N,N'-Diformyldityrosine (YMDB00739)

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Identification

YMDB ID

YMDB00739

Name

N,N'-Diformyldityrosine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N,N'-Diformyldityrosine 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,N'-Diformyldityrosine is an extremely weak basic (essentially neutral) compound (based on its pKa). N,N'-Diformyldityrosine may be a unique S. cerevisiae (yeast) metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

N,N'-bisformyl dityrosine
N,N'-bisformyldityrosine

CAS number

Not Available

Weight

Average: 416.3814
Monoisotopic: 416.121965626

InChI Key

OUNKRBSXIMLJRR-UHFFFAOYSA-N

InChI

InChI=1S/C20H20N2O8/c23-9-21-15(19(27)28)7-11-1-3-17(25)13(5-11)14-6-12(2-4-18(14)26)8-16(20(29)30)22-10-24/h1-6,9-10,15-16,25-26H,7-8H2,(H,21,23)(H,22,24)(H,27,28)(H,29,30)

IUPAC Name

3-{3-[5-(2-carboxy-2-formamidoethyl)-2-hydroxyphenyl]-4-hydroxyphenyl}-2-formamidopropanoic acid

Traditional IUPAC Name

N,N'-bisformyl dityrosine

Chemical Formula

C₂₀H₂₀N₂O₈

SMILES

[H]C(=O)NC(CC1=CC(=C(O)C=C1)C1=C(O)C=CC(CC(NC([H])=O)C(O)=O)=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
Biphenyl
N-formyl-alpha-amino acid
N-formyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:50611 )
N-formyl amino acid (CHEBI:50611 )

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	0.16 g/L	ALOGPS
logP	0.88	ALOGPS
logP	0.76	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.26 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	103.18 m³·mol⁻¹	ChemAxon
Polarizability	40.47 Å³	ChemAxon
Number of Rings	2	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

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

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 (TMS_4_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009200000-c294579eaeae3691fa53	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-009g-0019000000-13747298c320ab44eb09	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0097000000-082d55704ad5cdf3f17d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-7206900000-a37906e3b3e9c85b322b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0096-9418200000-723d6f74ffff4a86281c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9000000000-cb6fc4d7f3b8da959021	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	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
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

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	50611
HMDB ID	Not Available
Pubchem Compound ID	14554236
Kegg ID	Not Available
ChemSpider ID	21865768
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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.

Transporters

Protein Details

1. Uncharacterized transporter YBR180W

General function:: Involved in transmembrane transport
Specific function:: Not Available
Gene Name:: Not Available
Uniprot ID:: P38125
Molecular weight:: 63406.19922

Structure for #<Compound:0xac052f10>

Enzymes

Reactions

Transporters