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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-08-13 02:37:06 UTC

Update Date

2023-02-21 17:16:46 UTC

HMDB ID

HMDB0003654

Secondary Accession Numbers

HMDB03654

Metabolite Identification

Common Name

4-Coumaryl alcohol

Description

4-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(E)-4-Coumaryl alcohol	ChEBI, HMDB
4-Hydroxycinnamyl alcohol	ChEBI
p-Coumaryl alcohol	ChEBI
3-(4-Hydroxyphenyl)-1-propane	HMDB
3-OHPP	HMDB
4-Coumarinol	HMDB
4-Hydroxy-2H-1-benzopyran-2-one	HMDB
4-Hydroxy-2H-chromen-2-one	HMDB
4-Hydroxycoumarin	HMDB
4-Hydroxycoumarine	HMDB
Benzotetronate	HMDB
Benzotetronic acid	HMDB
Hydroxy coumarin	HMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acid	MeSH, HMDB
trans-HPPA	MeSH, HMDB
p-Hydroxycinnamic acid	MeSH, HMDB
Para-coumaric acid	MeSH, HMDB
4-Coumaric acid, (E)-isomer	MeSH, HMDB
4-Hydroxycinnamic acid	MeSH, HMDB
p-Coumaric acid	MeSH, HMDB
4-Coumaric acid	MeSH, HMDB
(E)-4-Coumaroyl alcohol	ChEBI
(E)-p-Coumaryl alcohol	HMDB
3-(p-Hydroxyphenyl)-2-propen-1-ol	HMDB
4-(3-Hydroxy-1-propen-1-yl)phenol	HMDB
4-Coumaryl alcohol	HMDB
4-Hydroxycinnamic alcohol	HMDB
4-[(1E)-3-Hydroxy-1-propenyl]phenol	HMDB
Paracoumaryl alcohol	HMDB
p-Coumaric alcohol	HMDB
p-Cumaric alcohol	HMDB
p-Hydroxycinnamic alcohol	HMDB
p-Hydroxycinnamyl alcohol	HMDB
trans-p-Coumaryl alcohol	HMDB

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

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

Traditional Name

paracoumaryl alcohol

CAS Registry Number

20649-40-5

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 Key

PTNLHDGQWUGONS-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:64555 )
phenylpropanoid (CHEBI:64555 )
4-hydroxycinnamyl alcohol (CHEBI:64555 )
Paracoumaryl alcohol derivatives (C02646 )

Ontology

Not Available

Testicle (HMDB: HMDB0003654)

Cellular substructure

Cytoplasm (HMDB: HMDB0003654)
Extracellular (HMDB: HMDB0003654)

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.97 g/L	ALOGPS
logP	1.55	ALOGPS
logP	1.51	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.17 m³·mol⁻¹	ChemAxon
Polarizability	16.35 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.85	31661259
DarkChem	[M-H]-	132.942	31661259
DeepCCS	[M+H]+	134.701	30932474
DeepCCS	[M-H]-	130.873	30932474
DeepCCS	[M-2H]-	168.524	30932474
DeepCCS	[M+Na]+	144.063	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.5	32859911
AllCCS	[M+NH4]+	136.3	32859911
AllCCS	[M+Na]+	137.5	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	133.2	32859911
AllCCS	[M+HCOO]-	134.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaryl alcohol	OC\C=C\C1=CC=C(O)C=C1	2766.9	Standard polar	33892256
4-Coumaryl alcohol	OC\C=C\C1=CC=C(O)C=C1	1598.2	Standard non polar	33892256
4-Coumaryl alcohol	OC\C=C\C1=CC=C(O)C=C1	1655.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaryl alcohol,1TMS,isomer #1	C[Si](C)(C)OC/C=C/C1=CC=C(O)C=C1	1739.9	Semi standard non polar	33892256
4-Coumaryl alcohol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/CO)C=C1	1652.2	Semi standard non polar	33892256
4-Coumaryl alcohol,2TMS,isomer #1	C[Si](C)(C)OC/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	1817.4	Semi standard non polar	33892256
4-Coumaryl alcohol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC/C=C/C1=CC=C(O)C=C1	1993.9	Semi standard non polar	33892256
4-Coumaryl alcohol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/CO)C=C1	1912.4	Semi standard non polar	33892256
4-Coumaryl alcohol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2289.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0l1i-2900000000-35b232588497df392bcc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (2 TMS) - 70eV, Positive	splash10-00fu-9360000000-71f6e35237794477c995	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaryl alcohol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Positive-QTOF	splash10-0f89-0900000000-d0aa38e43ffe69c65dce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Positive-QTOF	splash10-001i-1900000000-f35b26b4169e49f89651	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Positive-QTOF	splash10-0a4r-9600000000-feffeb0ec4d7bfd7e421	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Negative-QTOF	splash10-0002-0900000000-aa3fec540eb5ff87fecf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Negative-QTOF	splash10-0002-0900000000-926f68e15b016ddc1bf9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Negative-QTOF	splash10-05nf-6900000000-53b966254d033e195810	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Positive-QTOF	splash10-0a59-0900000000-ef3175d0cc2e2c422a13	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Positive-QTOF	splash10-0ae9-4900000000-512eaa23bb6e2ec1bf3b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Positive-QTOF	splash10-004i-9200000000-835e5fb65c2a8f70004b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 10V, Negative-QTOF	splash10-014j-0900000000-8d131986ef2454e28919	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 20V, Negative-QTOF	splash10-0159-0900000000-c01ea2304d08f2059c07	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaryl alcohol 40V, Negative-QTOF	splash10-014i-3900000000-6bda1a3cbe19b1fee9f7	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

64555

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Takahashi, 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

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 ]
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 ]
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 ]
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 lignin	details

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 acid	details

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 acid	details

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 acid	details

Showing metabocard for 4-Coumaryl alcohol (HMDB0003654)

MOL for HMDB0003654 (4-Coumaryl alcohol)

3D MOL for HMDB0003654 (4-Coumaryl alcohol)

3D SDF for HMDB0003654 (4-Coumaryl alcohol)

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

PDB for HMDB0003654 (4-Coumaryl alcohol)

3D PDB for HMDB0003654 (4-Coumaryl alcohol)

SMILES for HMDB0003654 (4-Coumaryl alcohol)

INCHI for HMDB0003654 (4-Coumaryl alcohol)

Structure for HMDB0003654 (4-Coumaryl alcohol)

3D Structure for HMDB0003654 (4-Coumaryl alcohol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions