MiMeDB: Showing metabocard for N-Acetyl-D-tyrosine (MMDBc0033202)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:38:52 UTC

Update Date

2025-10-07 16:07:57 UTC

Metabolite ID

MMDBc0033202

Metabolite Identification

Common Name

N-Acetyl-D-tyrosine

Description

N-Acetyl-D-tyrosine is a member of the amino acid derivative chemical class, specifically classified as an N-acetylated form of the amino acid D-tyrosine. Its chemical structure features an acetyl group attached to the nitrogen atom of the amino group of D-tyrosine, which alters its solubility and reactivity compared to its parent amino acid. In biochemical pathways, N-acetyl-D-tyrosine is involved in various metabolic processes, including those related to protein synthesis and neurotransmitter regulation. It can serve as a substrate for various enzymes, where kinetic parameters such as Michaelis constants (K m) and maximum reaction velocities (V max) have been assessed in studies involving multiple N-acetylated amino acids, including N-acetyl-D-tyrosine itself (PMID:29509381 ). This highlights its relevance in enzymatic reactions and its potential role in metabolic pathways that utilize N-acetylated amino acids for various physiological functions.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222502D          

 16 16  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033202

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m1/s1

> <INCHI_KEY>
CAHKINHBCWCHCF-SNVBAGLBSA-N

> <FORMULA>
C11H13NO4

> <MOLECULAR_WEIGHT>
223.2252

> <EXACT_MASS>
223.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.840450006223936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.5928963343333332

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.504642405547322

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6702360614092835

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4776622716829717

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
56.54100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Not Available

Molecular Formula

C₁₁H₁₃NO₄

Average Mass

223.2252

Monoisotopic Mass

223.084457909

IUPAC Name

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

Traditional Name

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

CAS Registry Number

19764-32-0

SMILES

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

InChI Identifier

InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m1/s1

InChI Key

CAHKINHBCWCHCF-SNVBAGLBSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	1.03	ALOGPS
logP	0.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-1.5	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	56.54 m³·mol⁻¹	ChemAxon
Polarizability	21.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-052f-9810000000-1b2e358b53063de15d83	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05gi-0960000000-521b33c688de6d5af3c6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0540-0910000000-11b06e8237181862ad09	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4900000000-0ed4f6b83b0e699609da	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1690000000-1c3495d31ad780bf247c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ir-4920000000-04fd94657e89950888ef	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-a5cd6e5756fee449095e	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	299.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	103.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	315.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	316.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	314.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	248.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1237.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	227.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	477.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	184.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	223.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	160.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	102.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	156.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	411.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	81.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	223.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1030.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	707.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_1	CC(=O)N[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	standard non polar	2025-10-24	2281.22
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_2	CC(=O)N[C@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2481.86
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_3	CC(=O)N([C@H](CC1=CC=C(O)C=C1)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2418.96
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_4	CC(=O)N[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1711.42
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_5	CC(=O)N([C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2248.78
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_6	CC(=O)N([C@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2385.64
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_7	CC(=O)N([C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1763.87
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_1	CC(=O)N[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	standard polar	2025-10-24	1685.62
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_2	CC(=O)N[C@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2391.86
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_3	CC(=O)N([C@H](CC1=CC=C(O)C=C1)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1388.3
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_4	CC(=O)N[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1640.76
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_5	CC(=O)N([C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1495.93
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_6	CC(=O)N([C@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2155.78
Gas Chromatography	N-Acetyl-D-tyrosine_TMS_7	CC(=O)N([C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1714.91

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0026119	D-Tyrosine	N-Acetyl-D-tyrosine	D-amino-acid N-acetyltransferase HPA3	Acetylation	RHEA	34755880

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

853750

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Yow GY, Uo T, Yoshimura T, Esaki N: D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids. Arch Microbiol. 2004 Nov;182(5):396-403. doi: 10.1007/s00203-004-0724-y. [PubMed:15375647 ]
Yow GY, Uo T, Yoshimura T, Esaki N: Physiological role of D-amino acid-N-acetyltransferase of Saccharomyces cerevisiae: detoxification of D-amino acids. Arch Microbiol. 2006 Mar;185(1):39-46. doi: 10.1007/s00203-005-0060-x. Epub 2005 Dec 14. [PubMed:16362288 ]
Scheer M, Grote A, Chang A, Schomburg I, Munaretto C, Rother M, Sohngen C, Stelzer M, Thiele J, Schomburg D: BRENDA, the enzyme information system in 2011. Nucleic Acids Res. 2011 Jan;39(Database issue):D670-6. doi: 10.1093/nar/gkq1089. Epub 2010 Nov 9. [PubMed:21062828 ]

Showing metabocard for N-Acetyl-D-tyrosine (MMDBc0033202)

MOL for #<Metabolite:0x00007f9ab6a486e0>

3D MOL for #<Metabolite:0x00007f9ab6a486e0>

3D SDF for #<Metabolite:0x00007f9ab6a486e0>

3D-SDF for #<Metabolite:0x00007f9ab6a486e0>

PDB for #<Metabolite:0x00007f9ab6a486e0>

3D PDB for #<Metabolite:0x00007f9ab6a486e0>

SMILES for #<Metabolite:0x00007f9ab6a486e0>

INCHI for #<Metabolite:0x00007f9ab6a486e0>

Structure for #<Metabolite:0x00007f9ab6a486e0>

3D Structure for #<Metabolite:0x00007f9ab6a486e0>