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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:lepirudin
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Accession:CHEBI:142437 term browser browse the term
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 with heparin-induced thrombocytopenia.
Synonyms:exact_synonym: L-leucyl-L-threonyl-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: 1-Leu-2-Thr-63-desulfohirudin;   Formula=C287H440N80O111S6;   H-Leu-Thr-Tyr-Thr-Asp-Cys(1)-Thr-Glu-Ser-Gly-Gln-Asn-Leu-Cys(1)-Leu-Cys(2)-Glu-Gly-Ser-Asn-Val-Cys(3)-Gly-Gln-Gly-Asn-Lys-Cys(2)-Ile-Leu-Gly-Ser-Asp-Gly-Glu-Lys-Asn-Gln-Cys(3)-Val-Thr-Gly-Glu-Gly-Thr-Pro-Lys-Pro-Gln-Ser-His-Asn-Asp-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-Gln-OH;   Hbw-023;   InChI=1S/C287H440N80O111S6/c1-24-132(17)225-280(470)345-162(87-126(5)6)236(426)306-111-209(396)320-181(116-370)267(457)344-176(101-220(416)417)238(428)307-105-203(390)316-152(61-74-213(402)403)243(433)321-146(40-29-32-80-288)241(431)339-171(96-198(298)385)259(449)326-153(56-69-194(294)381)250(440)351-186(121-482-479-118-183-240(430)310-107-202(389)313-148(54-67-192(292)379)233(423)303-108-206(393)317-170(95-197(297)384)258(448)322-147(41-30-33-81-289)242(432)350-187(272(462)359-225)122-483-480-119-184(269(459)323-150(60-73-212(400)401)235(425)304-110-208(395)319-180(115-369)266(456)342-174(99-201(301)388)265(455)357-223(130(13)14)278(468)355-183)352-254(444)165(90-129(11)12)335-270(460)185-120-481-484-123-188(354-263(453)178(103-222(420)421)347-283(473)230(137(22)375)362-264(454)168(93-141-48-52-144(378)53-49-141)346-282(472)228(135(20)373)361-232(422)145(291)86-125(3)4)273(463)363-229(136(21)374)281(471)330-158(65-78-217(410)411)249(439)348-179(114-368)239(429)309-106-204(391)315-151(55-68-193(293)380)244(434)340-172(97-199(299)386)260(450)334-164(89-128(9)10)253(443)353-185)271(461)358-224(131(15)16)279(469)364-227(134(19)372)277(467)311-112-205(392)314-149(59-72-211(398)399)234(424)305-113-210(397)356-231(138(23)376)286(476)367-85-37-45-191(367)276(466)331-160(42-31-34-82-290)284(474)365-83-35-43-189(365)274(464)328-154(57-70-195(295)382)248(438)349-182(117-371)268(458)338-169(94-142-104-302-124-312-142)257(447)341-173(98-200(300)387)261(451)343-175(100-219(414)415)237(427)308-109-207(394)318-177(102-221(418)419)262(452)337-166(91-139-38-27-26-28-39-139)255(445)327-155(62-75-214(404)405)245(435)325-159(66-79-218(412)413)251(441)360-226(133(18)25-2)285(475)366-84-36-44-190(366)275(465)329-157(64-77-216(408)409)246(436)324-156(63-76-215(406)407)247(437)336-167(92-140-46-50-143(377)51-47-140)256(446)333-163(88-127(7)8)252(442)332-161(287(477)478)58-71-196(296)383/h26-28,38-39,46-53,104,124-138,145-191,223-231,368-378H,24-25,29-37,40-45,54-103,105-123,288-291H2,1-23H3,(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)(H2,301,388)(H,302,312)(H,303,423)(H,304,425)(H,305,424)(H,306,426)(H,307,428)(H,308,427)(H,309,429)(H,310,430)(H,311,467)(H,313,389)(H,314,392)(H,315,391)(H,316,390)(H,317,393)(H,318,394)(H,319,395)(H,320,396)(H,321,433)(H,322,448)(H,323,459)(H,324,436)(H,325,435)(H,326,449)(H,327,445)(H,328,464)(H,329,465)(H,330,471)(H,331,466)(H,332,442)(H,333,446)(H,334,450)(H,335,460)(H,336,437)(H,337,452)(H,338,458)(H,339,431)(H,340,434)(H,341,447)(H,342,456)(H,343,451)(H,344,457)(H,345,470)(H,346,472)(H,347,473)(H,348,439)(H,349,438)(H,350,432)(H,351,440)(H,352,444)(H,353,443)(H,354,453)(H,355,468)(H,356,397)(H,357,455)(H,358,461)(H,359,462)(H,360,441)(H,361,422)(H,362,454)(H,363,463)(H,364,469)(H,398,399)(H,400,401)(H,402,403)(H,404,405)(H,406,407)(H,408,409)(H,410,411)(H,412,413)(H,414,415)(H,416,417)(H,418,419)(H,420,421)(H,477,478)/t132-,133-,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-,191-,223-,224-,225-,226-,227-,228-,229-,230-,231-/m0/s1;   