Moroidin

Moroidin
Names
	IUPAC name (8S,9S,12S,15S,18S,21S,27S)-21-[3-(diaminomethylideneamino)propyl]-12-(2-methylpropyl)-10,13,16,19,22,25-hexaoxo-9-{[(2S)-5-oxopyrrolidine-2-carbonyl]amino}-8,15-di(propan-2-yl)-2,11,14,17,20,23,26,30,32-nonazapentacyclo[16.14.2.13,7.129,32.04,33]hexatriaconta-1(33),3,5,7(36),29(35),30-hexaene-27-carboxylic acid
Identifiers
CAS Number	104041-75-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL385762;
ChemSpider	10356647;
PubChem CID	14311394;
CompTox Dashboard (EPA)	DTXSID901337162 ;
	InChI InChI=1S/C47H66N14O10/c1-21(2)14-31-43(67)59-37(23(5)6)44(68)58-32-17-27-26-10-9-24(36(22(3)4)38(45(69)57-31)60-41(65)29-11-12-34(62)53-29)15-30(26)55-39(27)61-19-25(52-20-61)16-33(46(70)71)54-35(63)18-51-40(64)28(56-42(32)66)8-7-13-50-47(48)49/h9-10,15,19-23,28-29,31-33,36-38,55H,7-8,11-14,16-18H2,1-6H3,(H,51,64)(H,53,62)(H,54,63)(H,56,66)(H,57,69)(H,58,68)(H,59,67)(H,60,65)(H,70,71)(H4,48,49,50)/t28-,29-,31-,32-,33-,36+,37-,38-/m0/s1 Key: UCSHFBQCLZMAJY-QFMFBHDYSA-N;
	SMILES CC(C)C[C@H]1C(=O)N[C@H](C(=O)N[C@H]2Cc3c4ccc(cc4[nH]c3-n5cc(nc5)C[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)CCCNC(=[NH2+])N)C(=O)[O-])[C@H]([C@@H](C(=O)N1)NC(=O)[C@@H]6CCC(=O)N6)C(C)C)C(C)C;
Properties
Chemical formula	C47H66N14O10
Molar mass	987.133 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Moroidin is a biologically active compound found in the plants Dendrocnide moroides and Celosia argentea.^[1] It is a peptide composed of eight amino acids, with unusual leucine-tryptophan and tryptophan-histidine cross-links that form its two rings. Moroidin has been shown to be at least one of several bioactive compounds responsible for the painful sting of the Dendrocnide moroides plant. It also has demonstrated anti-mitotic properties, specifically by inhibition of tubulin polymerization. Anti-mitotic activity gives moroidin potential as a chemotherapy drug, and this property combined with its unusual chemical structure has made it a target for organic synthesis.

^ Morita, Hiroshi; Shimbo, Kazutaka; Shigemori, Hideyuki; Kobayashi, Jun'ichi (March 2000). "Antimitotic activity of moroidin, a bicyclic peptide from the seeds of Celosia argentea". Bioorganic & Medicinal Chemistry Letters. 10 (5): 469–471. doi:10.1016/S0960-894X(00)00029-9. PMID 10743950.

[1] Morita, Hiroshi; Shimbo, Kazutaka; Shigemori, Hideyuki; Kobayashi, Jun'ichi (March 2000). "Antimitotic activity of moroidin, a bicyclic peptide from the seeds of Celosia argentea". Bioorganic & Medicinal Chemistry Letters. 10 (5): 469–471. doi:10.1016/S0960-894X(00)00029-9. PMID 10743950.

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