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Showing metabocard for Tyrosol (HMDB0004284)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 16:05:03 UTC
Update Date2023-02-21 17:16:59 UTC
HMDB IDHMDB0004284
Secondary Accession Numbers
  • HMDB04284
Metabolite Identification
Common NameTyrosol
DescriptionTyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375 ). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004284 (Tyrosol)

  Mrv1652304272018112D          

 10 10  0  0  0  0            999 V2000
   -1.0154    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298    0.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444    0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7299   -0.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -0.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for HMDB0004284 (Tyrosol)

HMDB0004284
     RDKit          3D
Tyrosol
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.6008    1.3348   -0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919    0.0174   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -0.8370    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385   -0.4005    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    0.5171    1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941    0.8980    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3859    0.3689   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7135    0.7832   -0.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8775   -0.5492   -1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.9263   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.9174   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.3908   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -0.1487   -1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -0.9321    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -1.8602   -0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.9603    1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255    1.6099    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3908    0.2343    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -0.9472   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -1.6492   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
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3D SDF for HMDB0004284 (Tyrosol)

  Mrv1652304272018112D          

 10 10  0  0  0  0            999 V2000
   -1.0154    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298    0.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444    0.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4444   -0.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7299   -0.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154   -0.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -0.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3009    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4135    0.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004284

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2

> <INCHI_KEY>
YCCILVSKPBXVIP-UHFFFAOYSA-N

> <FORMULA>
C8H10O2

> <MOLECULAR_WEIGHT>
138.1638

> <EXACT_MASS>
138.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.852126354348522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-hydroxyethyl)phenol

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.1909919319999998

> <ALOGPS_LOGS>
-0.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.974912510505817

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.20403264247904

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4009234189336803

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
39.60980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tyrosol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0004284 (Tyrosol)

HMDB0004284
     RDKit          3D
Tyrosol
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.6008    1.3348   -0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919    0.0174   -0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384   -0.8370    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385   -0.4005    0.1483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    0.5171    1.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5941    0.8980    0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3859    0.3689   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7135    0.7832   -0.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8775   -0.5492   -1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5463   -0.9263   -0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955    1.9174   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.3908   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -0.1487   -1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -0.9321    1.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -1.8602   -0.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.9603    1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0255    1.6099    1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3908    0.2343    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060   -0.9472   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -1.6492   -1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
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PDB for HMDB0004284 (Tyrosol)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.895   0.624   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.229   1.394   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.563   0.624   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.563  -0.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.229  -1.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.895  -0.916   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.897  -1.686   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.562   1.394   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.772   0.624   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.105   1.394   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0004284 (Tyrosol)

COMPND    HMDB0004284
HETATM    1  O1  UNL     1       2.601   1.335  -0.171  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.592   0.017  -0.544  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.638  -0.837   0.255  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.238  -0.400   0.148  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.275   0.517   1.041  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.594   0.898   0.903  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.386   0.369  -0.113  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.713   0.783  -0.214  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.877  -0.549  -1.008  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.546  -0.926  -0.860  1.00  0.00           C  
HETATM   11  H1  UNL     1       2.396   1.917  -0.967  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.620  -0.391  -0.328  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.437  -0.149  -1.624  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.970  -0.932   1.315  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.715  -1.860  -0.171  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.291   0.960   1.847  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.025   1.610   1.580  1.00  0.00           H  
HETATM   18  H8  UNL     1      -4.391   0.234   0.307  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.506  -0.947  -1.787  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.184  -1.649  -1.583  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    5   10
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   18
CONECT    9   10   10   19
CONECT   10   20
END
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SMILES for HMDB0004284 (Tyrosol)

OCCC1=CC=C(O)C=C1
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INCHI for HMDB0004284 (Tyrosol)

InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H10O2
Average Molecular Weight138.1638
Monoisotopic Molecular Weight138.068079564
IUPAC Name4-(2-hydroxyethyl)phenol
Traditional Nametyrosol
CAS Registry Number501-94-0
SMILES
OCCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
InChI KeyYCCILVSKPBXVIP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosols. These are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassTyrosols and derivatives
Direct ParentTyrosols
Alternative Parents
Substituents
  • Tyrosol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point308.00 to 311.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility123800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.851 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker138.70830932474
[M-H]-Not Available138.708http://allccs.zhulab.cn/database/detail?ID=AllCCS00001919
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID673
FooDB IDFDB012695
KNApSAcK IDC00029515
Chemspider ID9964
KEGG Compound IDC06044
BioCyc IDCPD3O-4151
BiGG IDNot Available
Wikipedia LinkTyrosol
METLIN ID7044
PubChem Compound10393
PDB IDNot Available
ChEBI ID1879
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1203831
References
Synthesis ReferenceZheng, Hong; Gao, Wenfang; Ji, Xueshi; Zhang, Shoufang. Improved method for synthesis of Tyrosol. Zhongguo Yaowu Huaxue Zazhi (2002), 12(3), 166-167.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Quiles JL, Farquharson AJ, Simpson DK, Grant I, Wahle KW: Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells. Br J Nutr. 2002 Sep;88(3):225-34; discussion 223-4. [PubMed:12207832 ]
  2. Vissers MN, Zock PL, Roodenburg AJ, Leenen R, Katan MB: Olive oil phenols are absorbed in humans. J Nutr. 2002 Mar;132(3):409-17. [PubMed:11880564 ]
  3. Tsarbopoulos A, Gikas E, Papadopoulos N, Aligiannis N, Kafatos A: Simultaneous determination of oleuropein and its metabolites in plasma by high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):157-64. [PubMed:12535848 ]
  4. Miles EA, Zoubouli P, Calder PC: Differential anti-inflammatory effects of phenolic compounds from extra virgin olive oil identified in human whole blood cultures. Nutrition. 2005 Mar;21(3):389-94. [PubMed:15797683 ]
  5. Visioli F, Galli C, Bornet F, Mattei A, Patelli R, Galli G, Caruso D: Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000 Feb 25;468(2-3):159-60. [PubMed:10692578 ]
  6. Covas MI, Miro-Casas E, Fito M, Farre-Albadalejo M, Gimeno E, Marrugat J, De La Torre R: Bioavailability of tyrosol, an antioxidant phenolic compound present in wine and olive oil, in humans. Drugs Exp Clin Res. 2003;29(5-6):203-6. [PubMed:15134375 ]
  7. Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]

Enzymes

Enzyme Details
1. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Tyrosol → Tyrosol 4-sulfatedetails