MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 596914 | Name: Sparfosic Acid

Description:

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

Sparfosic Acid is an inhibitor of aspartate transcarbamylase; bisubstrate ligand.

Chemical Structure

Sparfosic Acid
Sparfosic Acid
CAS#51321-79-0

Theoretical Analysis

MedKoo Cat#: 596914

Name: Sparfosic Acid

CAS#: 51321-79-0

Chemical Formula: C6H10NO8P

Exact Mass: 255.0144

Molecular Weight: 255.11

Elemental Analysis: C, 28.25; H, 3.95; N, 5.49; O, 50.17; P, 12.14

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Sparfosic Acid; Acide sparfosique; NSC-224131; NSC 224131; NSC224131; N-Phosphonacetyl-L-aspartate;
IUPAC/Chemical Name
(2-phosphonoacetyl)-L-aspartic acid
InChi Key
ZZKNRXZVGOYGJT-VKHMYHEASA-N
InChi Code
InChI=1S/C6H10NO8P/c8-4(2-16(13,14)15)7-3(6(11)12)1-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)(H2,13,14,15)/t3-/m0/s1
SMILES Code
O=C(O)C[C@@H](C(O)=O)NC(CP(O)(O)=O)=O
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 255.11 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: Ruiz-Ramos A, Velázquez-Campoy A, Grande-García A, Moreno-Morcillo M, Ramón-Maiques S. Structure and Functional Characterization of Human Aspartate Transcarbamoylase, the Target of the Anti-tumoral Drug PALA. Structure. 2016 Jul 6;24(7):1081-94. doi: 10.1016/j.str.2016.05.001. Epub 2016 Jun 2. PubMed PMID: 27265852. 2: Wang J, Yin H, Panandikar A, Gandhi V, Sen S. Elevated cyclin A associated kinase activity promotes sensitivity of metastatic human cancer cells to DNA antimetabolite drug. Int J Oncol. 2015 Aug;47(2):782-90. doi: 10.3892/ijo.2015.3037. Epub 2015 Jun 8. PubMed PMID: 26058363; PubMed Central PMCID: PMC4501665. 3: Ruiz-Ramos A, Lallous N, Grande-García A, Ramón-Maiques S. Expression, purification, crystallization and preliminary X-ray diffraction analysis of the aspartate transcarbamoylase domain of human CAD. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 Dec;69(Pt 12):1425-30. doi: 10.1107/S1744309113031114. Epub 2013 Nov 29. PubMed PMID: 24316846; PubMed Central PMCID: PMC3855736. 4: Yan B, Ouyang R, Huang C, Liu F, Neill D, Li C, Dewhirst M. Heat induces gene amplification in cancer cells. Biochem Biophys Res Commun. 2012 Oct 26;427(3):473-7. doi: 10.1016/j.bbrc.2012.09.011. Epub 2012 Sep 11. PubMed PMID: 22975353. 5: Ruhul Amin AR, Thakur VS, Gupta K, Agarwal MK, Wald DN, Shin DM, Agarwal ML. N-(phosphonacetyl)-L-aspartate induces TAp73-dependent apoptosis by modulating multiple Bcl-2 proteins: potential for cancer therapy. Oncogene. 2013 Feb 14;32(7):920-9. doi: 10.1038/onc.2012.96. Epub 2012 Mar 19. PubMed PMID: 22430213; PubMed Central PMCID: PMC3382011. 6: Yang Y, Cai S, Yang L, Yu S, Jiang J, Yan X, Zhang H, Liu L, Liu Q, Du J, Cai S, Sung KL. Targeting eradication of malignant cells derived from human bone marrow mesenchymal stromal cells. Exp Cell Res. 2010 Dec 10;316(20):3329-41. doi: 10.1016/j.yexcr.2010.02.014. Epub 2010 Feb 23. PubMed PMID: 20184882. 7: Coudray L, Kantrowitz ER, Montchamp JL. Submicromolar phosphinic inhibitors of Escherichia coli aspartate transcarbamoylase. Bioorg Med Chem Lett. 2009 Feb 1;19(3):900-2. doi: 10.1016/j.bmcl.2008.11.115. Epub 2008 Dec 6. PubMed PMID: 19097895; PubMed Central PMCID: PMC2743340. 8: Hastak K, Paul RK, Agarwal MK, Thakur VS, Amin AR, Agrawal S, Sramkoski RM, Jacobberger JW, Jackson MW, Stark GR, Agarwal ML. DNA synthesis from unbalanced nucleotide pools causes limited DNA damage that triggers ATR-CHK1-dependent p53 activation. Proc Natl Acad Sci U S A. 2008 Apr 29;105(17):6314-9. doi: 10.1073/pnas.0802080105. Epub 2008 Apr 23. PubMed PMID: 18434539; PubMed Central PMCID: PMC2359797. 