Vanillotoxin

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Vanillotoxin-1
Chemical structure of VaTx1
Names
Other names
Tau-theraphotoxin-Pc1a, VaTx1
Identifiers
3D model (JSmol)
ChemSpider
  • none
  • -1: InChI=1S/C173H245N45O50S8/c1-85(2)55-112-152(248)201-116(60-93-38-42-98(224)43-39-93)156(252)202-117(61-94-40-44-99(225)45-41-94)157(253)213-127(165(261)189-88(7)143(239)199-118(62-95-68-182-103-33-20-18-31-100(95)103)158(254)206-121(65-137(232)233)147(243)187-74-135(229)217-140(89(8)222)171(267)198-111(142(177)238)58-91-27-14-12-15-28-91)79-272-276-83-131-170(266)216-130-82-275-274-80-128(212-151(247)108(46-47-136(230)231)192-144(240)102(176)75-219)167(263)195-107(37-26-52-181-173(178)179)150(246)204-119(63-96-69-183-104-34-21-19-32-101(96)104)159(255)203-115(59-92-29-16-13-17-30-92)155(251)197-110(49-54-270-11)145(241)185-71-132(226)184-72-133(227)191-126(166(262)208-122(66-138(234)235)161(257)211-125(77-221)164(260)218-141(90(9)223)172(268)209-114(57-87(5)6)153(249)207-123(67-139(236)237)162(258)214-131)78-271-273-81-129(168(264)193-105(35-22-24-50-174)148(244)196-109(48-53-269-10)146(242)186-73-134(228)190-112)215-163(259)124(76-220)210-154(250)113(56-86(3)4)200-160(256)120(64-97-70-180-84-188-97)205-149(245)106(194-169(130)265)36-23-25-51-175/h12-21,27-34,38-45,68-70,84-90,102,105-131,140-141,182-183,219-225H,22-26,35-37,46-67,71-83,174-176H2,1-11H3,(H2,177,238)(H,180,188)(H,184,226)(H,185,241)(H,186,242)(H,187,243)(H,189,261)(H,190,228)(H,191,227)(H,192,240)(H,193,264)(H,194,265)(H,195,263)(H,196,244)(H,197,251)(H,198,267)(H,199,239)(H,200,256)(H,201,248)(H,202,252)(H,203,255)(H,204,246)(H,205,245)(H,206,254)(H,207,249)(H,208,262)(H,209,268)(H,210,250)(H,211,257)(H,212,247)(H,213,253)(H,214,258)(H,215,259)(H,216,266)(H,217,229)(H,218,260)(H,230,231)(H,232,233)(H,234,235)(H,236,237)(H4,178,179,181)/t88-,89+,90+,102-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,140-,141-/m0/s1
    Key: RXRVLNDKXAOPHX-ZWNIUGCHSA-N
  • -2: InChI=1S/C164H235N45O49S7/c1-79(2)49-103-138(233)176-65-124(217)175-66-125(218)183-117-72-260-263-75-120-159(254)185-97(35-22-24-45-165)140(235)188-101(44-48-259-11)137(232)177-67-126(219)182-104(50-80(3)4)144(239)198-112(59-130(225)226)151(246)194-107(54-88-38-40-92(215)41-39-88)147(242)204-118(156(251)181-83(8)136(231)190-108(55-89-62-173-95-33-20-18-31-93(89)95)148(243)197-111(58-129(223)224)139(234)178-68-127(220)208-132(84(9)213)162(257)189-102(134(168)229)52-86-27-14-12-15-28-86)73-261-265-77-122(205-152(247)113(60-131(227)228)199-153(248)115(70-211)202-163(258)133(85(10)214)209-155(250)116(71-212)200-142(237)98(184-157(117)252)36-23-25-46-166)161(256)207-121(160(255)187-100(42-43-128(221)222)143(238)196-110(57-91-64-171-78-179-91)150(245)192-105(51-81(5)6)145(240)201-114(69-210)154(249)206-120)76-264-262-74-119(203-135(230)82(7)180-123(216)61-167)158(253)186-99(37-26-47-172-164(169)170)141(236)195-109(56-90-63-174-96-34-21-19-32-94(90)96)149(244)193-106(146(241)191-103)53-87-29-16-13-17-30-87/h12-21,27-34,38-41,62-64,78-85,97-122,132-133,173-174,210-215H,22-26,35-37,42-61,65-77,165-167H2,1-11H3,(H2,168,229)(H,171,179)(H,175,217)(H,176,233)(H,177,232)(H,178,234)(H,180,216)(H,181,251)(H,182,219)(H,183,218)(H,184,252)(H,185,254)(H,186,253)(H,187,255)(H,188,235)(H,189,257)(H,190,231)(H,191,241)(H,192,245)(H,193,244)(H,194,246)(H,195,236)(H,196,238)(H,197,243)(H,198,239)(H,199,248)(H,200,237)(H,201,240)(H,202,258)(H,203,230)(H,204,242)(H,205,247)(H,206,249)(H,207,256)(H,208,220)(H,209,250)(H,221,222)(H,223,224)(H,225,226)(H,227,228)(H4,169,170,172)/t82-,83-,84+,85+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,132-,133-/m0/s1
    Key: UPLRCWJFIYOZKF-QTQHHIRPSA-N
