Molecule

D-tyrosinium

AlkaPlorer ID: AK003610

Synonym: '', 'D-Tyrosine', '(1R)-1-carboxy-2-(4-hydroxyphenyl)ethanaminium', '(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid', '(R)-3-(p-Hydroxyphenyl)alanine', '(R)-2-Amino-3-(p-hydroxyphenyl)propionic acid', 'D-tyrosine', '(S)-2-Amino-3-(p-hydroxyphenyl)propionic acid', 'DTY', '60-18-4', '3-(p-Hydroxyphenyl)alanine', '2-amino-3-(4-hydroxyphenyl)propanoic acid', '2-Amino-3-(p-hydroxyphenyl)propionic acid', '(2R)-2-amino-3-(4-hydroxyphenyl)propanoate', 'L-Tyrosin', '(-)-alpha-amino-p-hydroxyhydrocinnamic acid', 'TYROSINE', 'Y', '16978-66-8', '(S)-3-(p-Hydroxyphenyl)alanine', 'D-tyrosine cation', 'D-TYROSINE', 'D-tyrosine dianion', '4-hydroxy-L-phenylalanine', 'Tyrosine', 'D-tyrosine monoanion', 'L-Tyr', 'tirosina', 'Tyr', '(S)-(-)-Tyrosine', 'D-tyrosinate(1-)', 'D-Tyrosin', 'D-tyrosinate(2-)', '(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid', 'L-Tyrosine', 'Tyrosin', 'D-Tyr', 'L-tyrosine', 'tyrosine', '(S)-alpha-amino-4-hydroxybenzenepropanoic acid', '(2R)-2-amino-3-(4-oxidophenyl)propanoate', '(S)-Tyrosine'

IUPAC Name: (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid

Structure

SMILES: N[C@H](CC1=CC=C(O)C=C1)C(=O)O

InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1

InChIKey: OUYCCCASQSFEME-MRVPVSSYSA-N

Reference

Formation of d-Tyrosyl-tRNATyr Accounts for the Toxicity of d-Tyrosine toward Escherichia coli

PubChem CID: 71098

CAS: 556-02-5

LOTUS: LTS0232701

SuperNatural Ⅲ: SN0275914-01

NPASS: NPC322005

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Ginkgo biloba	Ginkgo	Ginkgoaceae	Ginkgoales	Ginkgoopsida	Streptophyta	Viridiplantae	Eukaryota
Sinapis alba	Sinapis	Brassicaceae	Brassicales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Selaginella pulvinata	Selaginella	Selaginellaceae	Selaginellales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Calvatia gigantea	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Brassica juncea	Brassica	Brassicaceae	Brassicales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Allium sativum	Allium	Amaryllidaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Calvatia fenzlii	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Calvatia lilacina	Calvatia	Lycoperdaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Ganoderma sinense	Ganoderma	Polyporaceae	Polyporales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Selaginella tamariscina	Selaginella	Selaginellaceae	Selaginellales	Lycopodiopsida	Streptophyta	Viridiplantae	Eukaryota
Ganoderma lucidum	Ganoderma	Polyporaceae	Polyporales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Escherichia coli	Escherichia	Enterobacteriaceae	Enterobacterales	Gammaproteobacteria	Pseudomonadota	None	Bacteria
Pinellia ternata	Pinellia	Araceae	Alismatales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 181.191

TPSA？: 83.55

MolLogP？: 0.3466

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Candida glabrata CBS 138	Carbonic anhydrase	Ka	7.1	uM	10.1016/j.bmcl.2010.01.054
Homo sapiens	Carbonic anhydrase I	KA	0.04	uM	10.1016/j.bmc.2018.07.011
Homo sapiens	Carbonic anhydrase I	KA	0.34	uM	10.1016/j.bmcl.2012.08.088
Homo sapiens	Carbonic anhydrase I	KA	0.34	uM	10.1016/j.bmcl.2012.12.009
Homo sapiens	Carbonic anhydrase I	KA	nan	None	10.1016/j.bmcl.2016.11.027
Homo sapiens	Carbonic anhydrase II	Ka	0.058	uM	10.1016/j.bmcl.2010.01.054
Homo sapiens	Carbonic anhydrase II	KA	0.013	uM	10.1016/j.bmc.2018.07.011
Homo sapiens	Carbonic anhydrase II	KA	0.087	uM	10.1016/j.bmcl.2012.08.088
Homo sapiens	Carbonic anhydrase II	KA	0.087	uM	10.1016/j.bmcl.2012.12.009
Homo sapiens	Carbonic anhydrase II	KA	nan	None	10.1016/j.bmcl.2016.11.027
Homo sapiens	L-type amino acid transporter 1	Activity	85.0	%	10.1021/acs.jmedchem.8b01007
Homo sapiens	L-type amino acid transporter 1	IC50	380000.0	nM	10.1021/acs.jmedchem.8b01007
Homo sapiens	L-type amino acid transporter 1	Inhibition	35.0	%	10.1021/acs.jmedchem.8b01007
Homo sapiens	Menin/Histone-lysine N-methyltransferase MLL	Potency	39810.7	nM	None
Homo sapiens	Regulator of G-protein signaling 4	Potency	75.2	nM	None
Methanobacterium thermoautotrophicum	Carbonic anhydrase	Ka	19.2	uM	10.1016/j.bmcl.2010.01.054
Methanosarcina thermophila	Carbonic anhydrase	KA	nan	None	10.1016/j.bmcl.2016.11.027
Rattus norvegicus	Monocarboxylate transporter 10	Activity	nan	None	10.1074/jbc.m009462200
Saccharomyces cerevisiae S288c	Carbonic anhydrase	Ka	84.0	uM	10.1016/j.bmcl.2010.01.054
Staphylococcus aureus	Staphylococcus aureus	Activity	85.0	%	10.1016/j.bmcl.2021.128259
Staphylococcus aureus	Staphylococcus aureus	Activity	119.0	%	10.1016/j.bmcl.2021.128259
Staphylococcus aureus	Staphylococcus aureus	Inhibition	70.0	%	10.1016/j.bmcl.2021.128259
Trypanosoma cruzi (strain CL Brener)	Carbonic anhydrase-like protein, putative	KA	2.8	uM	10.1016/j.bmc.2018.07.011
None	Unchecked	KA	0.11	uM	10.1016/j.bmcl.2012.12.009
None	Unchecked	KA	0.83	uM	10.1016/j.bmcl.2012.08.088
None	Unchecked	KA	0.83	uM	10.1016/j.bmcl.2012.12.009
None	Unchecked	KA	1.27	uM	10.1016/j.bmc.2018.07.011
None	Unchecked	KA	25.1	uM	10.1016/j.bmcl.2016.01.078
None	Unchecked	KA	32.8	uM	10.1016/j.bmcl.2016.11.027
None	Unchecked	Kcat	5.8	10'5/s	10.1016/j.bmcl.2016.11.027

