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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:24:31 UTC

Update Date

2023-02-21 17:25:40 UTC

HMDB ID

HMDB0037166

Secondary Accession Numbers

HMDB37166

Metabolite Identification

Common Name

2-(Methylthiomethyl)-3-phenyl-2-propenal

Description

2-(Methylthiomethyl)-3-phenyl-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. 2-(Methylthiomethyl)-3-phenyl-2-propenal is a bean, broccoli, and green tasting compound. Based on a literature review very few articles have been published on 2-(Methylthiomethyl)-3-phenyl-2-propenal.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       4.001   6.930   0.000  0.00  0.00           S+0
CONECT    1   13                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7   10   11                                                       
CONECT    8   11   12                                                       
CONECT    9   11   13                                                       
CONECT   10    5    6    7                                                  
CONECT   11    7    8    9                                                  
CONECT   12    8                                                            
CONECT   13    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-((methylthio)Methyl)-3-phenyl-2-propenal	HMDB
2-(Methylthiomethyl)-3-phenylpropenal	HMDB
alpha-Benzylidenemethional	HMDB
(2E)-2-[(Methylsulphanyl)methyl]-3-phenylprop-2-enal	Generator

Chemical Formula

C₁₁H₁₂OS

Average Molecular Weight

192.277

Monoisotopic Molecular Weight

192.060885696

IUPAC Name

(2E)-2-[(methylsulfanyl)methyl]-3-phenylprop-2-enal

Traditional Name

(2E)-2-[(methylsulfanyl)methyl]-3-phenylprop-2-enal

CAS Registry Number

65887-08-3

SMILES

CSC\C(C=O)=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12OS/c1-13-9-11(8-12)7-10-5-3-2-4-6-10/h2-8H,9H2,1H3/b11-7+

InChI Key

QJDHQEQDIWDMOT-YRNVUSSQSA-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
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated aldehyde
Enal
Dialkylthioether
Sulfenyl compound
Thioether
Aldehyde
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037166)
Cytoplasm (HMDB: HMDB0037166)

Source

Exogenous

Exogenous (HMDB: HMDB0037166)

Food

Food (HMDB: HMDB0037166)

Endogenous

Plant

Plant (HMDB: HMDB0037166)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037166)

Biological role

Nutrient (HMDB: HMDB0037166)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.07 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.73	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.95 m³·mol⁻¹	ChemAxon
Polarizability	21.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	145.847	31661259
DarkChem	[M-H]-	142.092	31661259
DeepCCS	[M+H]+	142.696	30932474
DeepCCS	[M-H]-	139.854	30932474
DeepCCS	[M-2H]-	176.04	30932474
DeepCCS	[M+Na]+	151.578	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.7	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	144.6	32859911
AllCCS	[M+HCOO]-	145.5	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.	8.3 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1081 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.1 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2350.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	570.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	369.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	689.5 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	799.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	224.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1499.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	568.0 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	1428.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	482.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	432.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	494.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	413.3 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	18.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(Methylthiomethyl)-3-phenyl-2-propenal	CSC\C(C=O)=C\C1=CC=CC=C1	2701.5	Standard polar	33892256
2-(Methylthiomethyl)-3-phenyl-2-propenal	CSC\C(C=O)=C\C1=CC=CC=C1	1621.4	Standard non polar	33892256
2-(Methylthiomethyl)-3-phenyl-2-propenal	CSC\C(C=O)=C\C1=CC=CC=C1	1693.1	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 - 2-(Methylthiomethyl)-3-phenyl-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-6900000000-5fd2a165f5787c003a09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-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 - 2-(Methylthiomethyl)-3-phenyl-2-propenal 10V, Positive-QTOF	splash10-0006-0900000000-38fd633020ed0f44274e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 20V, Positive-QTOF	splash10-0005-2900000000-62d18d7a74954ff7aec7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 40V, Positive-QTOF	splash10-014i-9800000000-fa65d7d808ea94633dfb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 10V, Negative-QTOF	splash10-0002-9300000000-314f1cf07619a86072ee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 20V, Negative-QTOF	splash10-0002-9700000000-eaae86c9d891c3d2dd9a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 40V, Negative-QTOF	splash10-0002-9000000000-052f3f9ff5a568a06ea1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 10V, Negative-QTOF	splash10-0002-9200000000-ee7bff2b4eaff7242fe5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 20V, Negative-QTOF	splash10-0002-9000000000-8828cef2e29a5d82e1e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 40V, Negative-QTOF	splash10-0002-9200000000-74a4e5eb66515b47c148	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 10V, Positive-QTOF	splash10-014i-0900000000-99319a675c20f6598d02	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 20V, Positive-QTOF	splash10-014i-2900000000-eb23f37c3c2149a73e50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Methylthiomethyl)-3-phenyl-2-propenal 40V, Positive-QTOF	splash10-0i00-3900000000-a8f3b23b0441cbc0bc6d	2021-09-23	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+Na]+)	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

FDB016162

KNApSAcK ID

Not Available

Chemspider ID

17332793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16204499

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.. .

Showing metabocard for 2-(Methylthiomethyl)-3-phenyl-2-propenal (HMDB0037166)

MOL for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

3D MOL for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

3D SDF for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

3D-SDF for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

PDB for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

3D PDB for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

SMILES for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

INCHI for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

Structure for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

3D Structure for HMDB0037166 (2-(Methylthiomethyl)-3-phenyl-2-propenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra