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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:25 UTC

Update Date

2023-02-21 17:21:01 UTC

HMDB ID

HMDB0031622

Secondary Accession Numbers

HMDB31622

Metabolite Identification

Common Name

6-Phenyl-3-hexen-2-one

Description

6-Phenyl-3-hexen-2-one belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review very few articles have been published on 6-Phenyl-3-hexen-2-one.

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       2.667   9.240   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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    3   12                                                       
CONECT    9    4   12                                                       
CONECT   10    6   12                                                       
CONECT   11    1    7   13                                                  
CONECT   12    8    9   10                                                  
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0031622
HETATM    1  C1  UNL     1      -4.777   0.228  -0.203  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.940  -0.007  -1.403  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.479  -0.008  -2.536  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.504  -0.240  -1.329  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.855  -0.254  -0.161  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.389  -0.495  -0.121  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.348   0.670   0.499  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.792   0.367   0.507  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.544   0.742  -0.582  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.909   0.463  -0.591  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.514  -0.178   0.465  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.728  -0.542   1.547  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.376  -0.271   1.565  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.759   1.297   0.121  1.00  0.00           H  
HETATM   15  H2  UNL     1      -5.830  -0.044  -0.360  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.403  -0.362   0.668  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.893  -0.411  -2.200  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.383  -0.094   0.747  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.014  -0.784  -1.097  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.244  -1.388   0.549  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.014   0.813   1.537  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.149   1.595  -0.087  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.092   1.245  -1.421  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.496   0.751  -1.431  1.00  0.00           H  
HETATM   25  H12 UNL     1       5.572  -0.405   0.481  1.00  0.00           H  
HETATM   26  H13 UNL     1       4.144  -1.047   2.405  1.00  0.00           H  
HETATM   27  H14 UNL     1       1.791  -0.571   2.431  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5    5   17
CONECT    5    6   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3E)-6-Phenyl-3-hexen-2-one	HMDB
6-Phenylhex-3-en-2-one	HMDB

Chemical Formula

C₁₂H₁₄O

Average Molecular Weight

174.239

Monoisotopic Molecular Weight

174.10446507

IUPAC Name

(3E)-6-phenylhex-3-en-2-one

Traditional Name

(3E)-6-phenylhex-3-en-2-one

CAS Registry Number

33046-41-2

SMILES

CC(=O)\C=C\CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H14O/c1-11(13)7-5-6-10-12-8-3-2-4-9-12/h2-5,7-9H,6,10H2,1H3/b7-5+

InChI Key

PHEPHOADHFLZJS-FNORWQNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031622)
Cell membrane (HMDB: HMDB0031622)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031622)

Source

Endogenous

Endogenous (HMDB: HMDB0031622)

Exogenous

Food

Food (HMDB: HMDB0031622)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0031622)

Process

Not Available

Role

Not Available

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	154.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	19.85	ChemAxon
pKa (Strongest Basic)	-4.6	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	55.81 m³·mol⁻¹	ChemAxon
Polarizability	20.69 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
DeepCCS	[M+H]+	136.632	30932474
DeepCCS	[M-H]-	134.082	30932474
DeepCCS	[M-2H]-	169.822	30932474
DeepCCS	[M+Na]+	144.471	30932474
AllCCS	[M+H]+	138.1	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	141.7	32859911
AllCCS	[M+Na-2H]-	142.5	32859911
AllCCS	[M+HCOO]-	143.5	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.	8.11 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3773 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2206.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	545.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	212.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	358.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	687.4 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	685.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1506.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	556.3 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	1431.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	442.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	423.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	446.3 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Phenyl-3-hexen-2-one	CC(=O)\C=C\CCC1=CC=CC=C1	2235.5	Standard polar	33892256
6-Phenyl-3-hexen-2-one	CC(=O)\C=C\CCC1=CC=CC=C1	1448.1	Standard non polar	33892256
6-Phenyl-3-hexen-2-one	CC(=O)\C=C\CCC1=CC=CC=C1	1483.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Phenyl-3-hexen-2-one,1TMS,isomer #1	C=C(/C=C/CCC1=CC=CC=C1)O[Si](C)(C)C	1634.2	Semi standard non polar	33892256
6-Phenyl-3-hexen-2-one,1TMS,isomer #1	C=C(/C=C/CCC1=CC=CC=C1)O[Si](C)(C)C	1563.6	Standard non polar	33892256
6-Phenyl-3-hexen-2-one,1TBDMS,isomer #1	C=C(/C=C/CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1873.5	Semi standard non polar	33892256
6-Phenyl-3-hexen-2-one,1TBDMS,isomer #1	C=C(/C=C/CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	1815.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Phenyl-3-hexen-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-59a8c12f57f465bcde4b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Phenyl-3-hexen-2-one 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 - 6-Phenyl-3-hexen-2-one 10V, Positive-QTOF	splash10-056r-0900000000-711080af081bd51c0238	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 20V, Positive-QTOF	splash10-0ar0-4900000000-b4d2803b92adaf2104e3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 40V, Positive-QTOF	splash10-0fr6-9300000000-1d3c926197318dbdae79	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 10V, Negative-QTOF	splash10-00di-0900000000-ef97d049b176c5dfc077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 20V, Negative-QTOF	splash10-00di-0900000000-6a2dd2ab5a6f033cb93d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 40V, Negative-QTOF	splash10-0a6u-7900000000-8d4fb139011b04fc617e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 10V, Positive-QTOF	splash10-05r0-2900000000-e6e73f365d72f31eec7e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 20V, Positive-QTOF	splash10-00mo-9600000000-019f7f3d8cb28f0a3e3b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 40V, Positive-QTOF	splash10-002f-9300000000-27074692a0729acafcca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 10V, Negative-QTOF	splash10-00di-0900000000-7e348a3518409b2410fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 20V, Negative-QTOF	splash10-05fr-2900000000-837d620dd1e24e17a6e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Phenyl-3-hexen-2-one 40V, Negative-QTOF	splash10-0f96-9300000000-dc8a12d65fc7a726611d	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]+)	2023-02-04	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

Membrane

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

FDB008260

KNApSAcK ID

C00057348

Chemspider ID

4519727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5368427

PDB ID

Not Available

ChEBI ID

169674

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827271

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 6-Phenyl-3-hexen-2-one (HMDB0031622)

MOL for HMDB0031622 (6-Phenyl-3-hexen-2-one)

3D MOL for HMDB0031622 (6-Phenyl-3-hexen-2-one)

3D SDF for HMDB0031622 (6-Phenyl-3-hexen-2-one)

3D-SDF for HMDB0031622 (6-Phenyl-3-hexen-2-one)

PDB for HMDB0031622 (6-Phenyl-3-hexen-2-one)

3D PDB for HMDB0031622 (6-Phenyl-3-hexen-2-one)

SMILES for HMDB0031622 (6-Phenyl-3-hexen-2-one)

INCHI for HMDB0031622 (6-Phenyl-3-hexen-2-one)

Structure for HMDB0031622 (6-Phenyl-3-hexen-2-one)

3D Structure for HMDB0031622 (6-Phenyl-3-hexen-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra