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MedKoo Cat#: 564130 | Name: SHMT-IN-2
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Description:

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

SHMT-IN-2 is a serine hydroxymethyltransferase (SHMT) inhibitor, potently inhibiting both human SHMT1 and SHMT2. Note: this product was previously named as SHIN2. It is now changed to SHMT-IN-2 so as not to confuse with the SHIN2 published in Leukemia 2021, 35(2):1-12 (web link: https://www.researchgate.net/publication/341220587_SHMT_inhibition_is_effective_and_synergizes_with_methotrexate_in_T-cell_acute_lymphoblastic_leukemia). SHMT-IN-2 was first reported in Proceedings of the National Academy of Sciences of the United States of America, 114(43), 11404-11409; 2017. (Compound 2). This compound can be named as NUN81490 according to MedKoo Chemical Nomenclature (see web page: https://www.medkoo.com/page/naming).

Chemical Structure

SHMT-IN-2
SHMT-IN-2
CAS#2102681-49-0

Theoretical Analysis

MedKoo Cat#: 564130

Name: SHMT-IN-2

CAS#: 2102681-49-0

Chemical Formula: C22H24F3N5O

Exact Mass: 431.1933

Molecular Weight: 431.46

Elemental Analysis: C, 61.24; H, 5.61; F, 13.21; N, 16.23; O, 3.71

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 2,250.00 Ready to ship
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Related CAS #
2102681-49-0 2204289-54-1
Synonym
Serine hydroxymethyltranferase inhibitor 2; SHMT-IN-2; SHIN2; SHIN-2; SHIN 2); NUN81490; NUN-81490; NUN 81490;
IUPAC/Chemical Name
6-Amino-4-isopropyl-3-methyl-4-(3-(pyrrolidin-1-yl)-5-(trifluoromethyl)phenyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
InChi Key
NOKJZHRLDAOFCV-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H24F3N5O/c1-12(2)21(17(11-26)19(27)31-20-18(21)13(3)28-29-20)14-8-15(22(23,24)25)10-16(9-14)30-6-4-5-7-30/h8-10,12H,4-7,27H2,1-3H3,(H,28,29)
SMILES Code
N#CC(C1(C(C)C)C2=CC(C(F)(F)F)=CC(N3CCCC3)=C2)=C(N)OC4=C1C(C)=NN4
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
Biological target:
SHMT-IN-2 is a serine hydroxymethyltransferase (SHMT) inhibitor.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 431.46 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
Formulation protocol:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
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PMID: 34440217; PMCID: PMC8427973. 3: Tramonti A, Cuyàs E, Encinar JA, Pietzke M, Paone A, Verdura S, Arbusà A, Martin-Castillo B, Giardina G, Joven J, Vazquez A, Contestabile R, Cutruzzolà F, Menendez JA. Metformin Is a Pyridoxal-5'-phosphate (PLP)-Competitive Inhibitor of SHMT2. Cancers (Basel). 2021 Aug 9;13(16):4009. doi: 10.3390/cancers13164009. PMID: 34439169; PMCID: PMC8393646. 4: Pikman Y, Ocasio-Martinez N, Alexe G, Dimitrov B, Kitara S, Diehl FF, Robichaud AL, Conway AS, Ross L, Su A, Ling F, Qi J, Roti G, Lewis CA, Puissant A, Vander Heiden MG, Stegmaier K. Targeting serine hydroxymethyltransferases 1 and 2 for T-cell acute lymphoblastic leukemia therapy. Leukemia. 