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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:03 UTC

Update Date

2023-02-21 17:21:15 UTC

HMDB ID

HMDB0031725

Secondary Accession Numbers

HMDB31725

Metabolite Identification

Common Name

(E)-3-(2-Hydroxyphenyl)-2-propenal

Description

(E)-3-(2-Hydroxyphenyl)-2-propenal belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal (E)-3-(2-Hydroxyphenyl)-2-propenal has been detected, but not quantified in, chinese cinnamons (Cinnamomum aromaticum). This could make (e)-3-(2-hydroxyphenyl)-2-propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-3-(2-Hydroxyphenyl)-2-propenal.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₈O₂

Average Molecular Weight

148.1586

Monoisotopic Molecular Weight

148.0524295

IUPAC Name

(2E)-3-(2-hydroxyphenyl)prop-2-enal

Traditional Name

(2E)-3-(2-hydroxyphenyl)prop-2-enal

CAS Registry Number

60125-23-7

SMILES

OC1=CC=CC=C1\C=C\C=O

InChI Identifier

InChI=1S/C9H8O2/c10-7-3-5-8-4-1-2-6-9(8)11/h1-7,11H/b5-3+

InChI Key

BSDNZCQPDVTDET-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated aldehyde
Enal
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031725)
Cytoplasm (HMDB: HMDB0031725)

Source

Exogenous

Exogenous (HMDB: HMDB0031725)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0031725)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131 - 132 °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	2.14 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.67	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.12 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	131.146	30932474
DeepCCS	[M-H]-	128.572	30932474
DeepCCS	[M-2H]-	164.84	30932474
DeepCCS	[M+Na]+	139.888	30932474
AllCCS	[M+H]+	131.0	32859911
AllCCS	[M+H-H2O]+	126.4	32859911
AllCCS	[M+NH4]+	135.3	32859911
AllCCS	[M+Na]+	136.5	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	129.9	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	4.23 minutes	32390414
Predicted by Siyang on May 30, 2022	10.735 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1629.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	353.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	227.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	156.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	492.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	491.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1023.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	355.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1012.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	280.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	475.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	300.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	66.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-(2-Hydroxyphenyl)-2-propenal	OC1=CC=CC=C1\C=C\C=O	2320.3	Standard polar	33892256
(E)-3-(2-Hydroxyphenyl)-2-propenal	OC1=CC=CC=C1\C=C\C=O	1410.5	Standard non polar	33892256
(E)-3-(2-Hydroxyphenyl)-2-propenal	OC1=CC=CC=C1\C=C\C=O	1484.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-(2-Hydroxyphenyl)-2-propenal,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CC=C1/C=C/C=O	1654.1	Semi standard non polar	33892256
(E)-3-(2-Hydroxyphenyl)-2-propenal,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC=C1/C=C/C=O	1905.7	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 - (E)-3-(2-Hydroxyphenyl)-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-2900000000-ac2eb21d29159860eb58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-6930000000-181d7583f47bf2b68a92	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 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 - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Positive-QTOF	splash10-0002-0900000000-aaea5a64a4ae76da2733	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Positive-QTOF	splash10-000t-4900000000-f5a22f9b719e2cf3c809	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Positive-QTOF	splash10-0a6u-9300000000-c4624fa0468fab374cf2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Negative-QTOF	splash10-0002-0900000000-7f812f78efb7808aece3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Negative-QTOF	splash10-0002-1900000000-c88971a408cfdc0b27a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Negative-QTOF	splash10-0006-9400000000-36c8dbc04c63542f182d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Negative-QTOF	splash10-014i-0900000000-972f865a96261dcb891a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Negative-QTOF	splash10-014i-0900000000-06171ad407ac98e9b2a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Negative-QTOF	splash10-014i-9300000000-2cbda1718cb4dbcce012	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 10V, Positive-QTOF	splash10-0592-0900000000-37cf9ecd0820f286aeed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 20V, Positive-QTOF	splash10-0zfr-3900000000-8b807998f5cd06d1ab9f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Hydroxyphenyl)-2-propenal 40V, Positive-QTOF	splash10-0udi-7900000000-6b921145859c90c4715d	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

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

FDB011996

KNApSAcK ID

Not Available

Chemspider ID

4476786

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318169

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. 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

(E)-3-(2-Hydroxyphenyl)-2-propenal → 3,4,5-trihydroxy-6-{2-[(1E)-3-oxoprop-1-en-1-yl]phenoxy}oxane-2-carboxylic acid	details

Showing metabocard for (E)-3-(2-Hydroxyphenyl)-2-propenal (HMDB0031725)

MOL for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

3D MOL for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

3D SDF for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

3D-SDF for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

PDB for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

3D PDB for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

SMILES for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

INCHI for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

Structure for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

3D Structure for HMDB0031725 ((E)-3-(2-Hydroxyphenyl)-2-propenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions