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Cycloviolacin Y5

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Cycloviolacin Y5 was found in Viola philippica. It has antiviral activity.

Category

Functional Peptides

Catalog number

BAT-012369

Molecular Formula

C132H209N33O42S6

Molecular Weight

3122.7

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2R)-2-[[(2S)-1-[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-3-sulfanylpropanoyl]amino]propanoyl]amino]-5-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[(2S)-2-[[(2R)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

Cycloviolacin Y5

Sequence

GIPCAESCVWIPCTVTAIVGCSCSDKVCYN

InChI

InChI=1S/C132H209N33O42S6/c1-19-63(13)101(156-93(173)46-134)130(204)164-39-25-30-90(164)122(196)153-85(53-209)116(190)138-65(15)105(179)141-75(36-37-95(175)176)107(181)148-82(50-167)114(188)152-88(56-212)120(194)159-98(60(7)8)125(199)146-78(43-70-47-136-73-28-22-21-27-72(70)73)112(186)161-102(64(14)20-2)131(205)165-40-26-31-91(165)123(197)154-89(57-213)121(195)162-104(68(18)170)129(203)160-100(62(11)12)127(201)163-103(67(17)169)128(202)139-66(16)106(180)143-76(41-58(3)4)111(185)157-97(59(5)6)124(198)137-48-94(174)140-84(52-208)117(191)149-83(51-168)115(189)151-86(54-210)119(193)150-81(49-166)113(187)145-79(45-96(177)178)110(184)142-74(29-23-24-38-133)108(182)158-99(61(9)10)126(200)155-87(55-211)118(192)144-77(42-69-32-34-71(171)35-33-69)109(183)147-80(132(206)207)44-92(135)172/h21-22,27-28,32-35,47,58-68,74-91,97-104,136,166-171,208-213H,19-20,23-26,29-31,36-46,48-57,133-134H2,1-18H3,(H2,135,172)(H,137,198)(H,138,190)(H,139,202)(H,140,174)(H,141,179)(H,142,184)(H,143,180)(H,144,192)(H,145,187)(H,146,199)(H,147,183)(H,148,181)(H,149,191)(H,150,193)(H,151,189)(H,152,188)(H,153,196)(H,154,197)(H,155,200)(H,156,173)(H,157,185)(H,158,182)(H,159,194)(H,160,203)(H,161,186)(H,162,195)(H,163,201)(H,175,176)(H,177,178)(H,206,207)/t63-,64-,65-,66-,67+,68+,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,97-,98-,99-,100-,101-,102-,103-,104-/m0/s1

InChI Key

RAQOZXKCAVHDCK-BTBSYRIQSA-N

Canonical SMILES

CCC(C)C(C(=O)N1CCCC1C(=O)NC(CS)C(=O)NC(C)C(=O)NC(CCC(=O)O)C(=O)NC(CO)C(=O)NC(CS)C(=O)NC(C(C)C)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)NC(C(C)CC)C(=O)N4CCCC4C(=O)NC(CS)C(=O)NC(C(C)O)C(=O)NC(C(C)C)C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CS)C(=O)NC(CO)C(=O)NC(CS)C(=O)NC(CO)C(=O)NC(CC(=O)O)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CS)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)NC(CC(=O)N)C(=O)O)NC(=O)CN

1. Anti-HIV cyclotides from the Chinese medicinal herb Viola yedoensis

Conan K L Wang, Michelle L Colgrave, Kirk R Gustafson, David C Ireland, Ulf Goransson, David J Craik J Nat Prod. 2008 Jan;71(1):47-52. doi: 10.1021/np070393g. Epub 2007 Dec 15.

Cyclotides are macrocyclic plant peptides characterized by a knotted arrangement of three disulfide bonds. They display a range of interesting bioactivities, including anti-HIV and insecticidal activities. More than 100 different cyclotides have been isolated from two phylogenetically distant plant families, the Rubiaceae and Violaceae. In this study we have characterized the cyclotides from Viola yedoensis, an important Chinese herb from the Violaceae family that has been reported to contain potential anti-HIV agents. From V. yedoensis five new and three known cyclotides were identified and shown to have anti-HIV activity. The most active of these is cycloviolacin Y5, which is one of the most potent of all cyclotides tested so far using in vitro XTT-based anti-HIV assays. Cycloviolacin Y5 is the most hydrophobic of the cyclotides from V. yedoensis. We show that there is a positive correlation between the hydrophobicity and the anti-HIV activity of the new cyclotides and that this trend tracks with their ability to disrupt membranes, as judged from hemolytic assays on human erythrocytes.

2. [A cyclotide against influenza A H1N1 virus from Viola yedoensis]

Min-Zhi Liu, Yan Yang, Shu-Xiang Zhang, Liang Tang, Hui-Min Wang, Cheng-Juan Chen, Zhu-Fang Shen, Ke-Di Cheng, Jian-Qiang Kong, Wei Wang Yao Xue Xue Bao. 2014 Jun;49(6):905-12.

Three cyclotides were isolated from the whole plant of Viola yedoensis in this study. The two, vary peptide E and cycloviolacin Y5, were previously reported, and a novel cycloviolacin VY1 was characterized according to the interpretation of MS/MS fragmentation of peptides which were produced from the reduced and alkylated parent peptide with the digestion of Endo Lys-C, trypsin and chymotrypsin, separately. The stability of remarkable resistance to proteolytic degradation by trypsin and chymotrypsin, and that of thermal denaturation was confirmed again. Besides, the IC50 value of cycloviolacin VY1 against influenza A H1N1 virus was (2.27 +/- 0.20) microg x mL(-1). It is the first cyclotide reported with anti-influenza A H1N1 virus activity in vitro assay.