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000859	OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@H](Cc1ccc(O)cc1)C(=O)O>>OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)[C@H](N)Cc2ccc(O)cc2)[C@@H]1O	MNXR186616
AKRT000873	*OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)[C@H](O)[C@@H]1OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](OC(=O)[C@H](N)Cc2ccc(O)cc2)[C@@H]1O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	RXN-19727
AKRT002329	CC(=O)NC(Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_77908
AKRT003093	CC(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O>>CC(=O)O.N[C@H](Cc1ccc(O)cc1)C(=O)O	None
AKRT003094	CC(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_77901
AKRT004090	CC(=O)O.N[C@H](Cc1ccc(O)cc1)C(=O)O>>CC(=O)NC(Cc1ccc(O)cc1)C(=O)O	enzymemap_77908
AKRT004714	CC(=O)[CoA].N[C@H](Cc1ccc(O)cc1)C(=O)O>>CC(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_30762
AKRT005252	CC(C)=CCOP(=O)(O)OP(=O)(O)O.N[C@H](Cc1ccc(O)cc1)C(=O)O>>CC(C)=CCOc1ccc(C[C@@H](N)C(=O)O)cc1	enzymemap_39948
AKRT005953	CC(C)C[C@H](NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_67784
AKRT009737	CCOC(=O)[C@H](N)Cc1ccc(O)cc1>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_51112
AKRT010976	CO.N[C@H](Cc1ccc(O)cc1)C(=O)O>>COC(=O)[C@H](N)Cc1ccc(O)cc1	enzymemap_52991
AKRT011127	COC(=O)[C@H](N)Cc1ccc(O)cc1>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_52991
AKRT011989	CP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O.N[C@H](Cc1ccc(O)cc1)C(=O)O>>CP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OC(=O)[C@H](N)Cc1ccc(O)cc1	57448
AKRT012657	C[33S].N[C@H](Cc1ccc(O)cc1)C(=O)O>>Cc1cc(C[C@@H](N)C(=O)O)ccc1O	None
AKRT012724	C[C@@H](N)C(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_67348
AKRT014691	C[SAH].N[C@H](Cc1ccc(O)cc1)C(=O)O>>Cc1cc(C[C@@H](N)C(=O)O)ccc1O	enzymemap_26930
AKRT015324	Cc1ncc(COP(=O)(O)O)c(C=O)c1O.N[C@H](Cc1ccc(O)cc1)C(=O)O>>Cc1ncc(COP(=O)(O)O)c(CN[C@H](Cc2ccc(O)cc2)C(=O)O)c1O	enzymemap_22610
AKRT015365	Cc1ncc(COP(=O)(O)O)c(CN[C@H](Cc2ccc(O)cc2)C(=O)O)c1O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_22591
AKRT016309	N=C(O)[C@H](N)Cc1ccc(O)cc1>>N[C@H](Cc1ccc(O)cc1)C(=O)O	MNXR131569
AKRT017131	NC(=O)N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_77865
AKRT019982	N[C@@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)O	59808
AKRT020352	N[C@H](Cc1ccc(O)cc1)C(=O)O.O=C(O)CCC(=O)C(=O)O>>N[C@H](CCC(=O)O)C(=O)O.O=C(O)C(=O)Cc1ccc(O)cc1	None
AKRT020353	N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@@H](C=O)Cc1ccc(O)cc1	enzymemap_16670
AKRT020354	N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@@H](Cc1ccc(O)cc1)C(=O)O	None
AKRT020355	N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(O)cc1)C(=O)OS(=O)(=O)O	enzymemap_50007
AKRT020356	N[C@H](Cc1ccc(O)cc1)C(=O)O>>N[C@H](Cc1ccc(OS(=O)(=O)O)cc1)C(=O)O	enzymemap_50007
AKRT020357	N[C@H](Cc1ccc(O)cc1)C(=O)O>>O=C(O)C(=O)Cc1ccc(O)cc1	70959
AKRT022609	O=C(O)C(=O)Cc1ccc(O)cc1>>N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_22468
AKRT023417	O=C([CoA])/C=C/c1ccc(O)c(O)c1.N[C@H](Cc1ccc(O)cc1)C(=O)O>>O=C(/C=C/c1ccc(O)c(O)c1)N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_28816
AKRT023428	O=C([CoA])/C=C/c1ccc(O)cc1.N[C@H](Cc1ccc(O)cc1)C(=O)O>>O=C(/C=C/c1ccc(O)cc1)N[C@H](Cc1ccc(O)cc1)C(=O)O	enzymemap_28814