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    Also known as: Kappaproct, Cobitolimod [inn], Cobitolimod [usan], Cobitolimod [who-dd], Dims 0150, Idx 0150
    Molecular Formula
    C185H233N73O106P18S6
    Molecular Weight
    5925  g/mol
    InChI Key
    IXYNFLOLUBKHQU-FZCWJHTDSA-N
    Cobitolimod
    Cobitolimod is under investigation in clinical trial NCT03178669 (The Efficacy of Cobitolimod in Patients With Moderate to Severe Active Ulcerative Colitis).
    1 2D Structure

    Cobitolimod

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-3-[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-[[[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(6-aminopurin-9-yl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-5-(6-aminopurin-9-yl)oxolan-3-yl] hydrogen phosphate
    2.1.2 InChI
    InChI=1S/C185H233N73O106P18S6/c1-71-34-245(182(276)236-161(71)261)123-21-81(100(334-123)44-314-371(292,293)353-83-23-125(247-36-73(3)163(263)238-184(247)278)336-102(83)46-316-373(296,297)357-87-28-133(255-67-215-143-157(255)226-173(197)232-167(143)267)341-106(87)50-320-374(298,299)354-84-24-127(249-61-209-137-147(191)201-57-205-151(137)249)338-103(84)47-317-366(282,283)349-80-20-122(244-14-9-117(190)223-181(244)275)333-99(80)43-313-375(300,301)358-88-26-129(251-63-211-139-149(193)203-59-207-153(139)251)342-108(88)52-323-379(306,385)362-90-30-130(252-64-212-140-150(194)204-60-208-154(140)252)343-109(90)53-325-381(308,387)363-92-32-135(257-69-217-145-159(257)228-175(199)234-169(145)269)344-110(92)54-324-378(305,384)359-76-16-131(328-94(76)38-259)253-65-213-141-155(253)224-171(195)230-165(141)265)351-369(288,289)312-42-98-79(19-121(332-98)243-13-8-116(189)222-180(243)274)350-368(286,287)319-49-105-86(27-132(340-105)254-66-214-142-156(254)225-172(196)231-166(142)266)356-372(294,295)315-45-101-82(22-124(335-101)246-35-72(2)162(262)237-183(246)277)352-370(290,291)311-41-97-77(17-119(331-97)241-11-6-114(187)220-178(241)272)347-365(280,281)310-40-96-78(18-120(330-96)242-12-7-115(188)221-179(242)273)348-367(284,285)318-48-104-85(25-128(339-104)250-62-210-138-148(192)202-58-206-152(138)250)355-376(302,303)321-51-107-89(29-126(337-107)248-37-74(4)164(264)239-185(248)279)360-380(307,386)326-56-112-93(33-136(346-112)258-70-218-146-160(258)229-176(200)235-170(146)270)364-382(309,388)327-55-111-91(31-134(345-111)256-68-216-144-158(256)227-174(198)233-168(144)268)361-377(304,383)322-39-95-75(260)15-118(329-95)240-10-5-113(186)219-177(240)271/h5-14,34-37,57-70,75-112,118-136,259-260H,15-33,38-56H2,1-4H3,(H,280,281)(H,282,283)(H,284,285)(H,286,287)(H,288,289)(H,290,291)(H,292,293)(H,294,295)(H,296,297)(H,298,299)(H,300,301)(H,302,303)(H,304,383)(H,305,384)(H,306,385)(H,307,386)(H,308,387)(H,309,388)(H2,186,219,271)(H2,187,220,272)(H2,188,221,273)(H2,189,222,274)(H2,190,223,275)(H2,191,201,205)(H2,192,202,206)(H2,193,203,207)(H2,194,204,208)(H,236,261,276)(H,237,262,277)(H,238,263,278)(H,239,264,279)(H3,195,224,230,265)(H3,196,225,231,266)(H3,197,226,232,267)(H3,198,227,233,268)(H3,199,228,234,269)(H3,200,229,235,270)/t75-,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+,109+,110+,111+,112+,118+,119+,120+,121+,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,132+,133+,134+,135+,136+,377?,378?,379?,380?,381?,382?/m0/s1
    2.1.3 InChI Key
    IXYNFLOLUBKHQU-FZCWJHTDSA-N
    2.1.4 Canonical SMILES
    CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OC3CC(OC3COP(=O)(O)OC4CC(OC4COP(=O)(O)OC5CC(OC5COP(=O)(O)OC6CC(OC6COP(=O)(O)OC7CC(OC7COP(=S)(O)OC8CC(OC8COP(=S)(O)OC9CC(OC9COP(=S)(O)OC1CC(OC1CO)N1C=NC2=C1N=C(NC2=O)N)N1C=NC2=C1N=C(NC2=O)N)N1C=NC2=C(N=CN=C21)N)N1C=NC2=C(N=CN=C21)N)N1C=CC(=NC1=O)N)N1C=NC2=C(N=CN=C21)N)N1C=NC2=C1N=C(NC2=O)N)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)OP(=O)(O)OCC1C(CC(O1)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=NC2=C1N=C(NC2=O)N)OP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)O
    2.1.5 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]4C[C@@H](O[C@@H]4COP(=O)(O)O[C@H]5C[C@@H](O[C@@H]5COP(=O)(O)O[C@H]6C[C@@H](O[C@@H]6COP(=O)(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]1C[C@@H](O[C@@H]1CO)N1C=NC2=C1N=C(NC2=O)N)N1C=NC2=C1N=C(NC2=O)N)N1C=NC2=C(N=CN=C21)N)N1C=NC2=C(N=CN=C21)N)N1C=CC(=NC1=O)N)N1C=NC2=C(N=CN=C21)N)N1C=NC2=C1N=C(NC2=O)N)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=CC(=NC1=O)N)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=CC(=NC1=O)N)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=CC(=NC1=O)N)OP(=O)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)OP(=O)(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=NC2=C1N=C(NC2=O)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=CC(=NC1=O)N)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. Kappaproct

    2. Cobitolimod [inn]

    3. Cobitolimod [usan]

    4. Cobitolimod [who-dd]

    5. Dims 0150

    6. Idx 0150

    7. Unii-328101264r

    8. Who 10066

    9. 328101264r

    10. Dna, D(g-sp-g-sp-a-sp-a-c-a-g-t-t-c-g-t-c-c-a-t-sp-g-sp-g-sp-c)

    11. 1226822-98-5

    2.3 Create Date
    2016-08-16
    3 Chemical and Physical Properties
    Molecular Weight 5925 g/mol
    Molecular Formula C185H233N73O106P18S6
    XLogP3-28.3
    Hydrogen Bond Donor Count45
    Hydrogen Bond Acceptor Count140
    Rotatable Bond Count110
    Exact Mass5922.8720822 g/mol
    Monoisotopic Mass5921.8687274 g/mol
    Topological Polar Surface Area2590 Ų
    Heavy Atom Count388
    Formal Charge0
    Complexity17500
    Isotope Atom Count0
    Defined Atom Stereocenter Count57
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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