2021 Aug 2. doi: 10.1038/s41375-021-01361-8. Epub ahead of print. PMID: 34341479. 5: Nguyen TH, Vemu PL, Hoy GE, Boudjadi S, Chatterjee B, Shern JF, Khan J, Sun W, Barr FG. Serine hydroxymethyltransferase 2 expression promotes tumorigenesis in rhabdomyosarcoma with 12q13-q14 amplification. 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PMID: 33034447; PMCID: PMC7857146. 13: Tong J, Krieger JR, Taylor P, Bagshaw R, Kang J, Jeedigunta S, Wybenga-Groot LE, Zhang W, Badr H, Mirhadi S, Pham NA, Coyaud É, Yu M, Li M, Cabanero M, Raught B, Maynes JT, Hawkins C, Tsao MS, Moran MF. Cancer proteome and metabolite changes linked to SHMT2. PLoS One. 2020 Sep 9;15(9):e0237981. doi: 10.1371/journal.pone.0237981. PMID: 32903271; PMCID: PMC7480864. 14: Han Y, He L, Qi Y, Zhao Y, Pan Y, Fang B, Li S, Zhang JZH, Zhang L. Identification of three new compounds that directly target human serine hydroxymethyltransferase 2. Chem Biol Drug Des. 2021 Feb;97(2):221-230. doi: 10.1111/cbdd.13774. Epub 2020 Sep 16. PMID: 32779873. 15: Engel AL, Lorenz NI, Klann K, Münch C, Depner C, Steinbach JP, Ronellenfitsch MW, Luger AL. Serine-dependent redox homeostasis regulates glioblastoma cell survival. Br J Cancer. 2020 Apr;122(9):1391-1398. doi: 10.1038/s41416-020-0794-x. Epub 2020 Mar 17. Erratum in: Br J Cancer. 2021 Sep;125(7):1030. PMID: 32203214; PMCID: PMC7188854. 16: Yang L, Garcia Canaveras JC, Chen Z, Wang L, Liang L, Jang C, Mayr JA, Zhang Z, Ghergurovich JM, Zhan L, Joshi S, Hu Z, McReynolds MR, Su X, White E, Morscher RJ, Rabinowitz JD. Serine Catabolism Feeds NADH when Respiration Is Impaired. Cell Metab. 2020 Apr 7;31(4):809-821.e6. doi: 10.1016/j.cmet.2020.02.017. Epub 2020 Mar 17. PMID: 32187526; PMCID: PMC7397714. 17: Li AM, Ducker GS, Li Y, Seoane JA, Xiao Y, Melemenidis S, Zhou Y, Liu L, Vanharanta S, Graves EE, Rankin EB, Curtis C, Massagué J, Rabinowitz JD, Thompson CB, Ye J. Metabolic Profiling Reveals a Dependency of Human Metastatic Breast Cancer on Mitochondrial Serine and One-Carbon Unit Metabolism. Mol Cancer Res. 2020 Apr;18(4):599-611. doi: 10.1158/1541-7786.MCR-19-0606. Epub 2020 Jan 15. PMID: 31941752; PMCID: PMC7127984. 18: Li X, Zhang K, Hu Y, Luo N. ERRα activates SHMT2 transcription to enhance the resistance of breast cancer to lapatinib via modulating the mitochondrial metabolic adaption. Biosci Rep. 2020 Jan 31;40(1):BSR20192465. doi: 10.1042/BSR20192465. PMID: 31894856; PMCID: PMC6970080. 19: Dekhne AS, Ning C, Nayeen MJ, Shah K, Kalpage H, Frühauf J, Wallace-Povirk A, O'Connor C, Hou Z, Kim S, Hüttemann M, Gangjee A, Matherly LH. Cellular Pharmacodynamics of a Novel Pyrrolo[3,2-d]pyrimidine Inhibitor Targeting Mitochondrial and Cytosolic One-Carbon Metabolism. Mol Pharmacol. 2020 Jan;97(1):9-22. doi: 10.1124/mol.119.117937. Epub 2019 Nov 9. PMID: 31707355; PMCID: PMC6877291. 20: He L, Bao J, Yang Y, Dong S, Zhang L, Qi Y, Zhang JZH. Study of SHMT2 Inhibitors and Their Binding Mechanism by Computational Alanine Scanning. J Chem Inf Model. 2019 Sep 23;59(9):3871-3878. doi: 10.1021/acs.jcim.9b00370. Epub 2019 Sep 6. PMID: 31442042.