9: Mathew R, Kongara S, Beaudoin B, Karp CM, Bray K, Degenhardt K, Chen G, Jin S, White E. Autophagy suppresses tumor progression by limiting chromosomal instability. Genes Dev. 2007 Jun 1;21(11):1367-81. Epub 2007 May 17. Erratum in: Genes Dev. 2007 Jul 1;21(13):1701. PubMed PMID: 17510285; PubMed Central PMCID: PMC1877749. 10: Eldo J, Heng S, Kantrowitz ER. Design, synthesis, and bioactivity of novel inhibitors of E. coli aspartate transcarbamoylase. Bioorg Med Chem Lett. 2007 Apr 1;17(7):2086-90. Epub 2006 Dec 21. PubMed PMID: 17336518; PubMed Central PMCID: PMC1930159. 11: Agarwal MK, Hastak K, Jackson MW, Breit SN, Stark GR, Agarwal ML. Macrophage inhibitory cytokine 1 mediates a p53-dependent protective arrest in S phase in response to starvation for DNA precursors. Proc Natl Acad Sci U S A. 2006 Oct 31;103(44):16278-83. Epub 2006 Oct 18. PubMed PMID: 17050687; PubMed Central PMCID: PMC1637573. 12: Unger MM, Wahl J, Ushmorov A, Buechele B, Simmet T, Debatin KM, Beltinger C. Enriching suicide gene bearing tumor cells for an increased bystander effect. Cancer Gene Ther. 2007 Jan;14(1):30-8. Epub 2006 Oct 6. PubMed PMID: 17024230. 13: Zanotti JM, Hervé G, Bellissent-Funel MC. Picosecond dynamics of T and R forms of aspartate transcarbamylase: a neutron scattering study. Biochim Biophys Acta. 2006 Oct;1764(10):1527-35. Epub 2006 Aug 24. PubMed PMID: 17008138. 14: Eldo J, Cardia JP, O'Day EM, Xia J, Tsuruta H, Kantrowitz ER. N-phosphonacetyl-L-isoasparagine a potent and specific inhibitor of Escherichia coli aspartate transcarbamoylase. J Med Chem. 2006 Oct 5;49(20):5932-8. PubMed PMID: 17004708; PubMed Central PMCID: PMC2538380. 15: Rebuzzini P, Martinelli P, Blasco M, Giulotto E, Mondello C. Inhibition of gene amplification in telomerase deficient immortalized mouse embryonic fibroblasts. Carcinogenesis. 2007 Mar;28(3):553-9. Epub 2006 Sep 14. PubMed PMID: 16973670. 16: Leonard GD, Kemeny NE. Continued survival of more than ten years, without resection of metastatic disease, in patients with metastatic colorectal cancer treated with biomodulated fluorouracil: report of two cases. Dis Colon Rectum. 2006 Mar;49(3):407-10. PubMed PMID: 16475032. 17: Garcia RA, Liu L, Hu Z, Gonzalez A, von Borstel RW, Saydoff JA. Severe cytochrome c oxidase inhibition in vivo does not induce a pyrimidine deficiency; neuroprotective action of oral uridine prodrug PN401 requires supraphysiological levels of uridine. Brain Res. 2005 Dec 20;1066(1-2):164-71. Epub 2005 Dec 5. PubMed PMID: 16330000. 18: Pfund E, Lequeux T, Masson S, Vazeux M, Cordi A, Pierre A, Serre V, Hervé G. Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity. Bioorg Med Chem. 2005 Aug 15;13(16):4921-8. PubMed PMID: 15975800. 19: Stieglitz KA, Pastra-Landis SC, Xia J, Tsuruta H, Kantrowitz ER. A single amino acid substitution in the active site of Escherichia coli aspartate transcarbamoylase prevents the allosteric transition. J Mol Biol. 2005 Jun 3;349(2):413-23. Epub 2005 Apr 9. PubMed PMID: 15890205; PubMed Central PMCID: PMC1479453. 20: Hollander MC, Philburn RT, Patterson AD, Wyatt MA, Fornace AJ Jr. Genomic instability in Gadd45a-/- cells is coupled with S-phase checkpoint defects. Cell Cycle. 2005 May;4(5):704-9. Epub 2005 May 14. PubMed PMID: 15846075.

View History

Spantide II

Spantide II