Felinine
| Felinine |
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(2R)-2-Amino-3-[(3-hydroxy-1,1-dimethylpropyl)thio]propanoic acid
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| Identifiers |
| CAS number |
471-09-0 |
| PubChem |
164607 |
| ChemSpider |
144304 Y |
| ChEBI |
CHEBI:39390 |
| Jmol-3D images |
Image 1 |
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O=C(O)[C@@H](N)CSC(CCO)(C)C
|
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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 Y
Key: IFERABFGYYJODC-LURJTMIESA-N Y
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
|
| Properties |
| Molecular formula |
C8H17NO3S |
| Molar mass |
207.29 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Felinine, also known as (R)-2-amino-3-(4-hydroxy-2-methylbutan-2-ylthio)propanoic acid, is a chemical compound found in cat urine and a precursor of the putative cat pheromone 3-mercapto-3-methylbutan-1-ol (MMB)[1]. 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)[2]. 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 [3]. Urine of domestic cats may contain a series of felinine containing compounds including free felinine, acetylfelinine, felinylglycine and 3-MBG[4].
See also
References
- ^ 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.
- ^ 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.
- ^ 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" (pdf). Chem. Biol. 13 (10): 1071–1079. doi:10.1016/j.chembiol.2006.08.013. PMID 17052611.
- ^ 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.