  • -3: InChI=1S/C184H242N48O54S6/c1-89(2)55-120-155(258)199-75-143(239)198-76-144(240)204-136-81-287-289-84-139-182(285)223-130(66-100-74-192-88-202-100)173(276)226-135(80-235)177(280)217-124(60-94-35-39-102(237)40-36-94)167(270)221-125(61-95-69-194-108-27-14-10-23-103(95)108)168(271)209-116(44-50-148(246)247)159(262)219-128(64-98-72-197-111-30-17-13-26-106(98)111)171(274)231-140(181(284)215-122(57-91(5)6)165(268)220-127(63-97-71-196-110-29-16-12-25-105(97)110)170(273)224-131(67-151(252)253)156(259)200-77-145(241)203-133(78-233)175(278)212-119(153(188)256)58-92-21-8-7-9-22-92)85-291-292-86-141(230-163(266)118(46-52-150(250)251)210-176(279)134(79-234)227-174(277)132(68-152(254)255)225-161(264)115(43-49-147(244)245)207-157(260)112(205-178(136)281)31-18-19-53-185)183(286)232-138(180(283)211-117(45-51-149(248)249)160(263)222-129(65-99-73-191-87-201-99)172(275)214-121(56-90(3)4)164(267)208-114(162(265)229-139)42-47-142(187)238)83-290-288-82-137(228-154(257)107(186)41-48-146(242)243)179(282)206-113(32-20-54-193-184(189)190)158(261)218-126(62-96-70-195-109-28-15-11-24-104(96)109)169(272)216-123(166(269)213-120)59-93-33-37-101(236)38-34-93/h7-17,21-30,33-40,69-74,87-91,107,112-141,194-197,233-237H,18-20,31-32,41-68,75-86,185-186H2,1-6H3,(H2,187,238)(H2,188,256)(H,191,201)(H,192,202)(H,198,239)(H,199,258)(H,200,259)(H,203,241)(H,204,240)(H,205,281)(H,206,282)(H,207,260)(H,208,267)(H,209,271)(H,210,279)(H,211,283)(H,212,278)(H,213,269)(H,214,275)(H,215,284)(H,216,272)(H,217,280)(H,218,261)(H,219,262)(H,220,268)(H,221,270)(H,222,263)(H,223,285)(H,224,273)(H,225,264)(H,226,276)(H,227,277)(H,228,257)(H,229,265)(H,230,266)(H,231,274)(H,232,286)(H,242,243)(H,244,245)(H,246,247)(H,248,249)(H,250,251)(H,252,253)(H,254,255)(H4,189,190,193)/t107-,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-/m0/s1
    Key: KUMJPNKYKZAIIW-OSPWSWGCSA-N
  • -1: N[C@@]([H])(CO)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N[C@@]([H])(CCSC)C(=O)NCC(=O)NCC(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CC1=CN=C-N1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CCSC)C(=O)NCC(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(C)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CC(=O)O)C(=O)NCC(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N
  • -2: NCC(=O)N[C@@]([H])(C)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N[C@@]([H])(CC(C)C)C(=O)NCC(=O)NCC(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CC1=CN=C-N1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CCSC)C(=O)NCC(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(C)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CC(=O)O)C(=O)NCC(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N
  • -3: N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CC(C)C)C(=O)NCC(=O)NCC(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(CS3)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CC1=CN=C-N1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CCC(=O)N)C(=O)N[C@@]([H])(CS4)C(=O)N[C@@]([H])(CC1=CN=C-N1)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CS5)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CC(=O)O)C(=O)NCC(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N
Properties
Molar mass 4008.5 g/mol[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vanillotoxins (VaTxs, subtypes VaTx1, VaTx2, and VaTx3) are neurotoxins found in the venom of the tarantula Psalmopoeus cambridgei. They act as agonists for the transient receptor potential cation channel subfamily V member 1 (TRPV1), activating the pain sensory system. VaTx1 and 2 also act as antagonists for the Kv2-type voltage-gated potassium channel (Kv2), inducing paralytic behavior in small animals.[1]

P. cambridgei, a tarantula from Trinidad, uses its venom to paralyze its prey. Amongst other compounds, this venom contains all three subtypes of VaTxs: VaTx1, VaTx2, and VaTx3.[1] The name of the toxin was derived from the vanilloid receptor TRPV1, to which the VaTxs bind.

Chemistry

Vanillotoxins have close homology to other inhibitor cystine knot (ICK) toxins.[1] ICK toxins are best known as blockers of cation channels.[2] The exact structure of the VaTxs has not yet been deduced, although some preliminary models have been proposed. VaTxs are 53-82% identical in amino acid sequence.[3] VaTx1 and VaTx2 have an almost identical structure, while VaTx3 shows some diversity in its extruding protein loop.

Targets

Mode of action

References

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