48[C@H](O[C@H]([C@@H]%48O)N%49C=NC%50=C(N=CN=C%50%49)N)CO)N%51C=C(C(=O)NC%51=O)C)O
InChI InChI=1S/C200H254N78O140P20/c1-63-25-268(199(316)256-162(63)301)98-23-65(280)68(378-98)28-358-419(318,319)399-66-24-99(269-26-64(2)163(302)257-200(269)317)379-69(66)29-359-420(320,321)401-129-71(382-167(110(129)283)258-13-3-88(201)240-189(258)306)31-366-431(342,343)411-139-80(391-178(120(139)293)271-55-232-101-148(211)220-49-226-154(101)271)40-371-430(340,341)409-137-78(389-175(118(137)291)266-21-11-96(209)248-197(266)314)38-369-434(348,349)416-144-85(396-183(125(144)298)276-60-237-106-159(276)250-186(216)253-164(106)303)45-375-436(352,353)414-142-83(394-181(123(142)296)274-58-235-104-151(214)223-52-229-157(104)274)43-373-429(338,339)407-135-74(385-173(116(135)289)264-19-9-94(207)246-195(264)312)34-363-424(328,329)404-133-77(388-171(114(133)287)262-17-7-92(205)244-193(262)310)37-368-433(346,347)417-145-87(398-184(126(145)299)277-61-238-107-160(277)251-187(217)254-165(107)304)47-377-438(356,357)418-146-86(397-185(127(146)300)278-62-239-108-161(278)252-188(218)255-166(108)305)46-376-437(354,355)415-143-84(395-182(124(143)297)275-59-236-105-152(215)224-53-230-158(105)275)44-374-435(350,351)413-141-82(393-180(122(141)295)273-57-234-103-150(213)222-51-228-156(103)273)42-372-428(336,337)406-134-73(384-172(115(134)288)263-18-8-93(206)245-194(263)311)33-362-423(326,327)403-132-76(387-170(113(132)286)261-16-6-91(204)243-192(261)309)36-367-432(344,345)412-140-81(392-179(121(140)294)272-56-233-102-149(212)221-50-227-155(102)272)41-370-427(334,335)408-136-75(386-174(117(136)290)265-20-10-95(208)247-196(265)313)35-364-426(332,333)410-138-79(390-176(119(138)292)267-22-12-97(281)249-198(267)315)39-365-425(330,331)405-131-72(383-169(112(131)285)260-15-5-90(203)242-191(260)308)32-361-422(324,325)402-130-70(381-168(111(130)284)259-14-4-89(202)241-190(259)307)30-360-421(322,323)400-128-67(27-279)380-177(109(128)282)270-54-231-100-147(210)219-48-225-153(100)270/h3-22,25-26,48-62,65-87,98-99,109-146,167-185,279-280,282-300H,23-24,27-47H2,1-2H3,(H,318,319)(H,320,321)(H,322,323)(H,324,325)(H,326,327)(H,328,329)(H,330,331)(H,332,333)(H,334,335)(H,336,337)(H,338,339)(H,340,341)(H,342,343)(H,344,345)(H,346,347)(H,348,349)(H,350,351)(H,352,353)(H,354,355)(H,356,357)(H2,201,240,306)(H2,202,241,307)(H2,203,242,308)(H2,204,243,309)(H2,205,244,310)(H2,206,245,311)(H2,207,246,312)(H2,208,247,313)(H2,209,248,314)(H2,210,219,225)(H2,211,220,226)(H2,212,221,227)(H2,213,222,228)(H2,214,223,229)(H2,215,224,230)(H,249,281,315)(H,256,301,316)(H,257,302,317)(H3,216,250,253,303)(H3,217,251,254,304)(H3,218,252,255,305)/t65-,66-,67+,68+,69+,70+,71+,72+,73+,74+,75+,76+,77+,78+,79+,80+,81+,82+,83+,84+,85+,86+,87+,98+,99+,109+,110+,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+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,178+,179+,180+,181+,182+,183+,184+,185+/m0/s1
InChI Key PRYZSLKPMFOUNL-MHIBGBBJSA-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 siRNA
Target VEGFA mRNA, Toll-like receptor 3
Database Links Click here for help
CAS Registry No. 959961-96-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL2110581
DrugBank Ligand DB06642
GtoPdb PubChem SID 504705448
PubChem CID 70695616
Search Google for chemical match using the InChIKey PRYZSLKPMFOUNL-MHIBGBBJSA-N
Search Google for chemicals with the same backbone PRYZSLKPMFOUNL
UniChem Compound Search for chemical match using the InChIKey PRYZSLKPMFOUNL-MHIBGBBJSA-N
UniChem Connectivity Search for chemical match using the InChIKey PRYZSLKPMFOUNL-MHIBGBBJSA-N