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MedKoo Cat#: 599214 | Name: Lophyrotomin

Description:

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

Lophyrotomin is a hepatotoxin isolated from the European Birch sawfly Arge pullata.

Chemical Structure

Lophyrotomin
Lophyrotomin
CAS#85932-85-0

Theoretical Analysis

MedKoo Cat#: 599214

Name: Lophyrotomin

CAS#: 85932-85-0

Chemical Formula: C48H65N9O17

Exact Mass: 1039.4498

Molecular Weight: 1040.09

Elemental Analysis: C, 55.43; H, 6.30; N, 12.12; O, 26.15

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 #
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Synonym
Lophyrotomin;
IUPAC/Chemical Name
benzoyl-D-alanyl-D-phenylalanyl-L-valyl-L-isoleucyl-D-aspartyl-L-aspartyl-D-glutamyl-L-glutamine
InChi Key
YJHPUIVTIUFFBX-WVVKQBIJSA-N
InChi Code
InChI=1S/C48H65N9O17/c1-6-25(4)39(57-46(71)38(24(2)3)56-45(70)31(21-27-13-9-7-10-14-27)53-40(65)26(5)50-41(66)28-15-11-8-12-16-28)47(72)55-33(23-37(63)64)44(69)54-32(22-36(61)62)43(68)51-29(18-20-35(59)60)42(67)52-30(48(73)74)17-19-34(49)58/h7-16,24-26,29-33,38-39H,6,17-23H2,1-5H3,(H2,49,58)(H,50,66)(H,51,68)(H,52,67)(H,53,65)(H,54,69)(H,55,72)(H,56,70)(H,57,71)(H,59,60)(H,61,62)(H,63,64)(H,73,74)/t25-,26+,29+,30-,31+,32-,33+,38-,39-/m0/s1
SMILES Code
OC([C@H](CCC(N)=O)NC([C@@H](CCC(O)=O)NC([C@H](CC(O)=O)NC([C@@H](CC(O)=O)NC([C@H]([C@@H](C)CC)NC([C@H](C(C)C)NC([C@@H](Cc1ccccc1)NC([C@@H](C)NC(c2ccccc2)=O)=O)=O)=O)=O)=O)=O)=O)=O
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,040.09 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: Chong MW, Wong BS, Lam PK, Shaw GR, Seawright AA. Toxicity and uptake mechanism of cylindrospermopsin and lophyrotomin in primary rat hepatocytes. Toxicon. 2002 Feb;40(2):205-11. PubMed PMID: 11689242. 2: Daly NL, Atkins AR, Smith R. Solution structure of the toxic octapeptide, lophyrotomin. Int J Pept Protein Res. 1993 Oct;42(4):366-71. PubMed PMID: 8244631. 3: Kannan R, Oelrichs PB, Thamsborg SM, Williams DH. Identification of the octapeptide lophyrotomin in the European birch sawfly (Arge pullata). Toxicon. 1988;26(2):224-6. PubMed PMID: 3363571. 4: Oelrichs PB, Vallely PJ, Macleod JK, Cable J, Kiely DE, Summons RE. Lophyrotomin, a new toxic octapeptide from the larvae of sawfly, Lophyrotoma interrupta. Lloydia. 1977 Mar-Apr;40(2):209-14. PubMed PMID: 17805. 5: Oelrichs PB, MacLeod JK, Seawright AA, Grace PB. Isolation and identification of the toxic peptides from Lophyrotoma zonalis (Pergidae) sawfly larvae. Toxicon. 2001 Dec;39(12):1933-6. PubMed PMID: 11600157. 6: Boevé JL, Rozenberg R, Shinohara A, Schmidt S. Toxic peptides occur frequently in pergid and argid sawfly larvae. PLoS One. 2014 Aug 14;9(8):e105301. doi: 10.1371/journal.pone.0105301. eCollection 2014. PubMed PMID: 25121515; PubMed Central PMCID: PMC4133368. 7: Petre CA, Detrain C, Boevé JL. Anti-predator defence mechanisms in sawfly larvae of Arge (Hymenoptera, Argidae). J Insect Physiol. 2007 Jul;53(7):668-75. Epub 2007 May 4. PubMed PMID: 17540402. 8: Oelrichs PB, MacLeod JK, Seawright AA, Moore MR, Ng JC, Dutra F, Riet-Corŕea F, Mendez MC, Thamsborg SM. Unique toxic peptides isolated from sawfly larvae in three continents. Toxicon. 1999 Mar;37(3):537-44. PubMed PMID: 10080356. 9: Dutra F, Riet-Correa F, Mendez MC, Paiva N. Poisoning of cattle and sheep in Uruguay by sawfly (Perreyia flavipes) larvae. Vet Hum Toxicol. 1997 Oct;39(5):281-6. PubMed PMID: 9311084.

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