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MedKoo Cat#: 596199 | Name: DMP 323

Description:

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

DMP 323 is a potent HIV-1 protease inhibitor.

Chemical Structure

DMP 323
DMP 323
CAS#151867-81-1

Theoretical Analysis

MedKoo Cat#: 596199

Name: DMP 323

CAS#: 151867-81-1

Chemical Formula: C35H38N2O5

Exact Mass: 566.2781

Molecular Weight: 566.69

Elemental Analysis: C, 74.18; H, 6.76; N, 4.94; O, 14.12

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
DMP 323; DMP-323; DMP323; JCR 424; JCR424; JCR-424; XM 323; XM323; XM-323;
IUPAC/Chemical Name
(4S,5R,6R,7S)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis(4-(hydroxymethyl)benzyl)-1,3-diazepan-2-one
InChi Key
XCVGQMUMMDXKCY-PSWJWLENSA-N
InChi Code
InChI=1S/C35H38N2O5/c38-23-29-15-11-27(12-16-29)21-36-31(19-25-7-3-1-4-8-25)33(40)34(41)32(20-26-9-5-2-6-10-26)37(35(36)42)22-28-13-17-30(24-39)18-14-28/h1-18,31-34,38-41H,19-24H2/t31-,32-,33+,34+/m0/s1
SMILES Code
O=C1N(CC2=CC=C(CO)C=C2)[C@@H](CC3=CC=CC=C3)[C@@H](O)[C@H](O)[C@H](CC4=CC=CC=C4)N1CC5=CC=C(CO)C=C5
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 566.69 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: Singh N, Frushicheva MP, Warshel A. Validating the vitality strategy for fighting drug resistance. Proteins. 2012 Apr;80(4):1110-22. doi: 10.1002/prot.24012. Epub 2012 Jan 31. PubMed PMID: 22275047; PubMed Central PMCID: PMC3299486. 2: Ishikita H, Warshel A. Predicting drug-resistant mutations of HIV protease. Angew Chem Int Ed Engl. 2008;47(4):697-700. PubMed PMID: 18058968. 3: Vilar S, Villaverde MC, Sussman F. Inhibitor docking screened by the modified SAFE_p scoring function: application to cyclic urea HIV-1 PR inhibitors. J Comput Chem. 2007 Oct;28(13):2216-25. PubMed PMID: 17450567. 4: Richter M, Gyémánt N, Molnár J, Hilgeroth A. P-glycoprotein effects of cyclic urea HIV protease inhibitor DMP 323 in competitional absorption studies. Arch Pharm (Weinheim). 2006 Nov;339(11):625-8. PubMed PMID: 17048292. 5: Hylton KG, Main AD, McElwee-White L. Catalytic carbonylation of functionalized diamines: application to the core structure of DMP 323 and DMP 450. J Org Chem. 2003 Feb 21;68(4):1615-7. PubMed PMID: 12585919. 6: McReynolds MD, Sprott KT, Hanson PR. A concise route to structurally diverse DMP 323 analogues via highly functionalized 1,4-diamines. Org Lett. 2002 Dec 26;4(26):4673-6. PubMed PMID: 12489958. 7: Fehér A, Weber IT, Bagossi P, Boross P, Mahalingam B, Louis JM, Copeland TD, Torshin IY, Harrison RW, Tözsér J. Effect of sequence polymorphism and drug resistance on two HIV-1 Gag processing sites. Eur J Biochem. 2002 Aug;269(16):4114-20. PubMed PMID: 12180988. 8: Ishima R, Ghirlando R, Tözsér J, Gronenborn AM, Torchia DA, Louis JM. Folded monomer of HIV-1 protease. J Biol Chem. 2001 Dec 28;276(52):49110-6. Epub 2001 Oct 11. PubMed PMID: 11598128. 9: Wang L, Duan Y, Stouten P, De Lucca GV, Klabe RM, Kollman PA. Does a diol cyclic urea inhibitor of HIV-1 protease bind tighter than its corresponding alcohol form? A study by free energy perturbation and continuum electrostatics calculations. J Comput Aided Mol Des. 2001 Feb;15(2):145-56. PubMed PMID: 11272701. 