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Showing metabocard for 4-Coumaryl alcohol (HMDB0003654)

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enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 02:37:06 UTC
Update Date2023-02-21 17:16:46 UTC
HMDB IDHMDB0003654
Secondary Accession Numbers
  • HMDB03654
Metabolite Identification
Common Name4-Coumaryl alcohol
Description4-Coumaryl alcohol (CAS: 3690-05-9), also known as p-coumaryl alcohol or 4-hydroxycoumarin, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. Outside of the human body, 4-Coumaryl alcohol has been detected, but not quantified in, several different foods, such as loquats, sweet basils, capers, red algae, and squashberries. This could make 4-coumaryl alcohol a potential biomarker for the consumption of these foods. 4-Coumaryl alcohol is a substrate for NAD(P)H dehydrogenase 1.
Structure
Data?1676999806
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003654 (4-Coumaryl alcohol)


  Mrv1652307232017532D          

 11 11  0  0  0  0            999 V2000
   -1.0489    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4779    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    0.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344    2.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089    2.0644    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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for HMDB0003654 (4-Coumaryl alcohol)

HMDB0003654
     RDKit          3D
4-Coumaryl alcohol
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.9626    1.5499    0.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963    0.4196   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0148    0.5405   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794   -0.3480    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -0.3254    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    0.6366   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3137    0.5847   -0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -0.4223   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -0.4905   -0.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632   -1.4088    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -1.3386    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3131    2.1744   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    0.2533   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7237   -0.4474    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    1.3526   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -1.1547    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904    1.4429   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    1.3567   -1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -0.0464    0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -2.2159    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -2.1131    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for HMDB0003654 (4-Coumaryl alcohol)


  Mrv1652307232017532D          

 11 11  0  0  0  0            999 V2000
   -1.0489    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    2.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4778    2.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4779    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634    0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924    0.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3344    2.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0944    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089    2.0644    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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003654

> <DATABASE_NAME>
hmdb

> <SMILES>
OC\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+

> <INCHI_KEY>
PTNLHDGQWUGONS-OWOJBTEDSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.349329356202247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.5122464003333331

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.623603279860344

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.510114196257495

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5262025042442593

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
45.1734

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paracoumaryl alcohol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003654 (4-Coumaryl alcohol)

HMDB0003654
     RDKit          3D
4-Coumaryl alcohol
 21 21  0  0  0  0  0  0  0  0999 V2000
    3.9626    1.5499    0.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963    0.4196   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0148    0.5405   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794   -0.3480    0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -0.3254    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9370    0.6366   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3137    0.5847   -0.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -0.4223   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3897   -0.4905   -0.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632   -1.4088    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -1.3386    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3131    2.1744   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686    0.2533   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7237   -0.4474    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    1.3526   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558   -1.1547    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904    1.4429   -1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203    1.3567   -1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -0.0464    0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -2.2159    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4937   -2.1131    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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PDB for HMDB0003654 (4-Coumaryl alcohol)

HEADER    PROTEIN                                 23-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUL-20         0                                  
HETATM    1  C   UNK     0      -1.958   3.853   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.291   4.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.625   3.853   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.625   2.313   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.292   1.543   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.958   2.313   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.959   1.543   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.624   4.623   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.709   3.853   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.043   4.624   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.377   3.854   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   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0003654 (4-Coumaryl alcohol)

COMPND    HMDB0003654
HETATM    1  O1  UNL     1       3.963   1.550   0.606  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.496   0.420  -0.061  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.015   0.540  -0.294  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.179  -0.348   0.207  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.268  -0.325   0.042  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.937   0.637  -0.662  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.314   0.585  -0.771  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.024  -0.422  -0.179  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.390  -0.491  -0.275  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.363  -1.409   0.541  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.006  -1.339   0.635  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.313   2.174  -0.069  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.969   0.253  -1.025  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.724  -0.447   0.587  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.605   1.353  -0.872  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.656  -1.155   0.789  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.390   1.443  -1.138  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.820   1.357  -1.333  1.00  0.00           H  
HETATM   19  H8  UNL     1      -5.021  -0.046   0.400  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.891  -2.216   1.019  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.494  -2.113   1.199  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3   13   14
CONECT    3    4    4   15
CONECT    4    5   16
CONECT    5    6    6   11
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   10
CONECT    9   19
CONECT   10   11   11   20
CONECT   11   21
END
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SMILES for HMDB0003654 (4-Coumaryl alcohol)

