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MedKoo Cat#: 412943 | Name: Circulin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Circulin A is a macrocyclic knotted peptide having anti-HIV activity.

Chemical Structure

Circulin A
Circulin A
CAS#5854-98-8 (A)

Theoretical Analysis

MedKoo Cat#: 412943

Name: Circulin A

CAS#: 5854-98-8 (A)

Chemical Formula: C53H100N16O13

Exact Mass: 1168.7656

Molecular Weight: 1169.48

Elemental Analysis: C, 54.43; H, 8.62; N, 19.16; O, 17.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
5854-98-8 (A) 20905-50-4 (B)
Synonym
Circulin A
IUPAC/Chemical Name
N-((2S)-4-amino-1-(((3R)-1-(((2S)-4-amino-1-oxo-1-(((3S,6R,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-12-(sec-butyl)-3-(1-hydroxyethyl)-15-isobutyl-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclotricosan-21-yl)amino)butan-2-yl)amino)-3-hydroxy-1-oxobutan-2-yl)amino)-1-oxobutan-2-yl)-6-methyloctanamide
InChi Key
CQLCVUOURZVYSE-FUXMXFBNSA-N
InChi Code
InChI=1S/C53H100N16O13/c1-9-29(5)13-11-12-14-40(72)60-33(15-21-54)48(77)69-43(32(8)71)53(82)65-36(18-24-57)45(74)63-38-20-26-59-51(80)42(31(7)70)68-49(78)37(19-25-58)62-44(73)35(17-23-56)64-52(81)41(30(6)10-2)67-50(79)39(27-28(3)4)66-46(75)34(16-22-55)61-47(38)76/h28-39,41-43,70-71H,9-27,54-58H2,1-8H3,(H,59,80)(H,60,72)(H,61,76)(H,62,73)(H,63,74)(H,64,81)(H,65,82)(H,66,75)(H,67,79)(H,68,78)(H,69,77)/t29?,30?,31?,32-,33+,34+,35+,36+,37-,38+,39-,41+,42+,43?/m1/s1
SMILES Code
CCC(CCCCC(N[C@H](C(NC(C(N[C@H](C(N[C@H]1CCNC([C@H](C(O)C)NC([C@H](NC([C@@H](NC([C@H](C(CC)C)NC([C@H](NC([C@@H](NC1=O)CCN)=O)CC(C)C)=O)=O)CCN)=O)CCN)=O)=O)=O)CCN)=O)[C@H](O)C)=O)CCN)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,169.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Daly NL, Koltay A, Gustafson KR, Boyd MR, Casas-Finet JR, Craik DJ. Solution structure by NMR of circulin A: a macrocyclic knotted peptide having anti-HIV activity. J Mol Biol. 1999 Jan 8;285(1):333-45. doi: 10.1006/jmbi.1998.2276. PMID: 9878410. 2: Balaraman S, Ramalingam R. The structural and functional reliability of Circulins of Chassalia parvifolia for peptide therapeutic scaffolding. J Cell Biochem. 2018 May;119(5):3999-4008. doi: 10.1002/jcb.26557. Epub 2018 Jan 22. PMID: 29231255. 3: Derua R, Gustafson KR, Pannell LK. Analysis of the disulfide linkage pattern in circulin A and B, HIV-inhibitory macrocyclic peptides. Biochem Biophys Res Commun. 1996 Nov 12;228(2):632-8. doi: 10.1006/bbrc.1996.1708. PMID: 8920961. 4: Fujikawa K, Suketa Y, Hayashi K, Suzuki T. Chemical structure of circulin A. Experientia. 1965 Jun 15;21(6):307-8. doi: 10.1007/BF02144681. PMID: 4288271. 5: Craik DJ, Daly NL, Bond T, Waine C. Plant cyclotides: A unique family of cyclic and knotted proteins that defines the cyclic cystine knot structural motif. J Mol Biol. 1999 Dec 17;294(5):1327-36. doi: 10.1006/jmbi.1999.3383. PMID: 10600388. 6: Heitz A, Hernandez JF, Gagnon J, Hong TT, Pham TT, Nguyen TM, Le-Nguyen D, Chiche L. Solution structure of the squash trypsin inhibitor MCoTI-II. A new family for cyclic knottins. Biochemistry. 2001 Jul 10;40(27):7973-83. doi: 10.1021/bi0106639. PMID: 11434766. 7: Studer RO, Lergier W, Vogler K. Synthesen in der Polymyxinreihe 11. Die Synthese von Circulin A [Syntheses in the polymyxin series. 11. Synthesis of circulin A]. Helv Chim Acta. 1966 Mar 10;49(2):974-85. German. doi: 10.1002/hlca.19660490218. PMID: 4286336. 8: Barry DG, Daly NL, Bokesch HR, Gustafson KR, Craik DJ. Solution structure of the cyclotide palicourein: implications for the development of a pharmaceutical framework. Structure. 2004 Jan;12(1):85-94. doi: 10.1016/j.str.2003.11.019. PMID: 14725768. 9: Tam JP, Lu YA, Yang JL, Chiu KW. An unusual structural motif of antimicrobial peptides containing end-to-end macrocycle and cystine-knot disulfides. Proc Natl Acad Sci U S A. 1999 Aug 3;96(16):8913-8. doi: 10.1073/pnas.96.16.8913. PMID: 10430870; PMCID: PMC17707. 10: Trabi M, Svangård E, Herrmann A, Göransson U, Claeson P, Craik DJ, Bohlin L. Variations in cyclotide expression in viola species. J Nat Prod. 2004 May;67(5):806-10. doi: 10.1021/np034068e. PMID: 15165141.