SM-164
SM-164 is a cell-permeable Smac mimetic compound. SM-164 binds to XIAP protein containing both the BIR2 and BIR3 domains with an IC50 value of 1.39 nM and functions as an extremely potent antagonist of XIAP.
Product Specifications
CAS Number
[957135-43-2]
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; IAP
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/SM-164.html
Purity
99.49
Solubility
DMSO : 25 mg/mL (ultrasonic)
Smiles
C[C@H](NC)C(N[C@H]1CCCC[C@](CC[C@H]2C(N[C@@H](C3=CC=CC=C3)C4=CN(CCCCC5=CC=C(CCCCN6N=NC([C@@H](NC([C@@H]7CC[C@@](CCCC[C@@H]8NC([C@@H](NC)C)=O)([H])N7C8=O)=O)C9=CC=CC=C9)=C6)C=C5)N=N4)=O)([H])N2C1=O)=O
Molecular Formula
C62H84N14O6
Molecular Weight
1121.42
Precautions
H302, H315, H319, H335
References & Citations
[1]Sun H, et al. Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J Am Chem Soc. 2007 Dec 12;129 (49) :15279-94.|[2]Lu J, et al. SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP. Cancer Res. 2008 Nov 15;68 (22) :9384-93.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
CIAP; cIAP-1; cIAP-2
Citation 01
Biomater Adv. 2022 Feb:133:112615.|Biomater Adv. 2025 Jan 13:170:214185.|Biomed Res Int. 2019 Apr 7:2019:2121357.|Bioorg Chem. 2023 Aug:137:106647.|Bioorg Chem. 2023 Feb:131:106339.|Bioorg Chem. 2024 Jan:142:106964.|Bioorg Chem. 2025 Jul 1:161:108503.|Bioorg Med Chem. 2023 Aug 15:91:117385.|Bioorg Med Chem. 2024 Feb 15:100:117611.|Bioorg Med Chem. 2024 Mar 15:102:117659.|bioRxiv. 2023 Apr 25.|bioRxiv. 2023 Aug 24.|Cancer Cell. 2025 May 12;43 (5) :955-969.e10.|Cell Death Dis. 2024 Oct 18;15 (10) :759.|Cell Death Dis. 2025 Jun 17;16 (1) :452.|Cell Death Dis. 2025 Oct 24;16 (1) :759.|Cell Death Dis. 2018 Nov 15;9 (12) :1140. |Cell Death Discov. 2024 Mar 23;10 (1) :152.|Cell Death Discov. 2025 Jul 25;11 (1) :345.|Cell Rep. 2025 Aug 21;44 (9) :116186.|Cell Res. 2023 Nov;33 (11) :835-850.|Cell. 2025 Dec 11;188 (25) :7155-7174.e25.|Curr Protoc. 2021 Jun;1 (6) :e156.|Eur J Med Chem. 2021 Aug 5:220:113484.|Eur J Med Chem. 2022 Jun 5;236:114345.|Eur J Med Chem. 2024 Apr 5:269:116304.|Georg Thieme Verlag KG|Int J Biol Macromol. 2023 Jul 31:244:125373.|J Cell Mol Med. 2024 Mar;28 (5) :e17929.|J Inflamm Res. 2025 Jul 19:18:9587-9608.|J Med Chem. 2022 Nov 10;65 (21) :14957-14969.|J Med Chem. 2023 Apr 13;66 (7) :5261-5278.|J Med Chem. 2023 Feb 23;66 (4) :3073-3087.|J Med Chem. 2025 Dec 11;68 (23) :25590-25606.|J Med Chem. 2025 May 22;68 (10) :9906-9925.|JCI Insight. 2025 Oct 22;10 (20) :e180655.|Mol Neurobiol. 2023 Apr;60 (4) :2135-2149.|Nat Commun. 2025 Aug 7;16 (1) :7309.|Nature. 2024 Apr;628 (8009) :835-843.|Oncoimmunology. 2025 Dec;14 (1) :2490346.|Patent. US20230192662A1.|Patent. US20240217963A1.|Patent. US20240294508A1.|PLoS Pathog. 2024 Aug 30;20 (8) :e1012387.|Proc Natl Acad Sci U S A. 2022 Sep 6;119 (36) :e2117396119.|Res Sq. 2025 Jul 16.|Res Sq. 2025 Jul 20.|Research Square Print. 2022 May.|Rheumatology (Oxford) . 2023 Jul 5;62 (7) :2563-2573.|Sci Immunol. 2024 Jul 12;9 (97) :eadn0178.|Signal Transduct Target Ther. 2020 Oct 9;5 (1) :235.|J Ethnopharmacol. 2024 Jan 30;319 (Pt 3) :117373.|Mol Med Rep. 2025 Jun;31 (6) :153.
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