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    Chemistry

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    Also known as: Prexigebersen [inn], Prexigebersen [usan:inn], Unii-8w1o4y961b, 8w1o4y961b, Bp-100-1.01/l-grb2, Dna, d(a-t-a-t-t-t-g-g-c-g-a-t-g-g-c-t-t-c)
    Molecular Formula
    C177H224N63O110P17
    Molecular Weight
    5521  g/mol
    InChI Key
    QAOIWVZTHIWLSW-UHFFFAOYSA-N
    Prexigebersen
    Prexigebersen is a liposomal formulation containing the antisense oligodeoxynucleotide (ODN) growth factor receptor-bound protein 2 (Grb2), with potential antineoplastic activity. Upon administration, liposome-incorporated Grb2 antisense oligodeoxynucleotide binds directly to and blocks Grb2 mRNA, thereby preventing Grb2 protein synthesis, leading to inhibition of cell proliferation of cancer cells overexpressing Grb2. Grb2, an adaptor protein involved in growth signaling pathways, is upregulated in certain tumor cells.
    1 2D Structure

    Prexigebersen

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(4-amino-2-oxopyrimidin-1-yl)-3-[[3-[[3-[[5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-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]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]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]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-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]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-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate
    2.1.2 InChI
    InChI=1S/C177H224N63O110P17/c1-68-32-226(171(258)216-151(68)243)117-18-79(337-351(265,266)299-40-94-75(242)14-114(317-94)223-11-8-111(178)203-168(223)255)98(321-117)44-304-355(273,274)338-81-20-119(228-34-70(3)153(245)218-173(228)260)322-99(81)45-303-353(269,270)335-77-16-115(224-12-9-112(179)204-169(224)256)318-95(77)41-301-361(285,286)346-88-27-127(236-63-198-135-146(236)206-163(184)211-158(135)250)332-109(88)55-314-367(297,298)350-92-31-131(240-67-202-139-150(240)210-167(188)215-162(139)254)331-108(92)54-313-360(283,284)343-85-24-123(232-38-74(7)157(249)222-177(232)264)326-103(85)49-308-364(291,292)345-87-26-126(235-62-197-134-142(183)191-59-194-145(134)235)328-105(87)51-310-365(293,294)348-90-29-129(238-65-200-137-148(238)208-165(186)213-160(137)252)329-106(90)52-311-354(271,272)336-78-17-116(225-13-10-113(180)205-170(225)257)319-96(78)42-302-362(287,288)347-89-28-128(237-64-199-136-147(237)207-164(185)212-159(136)251)333-110(89)56-315-366(295,296)349-91-30-130(239-66-201-138-149(239)209-166(187)214-161(138)253)330-107(91)53-312-359(281,282)342-84-23-122(231-37-73(6)156(248)221-176(231)263)324-101(84)47-306-356(275,276)339-82-21-120(229-35-71(4)154(246)219-174(229)261)323-100(82)46-305-357(277,278)340-83-22-121(230-36-72(5)155(247)220-175(230)262)325-102(83)48-307-363(289,290)344-86-25-125(234-61-196-133-141(182)190-58-193-144(133)234)327-104(86)50-309-358(279,280)341-80-19-118(227-33-69(2)152(244)217-172(227)259)320-97(80)43-300-352(267,268)334-76-15-124(316-93(76)39-241)233-60-195-132-140(181)189-57-192-143(132)233/h8-13,32-38,57-67,75-110,114-131,241-242H,14-31,39-56H2,1-7H3,(H,265,266)(H,267,268)(H,269,270)(H,271,272)(H,273,274)(H,275,276)(H,277,278)(H,279,280)(H,281,282)(H,283,284)(H,285,286)(H,287,288)(H,289,290)(H,291,292)(H,293,294)(H,295,296)(H,297,298)(H2,178,203,255)(H2,179,204,256)(H2,180,205,257)(H2,181,189,192)(H2,182,190,193)(H2,183,191,194)(H,216,243,258)(H,217,244,259)(H,218,245,260)(H,219,246,261)(H,220,247,262)(H,221,248,263)(H,222,249,264)(H3,184,206,211,250)(H3,185,207,212,251)(H3,186,208,213,252)(H3,187,209,214,253)(H3,188,210,215,254)
    2.1.3 InChI Key
    QAOIWVZTHIWLSW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CN(C(=O)NC1=O)C2CC(C(O2)COP(=O)(O)OC3CC(OC3CO)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)OCC6C(CC(O6)N7C=NC8=C(N=CN=C87)N)OP(=O)(O)OCC9C(CC(O9)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)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=NC2=C(N=CN=C21)N)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)OP(=O)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. Prexigebersen [inn]

    2. Prexigebersen [usan:inn]

    3. Unii-8w1o4y961b

    4. 8w1o4y961b

    5. Bp-100-1.01/l-grb2

    6. Dna, D(a-t-a-t-t-t-g-g-c-g-a-t-g-g-c-t-t-c)

    7. 202484-91-1

    2.3 Create Date
    2017-01-03
    3 Chemical and Physical Properties
    Molecular Weight 5521 g/mol
    Molecular Formula C177H224N63O110P17
    XLogP3-34.9
    Hydrogen Bond Donor Count42
    Hydrogen Bond Acceptor Count132
    Rotatable Bond Count104
    Exact Mass5518.9443863 g/mol
    Monoisotopic Mass5517.9410315 g/mol
    Topological Polar Surface Area2310 Ų
    Heavy Atom Count367
    Formal Charge0
    Complexity16500
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count54
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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