Details of the Drug

General Information of Drug (ID: DMIEB8Y)

Drug Name

Bevasiranib

Indication

Disease Entry	ICD 11	Status	REF
Exudative age-related macular degeneration	9B78.3Z	Discontinued in Phase 3	[1]
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Therapeutic Class

siRNA

Drug Type

siRNA drug

Sequence

>RNA, (A-C-C-U-C-A-C-C-A-A-G-G-C-C-A-G-C-A-C-DT-DT), COMPLEX WITH RNA (G-U-G-C-U-G-G-C-C-U-U-G-G-U-G-A-G-G-U-DT-DT) (1
1)

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

6610

Logarithm of the Partition Coefficient (xlogp)

-61.1

Rotatable Bond Count (rotbonds)

122

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

170

Chemical Identifiers

Formula: C200H254N78O140P20
IUPAC Name: [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R,5R)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-[[(2R,3S,4R,5R)-3-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-3-[hydroxy-[[(2R,3S,5R)-3-[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxyoxolan-2-yl]methyl hydrogen phosphate
Canonical 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)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC2=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C(N=CN=C21)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC2=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C1N=C(NC2=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C(N=CN=C21)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C(N=CN=C21)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C(N=CN=C21)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=CC(=NC1=O)N)COP(=O)(O)O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C=NC2=C(N=CN=C21)N)CO)N1C=C(C(=O)NC1=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
InChIKey: PRYZSLKPMFOUNL-MHIBGBBJSA-N

Cross-matching ID

PubChem CID: 70695616
DrugBank ID: DB06642
TTD ID: D0YG4I

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Vascular endothelial growth factor A (VEGFA)	TTOHSBA	VEGFA_HUMAN	Modulator	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Exudative age-related macular degeneration

ICD Disease Classification

9B78.3Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Vascular endothelial growth factor A (VEGFA)	DTT	VEGFA	3.61E-01	0.15	0.47

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	2011 Pipeline of Acuity Pharmaceuticals.
2	Bevasiranib for the Treatment of Wet, Age-Related Macular Degeneration