(Rac)-SHIN2 is a serine hydroxymethyltransferase (SHMT) inhibitor (antagonist) with a 1,4-dihydropyran[2,3-c]pyrazole structure. (Rac)-SHIN2 participates in the folate or one-carbon metabolic pathway and protects against viral infection. SHMT1 and SHMT2 are the cytosolic and/or mitochondrial isoforms of serine hydroxymethyltransferase, respectively. SHMT1 and SHMT2 are the cytosolic and/or mitochondrial isoforms of serine hydroxymethyltransferase, respectively. (Rac)-SHIN2 is a reagent for click chemistry. It contains Alkyne groups and could undergo CuAAc (copper-catalyzed azide-alkyne cycloaddition reaction) with compounds bearing an Azide group.

Physicochemical Properties

Molecular Formula	C23H26N4O3
Molecular Weight	406.48
Exact Mass	406.2
CAS #	2204289-53-0
Related CAS #	(+)SHIN2;(-)SHIN2
PubChem CID	134335035
Appearance	Light yellow to yellow solid powder
LogP	3.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	30
Complexity	773
Defined Atom Stereocenter Count	0
SMILES	N1=C(C)C2C(C3=CC(C#CCCCO)=CC(CO)=C3)(C(C)C)C(C#N)=C(N)OC=2N1
InChi Key	IWUCUJZMKDHLOF-UHFFFAOYSA-N
InChi Code	InChI=1S/C23H26N4O3/c1-14(2)23(19(12-24)21(25)30-22-20(23)15(3)26-27-22)18-10-16(7-5-4-6-8-28)9-17(11-18)13-29/h9-11,14,28-29H,4,6,8,13,25H2,1-3H3,(H,26,27)
Chemical Name	6-amino-4-[3-(hydroxymethyl)-5-(5-hydroxypent-1-ynyl)phenyl]-3-methyl-4-propan-2-yl-2H-pyrano[2,3-c]pyrazole-5-carbonitrile
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Serine hydroxymethyltransferase (SHMT)[1]
References	[1]. Method of treating and preventing viral infection comprising inhibitors of folate or one-carbon metabolism pathways such as serine hydroxymethyltransferase inhibitors: World Intellectual Property Organization, WO2022120195[P]. 2022-06-09.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (246.01 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4601 mL	12.3007 mL	24.6015 mL
	5 mM	0.4920 mL	2.4601 mL	4.9203 mL
	10 mM	0.2460 mL	1.2301 mL	2.4601 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.