Prexigebersen

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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 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 Formula	C₁₇₇H₂₂₄N₆₃O₁₁₀P₁₇
Molecular Weight	5521 g/mol
XLogP3	-34.9
Hydrogen Bond Donor Count	42
Hydrogen Bond Acceptor Count	132
Rotatable Bond Count	104
Exact Mass	5518.9443863 g/mol
Monoisotopic Mass	5517.9410315 g/mol
Topological Polar Surface Area	2310 Å²
Heavy Atom Count	367
Formal Charge	0
Complexity	16500
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	54
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1