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    Chemistry

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    Also known as: Unii-6jon30sldt, 6jon30sldt, Isis-304801 sodium, Volanesorsen sodium [usan], Isis-304801 sodium salt, 1573402-50-2
    Molecular Formula
    C230H301N63Na19O125P19S19
    Molecular Weight
    7583  g/mol
    InChI Key
    SPPHBOGCCHYSLF-BXCMNDLWSA-A
    Volanesorsen
    1 2D Structure

    Volanesorsen

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    nonadecasodium;1-[(2R,4S,5R)-4-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-3-[[(2R,3R,4R,5R)-3-[[(2R,3R,4R,5R)-3-[[(2R,3R,4R,5R)-3-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-[[(2R,3R,4R,5R)-3-hydroxy-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-4-(2-methoxyethoxy)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxyoxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxyoxolan-2-yl]methoxy-oxidophosphinothioyl]oxyoxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-oxidophosphinothioyl]oxy-5-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-2-[[[(2R,3R,4R,5R)-2-[[[(2R,3R,4R,5R)-2-[[[(2R,3R,4R,5R)-5-(4-amino-5-methyl-2-oxopyrimidin-1-yl)-2-[[[(2R,3R,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-(2-methoxyethoxy)oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]-4-(2-methoxyethoxy)oxolan-3-yl]oxy-sulfidophosphoryl]oxymethyl]-4-(2-methoxyethoxy)oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]-4-(2-methoxyethoxy)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-oxidophosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C230H320N63O125P19S19.19Na/c1-98-55-274(217(308)254-178(98)231)142-45-112(400-419(322,438)361-70-124-113(46-143(381-124)275-56-99(2)179(232)255-218(275)309)401-423(326,442)367-76-130-119(52-149(387-130)288-92-248-152-183(236)242-89-245-186(152)288)407-427(330,446)369-78-132-121(54-151(389-132)290-94-252-156-190(290)260-215(240)263-202(156)306)408-425(328,444)365-72-125-114(47-144(382-125)276-57-100(3)180(233)256-219(276)310)406-428(331,447)372-81-134-160(171(354-38-28-344-18)206(393-134)283-64-107(10)196(300)269-226(283)317)412-432(335,451)375-84-137-163(173(356-40-30-346-20)208(395-137)285-66-109(12)198(302)271-228(285)319)415-435(338,454)377-86-139-165(175(358-42-32-348-22)210(397-139)287-68-111(14)200(304)273-230(287)321)416-436(339,455)379-87-140-166(176(359-43-33-349-23)212(398-140)292-96-250-154-185(238)244-91-247-188(154)292)417-430(333,449)371-80-133-158(295)168(351-35-25-341-15)204(391-133)282-63-106(9)195(299)268-225(282)316)123(380-142)71-362-421(324,440)403-117-50-147(279-61-104(7)193(297)266-223(279)314)386-128(117)75-366-426(329,445)409-120-53-150(289-93-251-155-189(289)259-214(239)262-201(155)305)388-131(120)77-368-424(327,443)405-118-51-148(280-62-105(8)194(298)267-224(280)315)385-127(118)74-364-422(325,441)404-116-49-146(278-60-103(6)192(296)265-222(278)313)384-126(116)73-363-420(323,439)402-115-48-145(277-58-101(4)181(234)257-220(277)311)383-129(115)79-370-429(332,448)411-162-136(394-207(172(162)355-39-29-345-19)284-65-108(11)197(301)270-227(284)318)83-374-434(337,453)414-164-138(396-209(174(164)357-41-31-347-21)286-67-110(13)199(303)272-229(286)320)85-376-433(336,452)413-161-135(392-205(170(161)353-37-27-343-17)281-59-102(5)182(235)258-221(281)312)82-378-437(340,456)418-167-141(399-213(177(167)360-44-34-350-24)293-97-253-157-191(293)261-216(241)264-203(157)307)88-373-431(334,450)410-159-122(69-294)390-211(169(159)352-36-26-342-16)291-95-249-153-184(237)243-90-246-187(153)291;;;;;;;;;;;;;;;;;;;/h55-68,89-97,112-151,158-177,204-213,294-295H,25-54,69-88H2,1-24H3,(H,322,438)(H,323,439)(H,324,440)(H,325,441)(H,326,442)(H,327,443)(H,328,444)(H,329,445)(H,330,446)(H,331,447)(H,332,448)(H,333,449)(H,334,450)(H,335,451)(H,336,452)(H,337,453)(H,338,454)(H,339,455)(H,340,456)(H2,231,254,308)(H2,232,255,309)(H2,233,256,310)(H2,234,257,311)(H2,235,258