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MedKoo Cat#: 597777 | Name: Pepticinnamin E

Description:

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

Pepticinnamin E is a naturally occurring bisubstrate inhibitor of farnesyltransferase.

Chemical Structure

Pepticinnamin E
Pepticinnamin E
CAS#147317-36-0

Theoretical Analysis

MedKoo Cat#: 597777

Name: Pepticinnamin E

CAS#: 147317-36-0

Chemical Formula: C49H54ClN5O10

Exact Mass: 907.3559

Molecular Weight: 908.44

Elemental Analysis: C, 64.79; H, 5.99; Cl, 3.90; N, 7.71; O, 17.61

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 #
No Data
Synonym
Pepticinnamin E;
IUPAC/Chemical Name
((R)-3,6-dioxopiperazin-2-yl)methyl N-((S)-3-(2-chloro-3-hydroxy-4-methoxyphenyl)-2-((R)-3-(4-hydroxyphenyl)-N-methyl-2-((E)-3-(2-((Z)-pent-1-en-1-yl)phenyl)acrylamido)propanamido)propanoyl)-N-methyl-L-phenylalaninate
InChi Key
FAVCPKLIWNVVMG-AGJVLQOFSA-N
InChi Code
InChI=1S/C49H54ClN5O10/c1-5-6-8-15-33-16-11-12-17-34(33)21-25-42(57)52-37(26-32-18-22-36(56)23-19-32)47(61)54(2)39(28-35-20-24-41(64-4)45(59)44(35)50)48(62)55(3)40(27-31-13-9-7-10-14-31)49(63)65-30-38-46(60)51-29-43(58)53-38/h7-25,37-40,56,59H,5-6,26-30H2,1-4H3,(H,51,60)(H,52,57)(H,53,58)/b15-8-,25-21+/t37-,38-,39+,40+/m1/s1
SMILES Code
O=C(OC[C@H](C(NC1)=O)NC1=O)[C@H](CC2=CC=CC=C2)N(C([C@H](CC3=CC=C(OC)C(O)=C3Cl)N(C)C([C@@H](CC4=CC=C(O)C=C4)NC(/C=C/C5=CC=CC=C5/C=C\CCC)=O)=O)=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
>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 908.44 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: Thutewohl M, Waldmann H. Solid-phase synthesis of a pepticinnamin E library. Bioorg Med Chem. 2003 Jun 12;11(12):2591-615. PubMed PMID: 12757726. 2: Shiomi K, Yang H, Inokoshi J, Van der Pyl D, Nakagawa A, Takeshima H, Omura S. Pepticinnamins, new farnesyl-protein transferase inhibitors produced by an actinomycete. II. Structural elucidation of pepticinnamin E. J Antibiot (Tokyo). 1993 Feb;46(2):229-34. PubMed PMID: 8468236. 3: Thutewohl M, Kissau L, Popkirova B, Karaguni IM, Nowak T, Bate M, Kuhlmann J, Müller O, Waldmann H. Identification of mono- and bisubstrate inhibitors of protein farnesyltransferase and inducers of apoptosis from a pepticinnamin E library. Bioorg Med Chem. 2003 Jun 12;11(12):2617-26. PubMed PMID: 12757727. 4: Hinterding K, Hagenbuch P, Rétey J, Waldmann H. Synthesis and In Vitro Evaluation of the Ras Farnesyltransferase Inhibitor Pepticinnamin E. Angew Chem Int Ed Engl. 1998 May 18;37(9):1236-1239. doi: 10.1002/(SICI)1521-3773(19980518)37:9<1236::AID-ANIE1236>3.0.CO;2-F. PubMed PMID: 29711232. 5: Tan KT, Guiu-Rozas E, Bon RS, Guo Z, Delon C, Wetzel S, Arndt S, Alexandrov K, Waldmann H, Goody RS, Wu YW, Blankenfeldt W. Design, synthesis, and characterization of peptide-based rab geranylgeranyl transferase inhibitors. J Med Chem. 2009 Dec 24;52(24):8025-37. doi: 10.1021/jm901117d. PubMed PMID: 19894725. 6: Thutewohl M, Kissau L, Popkirova B, Karaguni IM, Nowak T, Bate M, Kuhlmann J, Müller O, Waldmann H. Solid-phase synthesis and biological evaluation of a pepticinnamin E library. Angew Chem Int Ed Engl. 2002 Oct 4;41(19):3616-20; 3516. PubMed PMID: 12370908. 7: Omura S, Van der Pyl D, Inokoshi J, Takahashi Y, Takeshima H. Pepticinnamins, new farnesyl-protein transferase inhibitors produced by an actinomycete. I. Producing strain, fermentation, isolation and biological activity. J Antibiot (Tokyo). 1993 Feb;46(2):222-8. PubMed PMID: 8468235. 8: Takeshima H, Omura S. [Inhibitor for protein-farnesylation]. Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1695-703. Review. Japanese. PubMed PMID: 7692468.

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