OC\C=C\C1=CC=C(O)C=C1
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INCHI for HMDB0003654 (4-Coumaryl alcohol)

InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(E)-4-Coumaryl alcoholChEBI, HMDB
4-Hydroxycinnamyl alcoholChEBI
p-Coumaryl alcoholChEBI
3-(4-Hydroxyphenyl)-1-propaneHMDB
3-OHPPHMDB
4-CoumarinolHMDB
4-Hydroxy-2H-1-benzopyran-2-oneHMDB
4-Hydroxy-2H-chromen-2-oneHMDB
4-HydroxycoumarinHMDB
4-HydroxycoumarineHMDB
BenzotetronateHMDB
Benzotetronic acidHMDB
Hydroxy coumarinHMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidMeSH, HMDB
trans-HPPAMeSH, HMDB
p-Hydroxycinnamic acidMeSH, HMDB
Para-coumaric acidMeSH, HMDB
4-Coumaric acid, (E)-isomerMeSH, HMDB
4-Hydroxycinnamic acidMeSH, HMDB
p-Coumaric acidMeSH, HMDB
4-Coumaric acidMeSH, HMDB
(E)-4-Coumaroyl alcoholChEBI
(E)-p-Coumaryl alcoholHMDB
3-(p-Hydroxyphenyl)-2-propen-1-olHMDB
4-(3-Hydroxy-1-propen-1-yl)phenolHMDB
4-Coumaryl alcoholHMDB
4-Hydroxycinnamic alcoholHMDB
4-[(1E)-3-Hydroxy-1-propenyl]phenolHMDB
Paracoumaryl alcoholHMDB
p-Coumaric alcoholHMDB
p-Cumaric alcoholHMDB
p-Hydroxycinnamic alcoholHMDB
p-Hydroxycinnamyl alcoholHMDB
trans-p-Coumaryl alcoholHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol
Traditional Nameparacoumaryl alcohol
CAS Registry Number20649-40-5
SMILES
OC\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
InChI KeyPTNLHDGQWUGONS-OWOJBTEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamyl alcohols
Sub ClassNot Available
Direct ParentCinnamyl alcohols
Alternative Parents
Substituents
  • Cinnamyl alcohol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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 effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.97 g/LALOGPS
logP1.55ALOGPS
logP1.51ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.8531661259
DarkChem[M-H]-132.94231661259
DeepCCS[M+H]+134.70130932474
DeepCCS[M-H]-130.87330932474
DeepCCS[M-2H]-168.52430932474
DeepCCS[M+Na]+144.06330932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.532859911
AllCCS[M+NH4]+136.332859911
AllCCS[M+Na]+137.532859911
AllCCS[M-H]-131.932859911
AllCCS[M+Na-2H]-133.232859911
AllCCS[M+HCOO]-134.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.55 minutes32390414
Predicted by Siyang on May 30, 20229.8606 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.18 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid35.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1426.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid316.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid189.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid149.6 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid374.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid349.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)113.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid850.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid323.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid916.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid243.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid300.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate443.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA194.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water60.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Coumaryl alcoholOC\C=C\C1=CC=C(O)C=C12766.9Standard polar33892256
4-Coumaryl alcoholOC\C=C\C1=CC=C(O)C=C11598.2Standard non polar33892256
4-Coumaryl alcoholOC\C=C\C1=CC=C(O)C=C11655.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Coumaryl alcohol,1TMS,isomer #1C[Si](C)(C)OC/C=C/C1=CC=C(O)C=C11739.9Semi standard non polar33892256
4-Coumaryl alcohol,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(/C=C/CO)C=C11652.2Semi standard non polar33892256
4-Coumaryl alcohol,2TMS,isomer #1C[Si](C)(C)OC/C=C/C1=CC=C(O[Si](C)(C)C)C=C11817.4Semi standard non polar33892256
4-Coumaryl alcohol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC/C=C/C1=CC=C(O)C=C11993.9Semi standard non polar33892256
