Term: | desirudin |
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Accession: | CHEBI:140427
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Definition: | A heterodetic cyclic peptide composed of 65 amino acids joined in sequence and cyclised by three disulfide bridges between cysteine residues 6-14, 16-28 and 22-39. It is a highly specific inhibitor of thrombin and used as an anticoagulant in patients to prevent venous thromboembolism. Its amino acid sequence differs from natural hirudin by lack of sulfate group on Tyr-63. |
Synonyms: | exact_synonym: | L-valyl-L-valyl-L-tyrosyl-L-threonyl-L-alpha-aspartyl-L-cysteinyl-L-threonyl-L-alpha-glutamyl-L-seryl-glycyl-L-glutaminyl-L-asparagyl-L-leucyl-L-cysteinyl-L-leucyl-L-cysteinyl-L-alpha-glutamyl-glycyl-L-seryl-L-asparagyl-L-valyl-L-cysteinyl-glycyl-L-glutaminyl-glycyl-L-asparagyl-L-lysyl-L-cysteinyl-L-isoleucyl-L-leucyl-glycyl-L-seryl-L-alpha-aspartyl-glycyl-L-alpha-glutamyl-L-lysyl-L-asparagyl-L-glutaminyl-L-cysteinyl-L-valyl-L-threonyl-glycyl-L-alpha-glutamyl-glycyl-L-threonyl-L-prolyl-L-lysyl-L-prolyl-L-glutaminyl-L-seryl-L-histidyl-L-asparagyl-L-alpha-aspartyl-glycyl-L-alpha-aspartyl-L-phenylalanyl-L-alpha-glutamyl-L-alpha-glutamyl-L-isoleucyl-L-prolyl-L-alpha-glutamyl-L-alpha-glutamyl-L-tyrosyl-L-leucyl-L-glutamine (6->14),(16->28),(22->39)-tris(disulfide) |
| related_synonym: | 63-desulfohirudin (Hirudo medicinalis isoform HV1); CGP-39393; Formula=C287H440N80O110S6; IK-HIR02; InChI=1S/C287H440N80O110S6/c1-25-133(19)226-281(470)345-161(87-125(3)4)235(424)306-111-208(395)320-180(116-370)266(455)344-175(101-219(415)416)237(426)307-105-202(389)316-151(62-75-212(401)402)242(431)321-145(41-30-33-81-288)240(429)339-170(96-197(297)384)258(447)326-152(57-70-193(293)380)249(438)351-185(121-481-478-118-182-239(428)310-107-201(388)313-147(55-68-191(291)378)232(421)303-108-205(392)317-169(95-196(296)383)257(446)322-146(42-31-34-82-289)241(430)350-186(271(460)360-226)122-482-479-119-183(268(457)323-149(61-74-211(399)400)234(423)304-110-207(394)319-179(115-369)265(454)342-173(99-200(300)387)264(453)357-223(130(13)14)279(468)355-182)352-253(442)164(90-128(9)10)335-269(458)184-120-480-483-123-187(354-262(451)177(103-221(419)420)347-283(472)230(137(23)374)362-263(452)167(93-141-49-53-144(377)54-50-141)346-278(467)224(131(15)16)359-276(465)222(301)129(11)12)272(461)363-229(136(22)373)282(471)330-157(66-79-216(409)410)248(437)348-178(114-368)238(427)309-106-203(390)315-150(56-69-192(292)379)243(432)340-171(97-198(298)385)259(448)334-163(89-127(7)8)252(441)353-184)270(459)358-225(132(17)18)280(469)364-228(135(21)372)277(466)311-112-204(391)314-148(60-73-210(397)398)233(422)305-113-209(396)356-231(138(24)375)286(475)367-86-38-46-190(367)275(464)331-159(43-32-35-83-290)284(473)365-84-36-44-188(365)273(462)328-153(58-71-194(294)381)247(436)349-181(117-371)267(456)338-168(94-142-104-302-124-312-142)256(445)341-172(98-199(299)386)260(449)343-174(100-218(413)414)236(425)308-109-206(393)318-176(102-220(417)418)261(450)337-165(91-139-39-28-27-29-40-139)254(443)327-154(63-76-213(403)404)244(433)325-158(67-80-217(411)412)250(439)361-227(134(20)26-2)285(474)366-85-37-45-189(366)274(463)329-156(65-78-215(407)408)245(434)324-155(64-77-214(405)406)246(435)336-166(92-140-47-51-143(376)52-48-140)255(444)333-162(88-126(5)6)251(440)332-160(287(476)477)59-72-195(295)382/h27-29,39-40,47-54,104,124-138,145-190,222-231,368-377H,25-26,30-38,41-46,55-103,105-123,288-290,301H2,1-24H3,(H2,291,378)(H2,292,379)(H2,293,380)(H2,294,381)(H2,295,382)(H2,296,383)(H2,297,384)(H2,298,385)(H2,299,386)(H2,300,387)(H,302,312)(H,303,421)(H,304,423)(H,305,422)(H,306,424)(H,307,426)(H,308,425)(H,309,427)(H,310,428)(H,311,466)(H,313,388)(H,314,391)(H,315,390)(H,316,389)(H,317,392)(H,318,393)(H,319,394)(H,320,395)(H,321,431)(H,322,446)(H,323,457)(H,324,434)(H,325,433)(H,326,447)(H,327,443)(H,328,462)(H,329,463)(H,330,471)(H,331,464)(H,332,440)(H,333,444)(H,334,448)(H,335,458)(H,336,435)(H,337,450)(H,338,456)(H,339,429)(H,340,432)(H,341,445)(H,342,454)(H,343,449)(H,344,455)(H,345,470)(H,346,467)(H,347,472)(H,348,437)(H,349,436)(H,350,430)(H,351,438)(H,352,442)(H,353,441)(H,354,451)(H,355,468)(H,356,396)(H,357,453)(H,358,459)(H,359,465)(H,360,460)(H,361,439)(H,362,452)(H,363,461)(H,364,469)(H,397,398)(H,399,400)(H,401,402)(H,403,404)(H,405,406)(H,407,408)(H,409,410)(H,411,412)(H,413,414)(H,415,416)(H,417,418)(H,419,420)(H,476,477)/t133-,134-,135+,136+,137+,138+,145-,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,183-,184-,185-,186-,187-,188-,189-,190-,222-,223-,224-,225-,226-,227-,228-,229-,230-,231-/m0/s1; InChIKey=XYWBJDRHGNULKG-OUMQNGNKSA-N; Iprivask; Revasc; SMILES=CC[C@H](C)[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CSSC[C@@H]2NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)CNC2=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N1)C(C)C)C(C)C)[C@@H](C)O)[C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O; VVYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ; VVYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ (disulfide bridge: 6->14; 16->28; 22->39); desirudin recombinant; desirudina; desirudine; desirudinum; desulfatohirudin; desulphatohirudin; desulphatohirudin HV1 |
| xref: | CAS:120993-53-5; Chemspider:16743713; Drug_Central:2990; KEGG:D03692; PMID:10598155; PMID:12090145; PMID:1710836; PMID:19915180; PMID:2057916; PMID:2096492; PMID:21045759; PMID:21646070; PMID:21932952; PMID:22672318; PMID:23344102; PMID:2363121; PMID:2688102; PMID:2749592; PMID:33774764; PMID:7504125; PMID:7589048; PMID:7719527; PMID:7831657; PMID:7979736; PMID:8329573; PMID:8409044; PMID:8596376; PMID:8684139; Patent:NZ248558 |
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