InChIKey=FIBJDTSHOUXTKV-BRHMIFOHSA-N;   LTYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ;   LTYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ (disulfide bridge: 6->14; 16->28; 22->39);   NH2-LTYTDCTESGQNLCLCEGSNVCGQGNKCILGSDGEKNQCVTGEGTPKPQSHNDGDFEEIPEEYLQ-OH;   Refludan;   SMILES=C(N1[C@H](C(N[C@H](C(N2[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CC(=O)O)C(NCC(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N3[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(=O)O)CCC(=O)N)=O)CC(C)C)=O)CC4=CC=C(O)C=C4)=O)CCC(=O)O)=O)CCC(=O)O)=O)CCC3)=O)[C@H](CC)C)=O)CCC(=O)O)=O)CCC(=O)O)=O)CC=5C=CC=CC5)=O)CC(=O)O)=O)=O)=O)CC(=O)N)=O)CC=6N=CNC6)=O)CO)=O)CCC(=O)N)=O)CCC2)=O)CCCCN)=O)CCC1)([C@@H](NC(=O)CNC([C@@H](NC(=O)CNC([C@@H](NC([C@@H](NC([C@H]7NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@H]8NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@H]9NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CSSC9)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](CC(C)C)N)=O)[C@H](O)C)=O)CC%10=CC=C(C=C%10)O)=O)[C@H](O)C)=O)CC(=O)O)=O)=O)[C@H](O)C)=O)CCC(=O)O)=O)CO)=O)=O)CCC(=O)N)=O)CC(=O)N)=O)CC(C)C)=O)=O)CC(C)C)=O)CSSC8)=O)CCC(=O)O)=O)=O)CO)=O)CC(=O)N)=O)C(C)C)=O)CSSC7)=O)=O)CCC(=O)N)=O)=O)CC(=O)N)=O)CCCCN)=O)=O)[C@H](CC)C)=O)CC(C)C)=O)=O)CO)=O)CC(=O)O)=O)=O)CCC(=O)O)=O)CCCCN)=O)CC(=O)N)=O)CCC(=O)N)=O)=O)C(C)C)=O)[C@H](O)C)=O)CCC(=O)O)=O)[C@H](O)C)=O;   [Leu1, Thr2]-63-desulfohirudin;   hirudin variant-1;   lepirudin (rDNA);   lepirudin recombinant
 xref: CAS:138068-37-8;   DrugBank:DB00001;   Drug_Central:2995;   KEGG:D06880
 xref_mesh: MESH:C083544
 xref: PMID:15280202;   PMID:19707378;   PMID:22234363;   PMID:28600720;   PMID:29426286;   PMID:8211886;   Pubchem:118856773;   Wikipedia:Lepirudin


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lepirudin term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G F2 coagulation factor II multiple interactions ISO lepirudin binds to and results in decreased activity of F2 protein CTD PMID:15080313, PMID:18449412 NCBI chr 3:80,529,468...80,542,993
Ensembl chr 3:80,529,428...80,543,031
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Term Annotations click to browse term
  CHEBI ontology 19816
    chemical entity 19816
      molecular entity 19814
        polyatomic entity 19727
          macromolecule 3316
            polypeptide 186
              lepirudin 1
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic group 18537
                              organic divalent group 18530
                                organodiyl group 18530
                                  carbonyl group 18436
                                    carbonyl compound 18436
                                      carboxylic acid 18114
                                        carboacyl group 17372
                                          univalent carboacyl group 17372
                                            carbamoyl group 17158
                                              carboxamide 17158
                                                peptide 9396
                                                  cyclic peptide 8723
                                                    heterodetic cyclic peptide 1440
                                                      lepirudin 1
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