Felinine

Felinine

Names
IUPAC name (2R)-2-Amino-3-[(3-hydroxy-1,1-dimethylpropyl)thio]propanoic acid
Identifiers
CAS Number	471-09-0
ChEBI	CHEBI:39390
ChemSpider	144304
Jmol interactive 3D	Image
PubChem	164607
InChI InChI=1S/C8H17NO3S/c1-8(2,3-4-10)13-5-6(9)7(11)12/h6,10H,3-5,9H2,1-2H3,(H,11,12)/t6-/m0/s1 Key: IFERABFGYYJODC-LURJTMIESA-N InChI=1/C8H17NO3S/c1-8(2,3-4-10)13-5-6(9)7(11)12/h6,10H,3-5,9H2,1-2H3,(H,11,12)/t6-/m0/s1 Key: IFERABFGYYJODC-LURJTMIEBQ
SMILES O=C(O)[C@@H](N)CSC(CCO)(C)C
Properties
Chemical formula	C8H17NO3S
Molar mass	207.29 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Felinine, also known as (R)-2-amino-3-(4-hydroxy-2-methylbutan-2-ylthio)propanoic acid, is a chemical compound and amino acid found in cat urine and a precursor via microbial lyase of the putative cat pheromone and thiol called 3-mercapto-3-methylbutan-1-ol (MMB).^{[1] [2][3]} Felinine is excreted by selected Felidae species including bobcats, Chinese desert cats, the kodkod, and domestic cats. Felinine synthesis occurs in the liver through a condensation reaction of glutathione and isopentenyl pyrophosphate to form 3-mercaptobutanolglutathionine (3-MBG).^[4] In the kidney 3-MBG is hydrolysed and felinine partly acetylated. Cauxin assists in the hydrolysis of the dipeptide (felinylglycine) to increase the concentration of urinary felinine.^[5] Urine of domestic cats may contain a series of felinine-containing compounds including free felinine, acetylfelinine, felinylglycine and 3-MBG.^[6]

See also

• Cat pheromone

References

1. Discovery of felinine: Westall, R. G. "Amino acids and other ampholytes of urine. II. Isolation of a new sulfur-containing amino acid from cat urine" Biochemical Journal (1953), 55, 244-8.
2. W.H. Hendriks, P.J. Moughan, M.F. Tarttelin and A.D. Woolhouse (1995). "Felinine: a urinary amino acid of Felidae". Comp. Biochem. Physiol. 112B (4): 581–588.
3. P. David Josephy (28 January 2006). Molecular Toxicology. Oxford University. p. 376. ISBN 978-0-19-977145-5. Retrieved 29 July 2013.
4. K.J. Rutherfurd, S.M. Rutherfurd, P.J. Moughan and W.H. Hendriks (January 2002). "Isolation and Characterization of a Felinine-containing Peptide from the Blood of the Domestic Cat (Felis catus)". J. Biol. Chem. 277 (1): 114–119. doi:10.1074/jbc.M107728200. PMID 11698402.
5. M. Miyazaki, T. Yamashita, Y. Suzuki, Y. Saito, S. Soeta, H. Taira, and A. Suzuki (October 2006). "A major urinary protein of the domestic cat regulates the production of felinine, a putative pheromone precursor". Chem. Biol. (pdf) 13 (10): 1071–1079. doi:10.1016/j.chembiol.2006.08.013. PMID 17052611.
6. W.H. Hendriks, D.R.K. Harding and K.J. Rutherfurd-Markwick (2004). "Isolation and characterisation of renal metabolites of g-glutamylfelinylglycine in the urine of the domestic cat (Felis catus)". Comp. Biochem. Phys. 139 (2): 245–251. doi:10.1016/j.cbpc.2004.07.007. PMID 15465671.