Tubercidin 5'-triphosphate

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

MedKoo CAT#: 462584

CAS#: 10058-66-9

Description: Tubercidin 5'-triphosphate, an ATP analog, is a substrate for the mitochondrial phosphotransferases from rat liver and beef heart.

Chemical Structure

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Tubercidin 5'-triphosphate
CAS# 10058-66-9
Instruction

Theoretical Analysis

MedKoo Cat#: 462584
Name: Tubercidin 5'-triphosphate
CAS#: 10058-66-9
Chemical Formula: C11H17N4O13P3
Exact Mass: 506.00
Molecular Weight: 506.193
Elemental Analysis: C, 26.10; H, 3.39; N, 11.07; O, 41.09; P, 18.36

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Tubercidin 5'-triphosphate

IUPAC/Chemical Name: 5-(5-O-(Hydroxy((hydroxy(phosphonooxy)phosphinyl)oxy)phosphinyl)-beta-D-ribofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-amine

InChi Key: GVVRDIINMFAFEO-KCGFPETGSA-N

InChi Code: InChI=1S/C11H17N4O13P3/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(17)7(16)6(26-11)3-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,4,6-8,11,16-17H,3H2,(H,21,22)(H,23,24)(H2,12,13,14)(H2,18,19,20)/t6-,7-,8-,11-/m1/s1

SMILES Code: Nc1ncnc2c1ccn2[C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]3O

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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 506.19 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:
In vitro protocol:
In vivo protocol:

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13: Zhao LX, Huang SX, Tang SK, Jiang CL, Duan Y, Beutler JA, Henrich CJ, McMahon JB, Schmid T, Blees JS, Colburn NH, Rajski SR, Shen B. Actinopolysporins A-C and tubercidin as a Pdcd4 stabilizer from the halophilic actinomycete Actinopolyspora erythraea YIM 90600. J Nat Prod. 2011 Sep 23;74(9):1990-5. doi: 10.1021/np200603g. Epub 2011 Aug 26. PMID: 21870828; PMCID: PMC3179765.

14: Kazimierczuk Z, Revankar GR, Robins RK. Total synthesis of certain 2-, 6-mono- and 2,6-disubstituted-tubercidin derivatives. Synthesis of tubercidin via the sodium salt glycosylation procedure. Nucleic Acids Res. 1984 Jan 25;12(2):1179-92. doi: 10.1093/nar/12.2.1179. PMID: 6694909; PMCID: PMC318564.

15: Sandau US, Yahya M, Bigej R, Friedman JL, Saleumvong B, Boison D. Transient use of a systemic adenosine kinase inhibitor attenuates epilepsy development in mice. Epilepsia. 2019 Apr;60(4):615-625. doi: 10.1111/epi.14674. Epub 2019 Feb 27. PMID: 30815855; PMCID: PMC6713278.

16: Seela F, Peng X, Eickmeier H, Reuter H. 2-Amino-7-chloro-2'-deoxytubercidin. Acta Crystallogr C. 2006 Oct;62(Pt 10):o593-5. doi: 10.1107/S0108270106032227. Epub 2006 Sep 12. PMID: 17008745.

17: Aoki JI, Coelho AC, Muxel SM, Zampieri RA, Sanchez EM, Nerland AH, Floeter- Winter LM, Cotrim PC. Characterization of a Novel Endoplasmic Reticulum Protein Involved in Tubercidin Resistance in Leishmania major. PLoS Negl Trop Dis. 2016 Sep 8;10(9):e0004972. doi: 10.1371/journal.pntd.0004972. PMID: 27606425; PMCID: PMC5015992.

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20: Nishimura N, Kato A, Maeba I. Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin. Carbohydr Res. 2001 Mar 9;331(1):77-82. doi: 10.1016/s0008-6215(01)00017-9. PMID: 11284507.