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Identification
YMDB IDYMDB00726
NameN-Formyl-L-tyrosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-Formyl-L-tyrosine belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-tyrosine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Formyl-L-tyrosine may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • N-Formyl tyrosine
CAS numberNot Available
WeightAverage: 209.1986
Monoisotopic: 209.068807845
InChI KeyROUWPHMRHBMAFE-VIFPVBQESA-N
InChIInChI=1S/C10H11NO4/c12-6-11-9(10(14)15)5-7-1-3-8(13)4-2-7/h1-4,6,9,13H,5H2,(H,11,12)(H,14,15)/t9-/m0/s1
IUPAC Name(2S)-3-(4-hydroxyphenyl)-2-formamidopropanoic acid
Traditional IUPAC NameN-formyl-L-tyrosine
Chemical FormulaC10H11NO4
SMILES[H]C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-formyl-alpha-amino acid
  • N-formyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.15 g/LALOGPS
logP0.69ALOGPS
logP0.54ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.05 m³·mol⁻¹ChemAxon
Polarizability19.97 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
L-Tyrosine + N10-Formyl-THFN-Formyl-L-tyrosine + 5,6,7,8-Tetrahydrofolic acid + hydron
N-Formyl-L-tyrosine + NADPH + hydronN,N'-Diformyldityrosine + NADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Briza, P., Kalchhauser, H., Pittenauer, E., Allmaier, G., Breitenbach, M. (1996). "N,N'-Bisformyl dityrosine is an in vivo precursor of the yeast ascospore wall." Eur J Biochem 239:124-131.8706696
  • Melo, N. R., Moran, G. P., Warrilow, A. G., Dudley, E., Smith, S. N., Sullivan, D. J., Lamb, D. C., Kelly, D. E., Coleman, D. C., Kelly, S. L. (2008). "CYP56 (Dit2p) in Candida albicans: characterization and investigation of its role in growth and antifungal drug susceptibility." Antimicrob Agents Chemother 52:3718-3724.18663031
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID50603
HMDB IDNot Available
Pubchem Compound ID13025455
Kegg IDNot Available
ChemSpider ID18525997
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Involved in spore wall maturation. Catalyzes a two step reaction that leads to the LL-dityrosine containing precursor of the spore wall
Gene Name:
DIT1
Uniprot ID:
P21623
Molecular weight:
61390.10156
Reactions
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5
Gene Name:
NCP1
Uniprot ID:
P16603
Molecular weight:
76771.10156
Reactions
NADPH + n oxidized hemoprotein → NADP(+) + n reduced hemoprotein.