4-Coumaryl alcohol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/CO)C=C11912.4Semi standard non polar33892256
4-Coumaryl alcohol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12289.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l1i-2900000000-35b232588497df392bcc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9360000000-71f6e35237794477c9952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Positive-QTOFsplash10-0f89-0900000000-d0aa38e43ffe69c65dce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Positive-QTOFsplash10-001i-1900000000-f35b26b4169e49f896512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Positive-QTOFsplash10-0a4r-9600000000-feffeb0ec4d7bfd7e4212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Negative-QTOFsplash10-0002-0900000000-aa3fec540eb5ff87fecf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Negative-QTOFsplash10-0002-0900000000-926f68e15b016ddc1bf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Negative-QTOFsplash10-05nf-6900000000-53b966254d033e1958102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Positive-QTOFsplash10-0a59-0900000000-ef3175d0cc2e2c422a132021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Positive-QTOFsplash10-0ae9-4900000000-512eaa23bb6e2ec1bf3b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Positive-QTOFsplash10-004i-9200000000-835e5fb65c2a8f70004b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Negative-QTOFsplash10-014j-0900000000-8d131986ef2454e289192021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Negative-QTOFsplash10-0159-0900000000-c01ea2304d08f2059c072021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Negative-QTOFsplash10-014i-3900000000-6bda1a3cbe19b1fee9f72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030494
KNApSAcK IDC00000613
Chemspider ID4444166
KEGG Compound IDC02646
BioCyc IDCOUMARYL-ALCOHOL
BiGG ID2299830
Wikipedia LinkParacoumaryl_alcohol
METLIN ID6971
PubChem Compound5280535
PDB IDNot Available
ChEBI ID64555
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTakahashi, Yukio; Kato, Keiichi; Kubota, Koichi. One-pot preparation of high-purity 4-hydroxycoumarin. Jpn. Kokai Tokkyo Koho (2005), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Maurer HH, Arlt JW: Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):181-95. [PubMed:9766858 ]
  2. Janssen LH, Van Wilgenburg MT, Wilting J: Human serum albumin as an allosteric two-state protein. Evidence from effects of calcium and warfarin on proton binding behaviour. Biochim Biophys Acta. 1981 Jul 28;669(2):244-50. [PubMed:7284438 ]
  3. LE Lain R, Barrell KJ, Saeed GS, Nicholls PJ, Simons C, Kirby A, Smith HJ: Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme. J Enzyme Inhib Med Chem. 2002 Apr;17(2):93-100. [PubMed:12420755 ]
  4. Vorum H, Fisker K, Brodersen R: High-affinity binding of two molecules of warfarin and phenprocoumon to human serum albumin. Biochim Biophys Acta. 1994 Apr 13;1205(2):178-82. [PubMed:8155695 ]

Enzymes

Enzyme Details
1. Lactoperoxidase
General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
Enzyme Details
2. Peroxiredoxin-6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
4-Coumaryl alcohol → p-Hydroxyphenyl lignindetails
Enzyme Details
3. Myeloperoxidase
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
Enzyme Details
4. Eosinophil peroxidase
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5
Enzyme Details
5. Sulfotransferase family cytosolic 2B member 1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
4-Coumaryl alcohol → {[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]oxy}sulfonic aciddetails
Enzyme Details
6. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Coumaryl alcohol → 3,4,5-trihydroxy-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]phenoxy}oxane-2-carboxylic aciddetails
Enzyme Details
7. 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
4-Coumaryl alcohol → {4-[(1E)-3-hydroxyprop-1-en-1-yl]phenyl}oxidanesulfonic aciddetails