10: Bahmani MK, Kameoka M, Goto T, Sano K, Luftig RB, Ikuta K. Fusion of uninfected T-cells occurs with immature HIV-1 protease-mutant, but not morphologically similar protease inhibitor derived particles. Virus Res. 2000 Feb;66(2):131-7. PubMed PMID: 10725546. 11: Ishima R, Freedberg DI, Wang YX, Louis JM, Torchia DA. Flap opening and dimer-interface flexibility in the free and inhibitor-bound HIV protease, and their implications for function. Structure. 1999 Sep 15;7(9):1047-55. PubMed PMID: 10508781. 12: Ishima R, Louis JM, Torchia DA. Transverse 1H cross relaxation in 1H-15N correlated 1H CPMG experiments. J Magn Reson. 1999 Mar;137(1):289-92. PubMed PMID: 10053163. 13: Patel M, Bacheler LT, Rayner MM, Cordova BC, Klabe RM, Erickson-Viitanen S, Seitz SP. The synthesis and evaluation of cyclic ureas as HIV protease inhibitors: modifications of the P1/P1' residues. Bioorg Med Chem Lett. 1998 Apr 7;8(7):823-8. PubMed PMID: 9871548. 14: Ala PJ, Huston EE, Klabe RM, Jadhav PK, Lam PY, Chang CH. Counteracting HIV-1 protease drug resistance: structural analysis of mutant proteases complexed with XV638 and SD146, cyclic urea amides with broad specificities. Biochemistry. 1998 Oct 27;37(43):15042-9. PubMed PMID: 9790666. 15: De Lucca GV, Jadhav PK, Waltermire RE, Aungst BJ, Erickson-Viitanen S, Lam PY. De novo design and discovery of cyclic HIV protease inhibitors capable of displacing the active-site structural water molecule. Pharm Biotechnol. 1998;11:257-84. Review. PubMed PMID: 9760684. 16: Ala PJ, DeLoskey RJ, Huston EE, Jadhav PK, Lam PY, Eyermann CJ, Hodge CN, Schadt MC, Lewandowski FA, Weber PC, McCabe DD, Duke JL, Chang CH. Molecular recognition of cyclic urea HIV-1 protease inhibitors. J Biol Chem. 1998 May 15;273(20):12325-31. PubMed PMID: 9575185. 17: De Lucca GV, Kim UT, Liang J, Cordova B, Klabe RM, Garber S, Bacheler LT, Lam GN, Wright MR, Logue KA, Erickson-Viitanen S, Ko SS, Trainor GL. Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues. J Med Chem. 1998 Jun 18;41(13):2411-23. PubMed PMID: 9632373. 18: Marrone TJ, Resat H, Hodge CN, Chang CH, McCammon JA. Solvation studies of DMP323 and A76928 bound to HIV protease: analysis of water sites using grand canonical Monte Carlo simulations. Protein Sci. 1998 Mar;7(3):573-9. PubMed PMID: 9541388; PubMed Central PMCID: PMC2143944. 19: Nillroth U, Vrang L, Markgren PO, Hultén J, Hallberg A, Danielson UH. Human immunodeficiency virus type 1 proteinase resistance to symmetric cyclic urea inhibitor analogs. Antimicrob Agents Chemother. 1997 Nov;41(11):2383-8. PubMed PMID: 9371337; PubMed Central PMCID: PMC164132. 20: Hultén J, Bonham NM, Nillroth U, Hansson T, Zuccarello G, Bouzide A, Aqvist J, Classon B, Danielson UH, Karlén A, Kvarnström I, Samuelsson B, Hallberg A. Cyclic HIV-1 protease inhibitors derived from mannitol: synthesis, inhibitory potencies, and computational predictions of binding affinities. J Med Chem. 1997 Mar 14;40(6):885-97. PubMed PMID: 9083477.