MiMeDB: Showing metabocard for 4-O-dimethylallyl-L-tyrosine (MMDBc0055533)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:58:15 UTC

Update Date

2022-08-12 20:09:24 UTC

Metabolite ID

MMDBc0055533

Metabolite Identification

Common Name

4-O-dimethylallyl-L-tyrosine

Description

O-prenyltyrosine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on O-prenyltyrosine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221582D          

 19 19  0  0  1  0            999 V2000
    0.7145    4.5375    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 13 15  1  1  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18  8  1  0  0  0  0
 18 12  1  0  0  0  0
 13 19  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055533

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO3/c1-10(2)7-8-18-12-5-3-11(4-6-12)9-13(15)14(16)17/h3-7,13H,8-9,15H2,1-2H3,(H,16,17)/t13-/m0/s1

> <INCHI_KEY>
DVPQPQUTSYCKEZ-ZDUSSCGKSA-N

> <FORMULA>
C14H19NO3

> <MOLECULAR_WEIGHT>
249.31

> <EXACT_MASS>
249.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.690706686237878

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-amino-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoic acid

> <JCHEM_LOGP>
0.018674290714961492

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9821850337376814

> <JCHEM_PKA_STRONGEST_BASIC>
9.46992834725094

> <JCHEM_POLAR_SURFACE_AREA>
72.55

> <JCHEM_REFRACTIVITY>
70.69770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334   8.470   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  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   11                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7    8   10                                                       
CONECT    8    7   18                                                       
CONECT    9   11   13                                                       
CONECT   10    1    2    7                                                  
CONECT   11    3    4    9                                                  
CONECT   12    5    6   18                                                  
CONECT   13    9   14   15   19                                             
CONECT   14   13   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    8   12                                                       
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

Synonyms

Value	Source
4-O-Dimethylallyl-L-tyrosine	ChEBI
4-O-Prenyl-L-tyrosine zwitterion	ChEBI

Molecular Formula

C₁₄H₁₉NO₃

Average Mass

249.31

Monoisotopic Mass

249.136493476

IUPAC Name

(2S)-2-amino-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoic acid

Traditional Name

(2S)-2-amino-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H19NO3/c1-10(2)7-8-18-12-5-3-11(4-6-12)9-13(15)14(16)17/h3-7,13H,8-9,15H2,1-2H3,(H,16,17)/t13-/m0/s1

InChI Key

DVPQPQUTSYCKEZ-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
L-alpha-amino acid
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Carboxylic acid salt
Amino acid
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic salt
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Hydrocarbon derivative
Primary amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

L-tyrosine derivative (CHEBI:79185 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.019	ChemAxon
pKa (Strongest Acidic)	1.98	ChemAxon
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.7 m³·mol⁻¹	ChemAxon
Polarizability	27.69 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 (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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
Eukaryota/Fungi	Ascomycota	2	Human feces

Exposure Sources

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

31150533

KEGG Compound ID

Not Available

BioCyc ID

CPD-16653

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68360929

PDB ID

Not Available

ChEBI ID

78314

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 4-O-dimethylallyl-L-tyrosine (MMDBc0055533)

MOL for #<Metabolite:0x00007fdb38674fb0>

3D MOL for #<Metabolite:0x00007fdb38674fb0>

3D SDF for #<Metabolite:0x00007fdb38674fb0>

3D-SDF for #<Metabolite:0x00007fdb38674fb0>

PDB for #<Metabolite:0x00007fdb38674fb0>

3D PDB for #<Metabolite:0x00007fdb38674fb0>

SMILES for #<Metabolite:0x00007fdb38674fb0>

INCHI for #<Metabolite:0x00007fdb38674fb0>

Structure for #<Metabolite:0x00007fdb38674fb0>

3D Structure for #<Metabolite:0x00007fdb38674fb0>