N-Formyl-L-tyrosine (YMDB00726)

Identification

YMDB ID

YMDB00726

Name

N-Formyl-L-tyrosine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-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

MOL SDF PDB SMILES InChI

Synonyms

N-Formyl tyrosine

CAS number

Not Available

Weight

Average: 209.1986
Monoisotopic: 209.068807845

InChI Key

ROUWPHMRHBMAFE-VIFPVBQESA-N

InChI

InChI=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 Name

N-formyl-L-tyrosine

Chemical Formula

C₁₀H₁₁NO₄

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

L-tyrosine derivative (CHEBI:50603 )
N-formyl amino acid (CHEBI:50603 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.15 g/L	ALOGPS
logP	0.69	ALOGPS
logP	0.54	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.05 m³·mol⁻¹	ChemAxon
Polarizability	19.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

L-Tyrosine + N10-Formyl-THF → N-Formyl-L-tyrosine + 5,6,7,8-Tetrahydrofolic acid + hydron

N-Formyl-L-tyrosine + NADPH + hydron → N,N'-Diformyldityrosine + NADP

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btc-5900000000-e521d2098c5abdef9981	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0920000000-f08d99e117000af3e5be	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0900000000-0f16e7082e4c0c10d4ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-285000893be1c14b03f1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-7890000000-b265617a7e4171329051	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-6910000000-2dbea69b00e84e657da0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9100000000-831d5fc8fec62f4520b2	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	50603
HMDB ID	Not Available
Pubchem Compound ID	13025455
Kegg ID	Not Available
ChemSpider ID	18525997
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Spore wall maturation protein DIT1

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

Protein Details

2. NADPH--cytochrome P450 reductase

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.

Structure for #<Compound:0xac195bd4>

Enzymes

Reactions

Reactions