,312)(H2,236,242,245)(H2,237,243,246)(H2,238,244,247)(H,265,296,313)(H,266,297,314)(H,267,298,315)(H,268,299,316)(H,269,300,317)(H,270,301,318)(H,271,302,319)(H,272,303,320)(H,273,304,321)(H3,239,259,262,305)(H3,240,260,263,306)(H3,241,261,264,307);;;;;;;;;;;;;;;;;;;/q;19*+1/p-19/t112-,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+,147+,148+,149+,150+,151+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,204+,205+,206+,207+,208+,209+,210+,211+,212+,213+,419?,420?,421?,422?,423?,424?,425?,426?,427?,428?,429?,430?,431?,432?,433?,434?,435?,436?,437?;;;;;;;;;;;;;;;;;;;/m0.................../s1
    2.1.3 InChI Key
    SPPHBOGCCHYSLF-BXCMNDLWSA-A
    2.1.4 Canonical SMILES
    CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=S)([O-])OC3CC(OC3COP(=S)([O-])OC4CC(OC4COP(=S)([O-])OC5C(OC(C5OCCOC)N6C=C(C(=O)NC6=O)C)COP(=S)([O-])OC7C(OC(C7OCCOC)N8C=C(C(=O)NC8=O)C)COP(=S)([O-])OC9C(OC(C9OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)(OC1C(OC(C1OCCOC)N1C=NC2=C1N=C(NC2=O)N)COP(=S)([O-])OC1C(OC(C1OCCOC)N1C=NC2=C(N=CN=C21)N)CO)[S-])N1C=C(C(=NC1=O)N)C)N1C=C(C(=O)NC1=O)C)OP(=S)([O-])OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=S)([O-])OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=S)([O-])OCC1C(CC(O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OCC1C(CC(O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)OP(=S)([O-])OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=S)([O-])OCC1C(CC(O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OCC1C(C(C(O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OCC1C(C(C(O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OCC1C(C(C(O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OCC1C(C(C(O1)N1C=NC2=C(N=CN=C21)N)OCCOC)OP(=S)([O-])OCC1C(C(C(O1)N1C=C(C(=O)NC1=O)C)OCCOC)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
    2.1.5 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]5[C@H](O[C@H]([C@@H]5OCCOC)N6C=C(C(=O)NC6=O)C)COP(=S)([O-])O[C@@H]7[C@H](O[C@H]([C@@H]7OCCOC)N8C=C(C(=O)NC8=O)C)COP(=S)([O-])O[C@@H]9[C@H](O[C@H]([C@@H]9OCCOC)N1C=C(C(=NC1=O)N)C)COP(=O)(O[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=NC2=C1N=C(NC2=O)N)COP(=S)([O-])O[C@@H]1[C@H](O[C@H]([C@@H]1OCCOC)N1C=NC2=C(N=CN=C21)N)CO)[S-])N1C=C(C(=NC1=O)N)C)N1C=C(C(=O)NC1=O)C)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=O)NC1=O)C)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)OP(=S)([O-])OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=NC1=O)N)C)OP(=S)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=C(C(=O)NC1=O)C)OCCOC)OP(=S)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC2=C(N=CN=C21)N)OCCOC)OP(=S)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=C(C(=O)NC1=O)C)OCCOC)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. Unii-6jon30sldt

    2. 6jon30sldt

    3. Isis-304801 Sodium

    4. Volanesorsen Sodium [usan]

    5. Isis-304801 Sodium Salt

    6. 1573402-50-2

    2.3 Create Date
    2016-08-28
    3 Chemical and Physical Properties
    Molecular Weight 7583 g/mol
    Molecular Formula C230H301N63Na19O125P19S19
    Hydrogen Bond Donor Count25
    Hydrogen Bond Acceptor Count162
    Rotatable Bond Count156
    Exact Mass7579.6964806 g/mol
    Monoisotopic Mass7577.6897709 g/mol
    Topological Polar Surface Area2970 Ų
    Heavy Atom Count475
    Formal Charge0
    Complexity20400
    Isotope Atom Count0
    Defined Atom Stereocenter Count70
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count20
    4 Drug and Medication Information
    4.1 Drug Indication

    Waylivra is indicated as an adjunct to diet in adult patients with genetically confirmed familial chylomicronemia syndrome (FCS) and at high risk for pancreatitis, in whom response to diet and triglyceride lowering therapy has been inadequate.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    C10AX18

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