MiMeDB: Showing metabocard for D-Tyrosine (MMDBc0030387)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:06:20 UTC

Update Date

2024-10-11 02:53:33 UTC

Metabolite ID

MMDBc0030387

Metabolite Identification

Common Name

D-Tyrosine

Description

D-Tyrosine is one of the two enantiomers of tyrosine. Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 22 amino acids that are used by cells to synthesize proteins. Its codons are UAC and UAU. It is a non-essential amino acid with a polar side group. (Wikipedia ) L-Tyrosine is the correct tyrosine isomer used in building proteins, and aminoacyl-tRNA synthetases ensure the exclusion of D-amino acids like D-tyrosine from translation. But sometimes, tyrosyl-tRNA synthetases use D-tyrosine by mistake. Hence, D-tyrosine can be toxic to E. coli, especially in absence of D-Tyr-tRNATyr deacylase to remove the incorrectly-made tRNAs containing D-tyrosine. (PMID 15292242 )

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303202019012D          

 13 13  0  0  1  0            999 V2000
    1.8098    1.4608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8098    0.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243    0.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953    0.2233    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0953   -0.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809    0.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3336    0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3336   -0.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481    0.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625    0.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481   -1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625   -0.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4770   -1.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030387

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
OUYCCCASQSFEME-MRVPVSSYSA-N

> <FORMULA>
C9H11NO3

> <MOLECULAR_WEIGHT>
181.1885

> <EXACT_MASS>
181.073893223

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.05508871589717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-1.4885940366836234

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.792157836784154

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9998472511533611

> <JCHEM_PKA_STRONGEST_BASIC>
9.185299922384795

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
47.09720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(.+-.)-tyrosine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       3.378   2.727   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.378   1.187   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.712   0.417   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.045   0.417   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.045  -1.123   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.711   1.187   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.623   0.417   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.623  -1.123   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.956   1.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.290   0.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.956  -1.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.290  -1.123   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.624  -1.893   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    7   10                                                       
CONECT   10    9   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
(2R)-2-Amino-3-(4-hydroxyphenyl)propanoic acid	ChEBI
(R)-2-Amino-3-(p-hydroxyphenyl)propionic acid	ChEBI
(R)-3-(p-Hydroxyphenyl)alanine	ChEBI
D-Tyr	ChEBI
D-Tyrosin	ChEBI
DTY	ChEBI
(2R)-2-Amino-3-(4-hydroxyphenyl)propanoate	Generator
(R)-2-Amino-3-(p-hydroxyphenyl)propionate	Generator

Molecular Formula

C₉H₁₁NO₃

Average Mass

181.1885

Monoisotopic Mass

181.073893223

IUPAC Name

(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

(.+-.)-tyrosine

CAS Registry Number

556-02-5

SMILES

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

InChI Identifier

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

InChI Key

OUYCCCASQSFEME-MRVPVSSYSA-N

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
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
D-alpha-amino acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:28479 )
tyrosine (CHEBI:28479 )
Other amino acids (C06420 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.67 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	83.55 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.1 m³·mol⁻¹	ChemAxon
Polarizability	18.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-4900000000-9be1412408207db5df4e	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q0-0900000000-64b5df3e494e5df5c1be	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-c38735d64e2a16bd0c68	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-6900000000-6696908ff67c37922f99	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-941af648c85b3f0f7c66	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-1900000000-b7d3075f2496303aeb37	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9700000000-c242deae91617b5e8735	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, D₂O, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Archaea/Archaea	Euryarchaeota	1
Bacteria	Firmicutes	1	Human feces
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB03839

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06420

BioCyc ID

D-TYROSINE

BiGG ID

Not Available

Wikipedia Link

Tyrosine

METLIN ID

Not Available

PubChem Compound

71098

PDB ID

Not Available

ChEBI ID

28479

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for D-Tyrosine (MMDBc0030387)

MOL for #<Metabolite:0x00007fdb70b80030>

3D MOL for #<Metabolite:0x00007fdb70b80030>

3D SDF for #<Metabolite:0x00007fdb70b80030>

3D-SDF for #<Metabolite:0x00007fdb70b80030>

PDB for #<Metabolite:0x00007fdb70b80030>

3D PDB for #<Metabolite:0x00007fdb70b80030>

SMILES for #<Metabolite:0x00007fdb70b80030>

INCHI for #<Metabolite:0x00007fdb70b80030>

Structure for #<Metabolite:0x00007fdb70b80030>

3D Structure for #<Metabolite:0x00007fdb70b80030>