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MedKoo Cat#: 597486 | Name: Lombricine

Description:

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

Lombricine is a phosphagen that is unique to earthworms. Structurally, it is a phosphodiester of 2-guanidinoethanol and D-serine.

Chemical Structure

Lombricine
Lombricine
CAS#18416-85-8

Theoretical Analysis

MedKoo Cat#: 597486

Name: Lombricine

CAS#: 18416-85-8

Chemical Formula: C6H15N4O6P

Exact Mass: 270.0729

Molecular Weight: 270.18

Elemental Analysis: C, 26.67; H, 5.60; N, 20.74; O, 35.53; P, 11.46

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.
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Related CAS #
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Synonym
Lombricine; L-Lombricine;
IUPAC/Chemical Name
O-((2-guanidinoethoxy)(hydroxy)phosphoryl)-L-serine
InChi Key
GSDBGCKBBJVPNC-BYPYZUCNSA-N
InChi Code
InChI=1S/C6H15N4O6P/c7-4(5(11)12)3-16-17(13,14)15-2-1-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H,13,14)(H4,8,9,10)/t4-/m0/s1
SMILES Code
N[C@@H](COP(O)(OCCNC(N)=N)=O)C(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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 270.18 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: Doumen C. Variable intron/exon structure in the oligochaete lombricine kinase gene. Gene. 2012 Sep 1;505(2):276-82. doi: 10.1016/j.gene.2012.06.007. Epub 2012 Jun 12. PubMed PMID: 22705027. 2: Bush DJ, Kirillova O, Clark SA, Davulcu O, Fabiola F, Xie Q, Somasundaram T, Ellington WR, Chapman MS. The structure of lombricine kinase: implications for phosphagen kinase conformational changes. J Biol Chem. 2011 Mar 18;286(11):9338-50. doi: 10.1074/jbc.M110.202796. Epub 2011 Jan 6. PubMed PMID: 21212263; PubMed Central PMCID: PMC3058953. 3: Nagasawa H, Sawaki K, Fujii Y, Kobayashi M, Segawa T, Suzuki R, Inatomi H. Inhibition by lombricine from earthworm (Lumbricus terrestris) of the growth of spontaneous mammary tumours in SHN mice. Anticancer Res. 1991 May-Jun;11(3):1061-4. PubMed PMID: 1909513. 4: Ellington WR, Bush J. Cloning and expression of a lombricine kinase from an echiuroid worm: insights into structural correlates of substrate specificity. Biochem Biophys Res Commun. 2002 Mar 8;291(4):939-44. PubMed PMID: 11866456. 5: Doumen C. cDNA identification, comparison and phylogenetic aspects of lombricine kinase from two oligochaete species. Comp Biochem Physiol B Biochem Mol Biol. 2010 Jun;156(2):137-43. doi: 10.1016/j.cbpb.2010.03.002. Epub 2010 Mar 15. PubMed PMID: 20230902. 6: BEATTY IM, MAGRATH DI, ENNOR AH. Occurrence of D-serine in lombricine. Nature. 1959 Feb 28;183(4661):591. PubMed PMID: 13632801. 7: ROSENBERG H, ROSSITER RJ, GAFFNEY T, ENNOR AH. Lombricine phosphoryltransferase in earthworms. Biochim Biophys Acta. 1960 Jan 15;37:385-6. PubMed PMID: 14438944. 8: BEATTY IM, ENNOR AH, ROSENBERG H, MAGRATH DI. The configuration of the serine moiety of lombricine and reptilian serine ethanolamine phosphodiester. J Biol Chem. 1961 Apr;236:1028-31. PubMed PMID: 13688284. 9: BEATTY IM, MAGRATH DI. Synthesis of DL-and L-lombricine. Nature. 1959 Feb 28;183(4661):591-2. PubMed PMID: 13632802. 10: PANT R. Isolation of lombricine and its enzymic phosphorylation. Biochem J. 1959 Sep;73:30-3. PubMed PMID: 14430183; PubMed Central PMCID: PMC1197007. 11: Suzuki T, Kawasaki Y, Furukohri T, Ellington WR. Evolution of phosphagen kinase. VI. Isolation, characterization and cDNA-derived amino acid sequence of lombricine kinase from the earthworm Eisenia foetida, and identification of a possible candidate for the guanidine substrate recognition site. Biochim Biophys Acta. 1997 Dec 5;1343(2):152-9. PubMed PMID: 9434106. 12: ENNOR AH, ROSENBERG H. The isolation of N-phosphoryl-lombricine from earthworms. Biochem J. 1962 Apr;83:14-7. PubMed PMID: 13890330; PubMed Central PMCID: PMC1243502. 13: BEATTY IM, ENNOR AH, MAGRATH DI. Synthesis of N-phosphoryl-D- and L-lombricine. Nature. 1960 Dec 17;188:1026-7. PubMed PMID: 13688283. 14: ROSENBERG H, ENNOR AH. The isolation of lombricine and its possible biological precursor. Biochem J. 1959 Nov;73:521-6. PubMed PMID: 14438943; PubMed Central PMCID: PMC1197090. 15: ROSSITER RJ, GAFFNEY TJ, ROSENBERG H, ENNOR AH. The formation in vivo of lombricine in the earthworm (Megascolides cameroni). Biochem J. 1960 Sep;76:603-10. PubMed PMID: 13743749; PubMed Central PMCID: PMC1204840. 16: ROSSITER RJ, GAFFNEY T, ROSENBERG H, ENNOR AH. Biosynthesis of lombricine. Nature. 1960 Feb 6;185:383-4. PubMed PMID: 14439305. 17: Gaffney TJ, Rosenberg H, Ennor AH. The purification and properties of adenosine triphosphate-lombricine phosphotransferase. Biochem J. 1964 Jan;90(1):170-6. PubMed PMID: 5832288; PubMed Central PMCID: PMC1202539. 18: Hao J, Liebeke M, Sommer U, Viant MR, Bundy JG, Ebbels TM. Statistical Correlations between NMR Spectroscopy and Direct Infusion FT-ICR Mass Spectrometry Aid Annotation of Unknowns in Metabolomics. Anal Chem. 2016 Mar 1;88(5):2583-9. doi: 10.1021/acs.analchem.5b02889. Epub 2016 Feb 10. PubMed PMID: 26824414. 19: Gaffney TJ, O'Sullivan WJ. Kinetic studies of the activation of adenosine triphosphate-lombricine phosphotransferase by magnesium ions. Biochem J. 1964 Jan;90(1):177-81. PubMed PMID: 5832289; PubMed Central PMCID: PMC1202540. 20: Tsunoda S, Kawamoto H, Inatomi H, Yamamoto K, Nagasawa H. Inhibition by guanidino compounds of the growth of spontaneous mammary tumours in SHN mice. Anticancer Res. 1997 Sep-Oct;17(5A):3349-53. PubMed PMID: 9413171.