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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:43:22 UTC

Update Date

2023-02-21 17:20:34 UTC

HMDB ID

HMDB0031454

Secondary Accession Numbers

HMDB31454

Metabolite Identification

Common Name

trans-Jasmone

Description

trans-Jasmone is found in spearmint. Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Wikipedia

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.905  -8.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.151  -9.660   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.675 -11.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.135 -11.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.659  -9.660   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.905  -7.215   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.230 -12.371   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.194  -9.184   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.874  -7.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.590  -7.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.910  -5.696   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.375  -5.220   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    1    8                                                  
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0031454
HETATM    1  C1  UNL     1       4.527  -0.480   0.287  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.350   0.429   0.442  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.236  -0.038  -0.442  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.051  -0.395   0.028  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.062  -0.860  -0.843  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.250   0.042  -0.694  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.446  -0.352  -0.275  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.785  -1.765   0.114  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.366   0.801  -0.267  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.424   1.976  -0.189  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.275   1.468  -0.976  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.492   2.092  -1.717  1.00  0.00           O  
HETATM   13  H1  UNL     1       4.627  -0.821  -0.758  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.408  -1.337   0.977  1.00  0.00           H  
HETATM   15  H3  UNL     1       5.458   0.061   0.566  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.669   1.453   0.114  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.050   0.486   1.494  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.426  -0.078  -1.506  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.936  -0.326   1.121  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.316  -1.905  -0.641  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.315  -0.813  -1.886  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.606  -1.672   0.874  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.181  -2.310  -0.790  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.922  -2.277   0.560  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.848   0.840  -1.264  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.091   0.778   0.563  1.00  0.00           H  
HETATM   27  H15 UNL     1      -2.854   2.900  -0.622  1.00  0.00           H  
HETATM   28  H16 UNL     1      -2.137   2.102   0.886  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4    4   18
CONECT    4    5   19
CONECT    5    6   20   21
CONECT    6    7    7   11
CONECT    7    8    9
CONECT    8   22   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   12
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-Jasmone	HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (e)- (8ci)	HMDB
3-Methyl-2-(2E)-2-penten-1-yl-2-cyclopenten-1-one	HMDB
3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one	MeSH

Chemical Formula

C₁₁H₁₆O

Average Molecular Weight

164.2441

Monoisotopic Molecular Weight

164.120115134

IUPAC Name

3-methyl-2-[(2E)-pent-2-en-1-yl]cyclopent-2-en-1-one

Traditional Name

3-methyl-2-[(2E)-pent-2-en-1-yl]cyclopent-2-en-1-one

CAS Registry Number

6261-18-3

SMILES

CC\C=C\CC1=C(C)CCC1=O

InChI Identifier

InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4+

InChI Key

XMLSXPIVAXONDL-SNAWJCMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031454)
Cell membrane (HMDB: HMDB0031454)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 20809147)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031454)

Source

Endogenous

Endogenous (HMDB: HMDB0031454)

Plant

Plant (HMDB: HMDB0031454)

Exogenous

Food

Food (HMDB: HMDB0031454)

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Exogenous (HMDB: HMDB0031454)

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	263.00 to 265.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	60.54 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.905 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.8	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	3	ChemAxon
Refractivity	52.9 m³·mol⁻¹	ChemAxon
Polarizability	19.89 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]+	140.493	31661259
DarkChem	[M-H]-	135.576	31661259
DeepCCS	[M+H]+	143.771	30932474
DeepCCS	[M-H]-	139.944	30932474
DeepCCS	[M-2H]-	177.026	30932474
DeepCCS	[M+Na]+	152.565	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	141.5	32859911
AllCCS	[M+Na-2H]-	142.7	32859911
AllCCS	[M+HCOO]-	144.2	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.	6.99 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5487 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2218.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	532.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	209.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	362.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.3 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	654.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1428.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	474.9 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	1299.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	393.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	515.4 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
trans-Jasmone	CC\C=C\CC1=C(C)CCC1=O	1952.4	Standard polar	33892256
trans-Jasmone	CC\C=C\CC1=C(C)CCC1=O	1366.8	Standard non polar	33892256
trans-Jasmone	CC\C=C\CC1=C(C)CCC1=O	1372.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
trans-Jasmone,1TMS,isomer #1	CC/C=C/CC1=C(C)CC=C1O[Si](C)(C)C	1520.0	Semi standard non polar	33892256
trans-Jasmone,1TMS,isomer #1	CC/C=C/CC1=C(C)CC=C1O[Si](C)(C)C	1519.6	Standard non polar	33892256
trans-Jasmone,1TBDMS,isomer #1	CC/C=C/CC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C	1748.1	Semi standard non polar	33892256
trans-Jasmone,1TBDMS,isomer #1	CC/C=C/CC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C	1685.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Jasmone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-6900000000-4ec9a03205a62c5db571	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Jasmone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - trans-Jasmone 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 - trans-Jasmone 10V, Positive-QTOF	splash10-014i-1900000000-b3455ba1815cd60172a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 20V, Positive-QTOF	splash10-066r-7900000000-df4da4ed2a4217531361	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 40V, Positive-QTOF	splash10-0uxu-9100000000-1ad974119b61c19d8fcb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 10V, Negative-QTOF	splash10-03di-0900000000-54214296816474e67819	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 20V, Negative-QTOF	splash10-03di-0900000000-9e2bcdc11fb8c55163ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 40V, Negative-QTOF	splash10-0006-9800000000-3aa25aca2cc0986b4e11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 10V, Negative-QTOF	splash10-03di-0900000000-defd12a7f890bc945918	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 20V, Negative-QTOF	splash10-03di-0900000000-7005ce6951d5a76167cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 40V, Negative-QTOF	splash10-066r-4900000000-524d8ff912c0d662ad37	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 10V, Positive-QTOF	splash10-0900-5900000000-150eb84c8131eaddd806	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 20V, Positive-QTOF	splash10-052f-9300000000-4c74719ab790c3d97cb7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - trans-Jasmone 40V, Positive-QTOF	splash10-0536-9000000000-eac87e59851b2c86a210	2021-09-25	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

Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

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

FDB006131

KNApSAcK ID

Not Available

Chemspider ID

1266013

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1549019

PDB ID

Not Available

ChEBI ID

88585

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1459321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for trans-Jasmone (HMDB0031454)

MOL for HMDB0031454 (trans-Jasmone)

3D MOL for HMDB0031454 (trans-Jasmone)

3D SDF for HMDB0031454 (trans-Jasmone)

3D-SDF for HMDB0031454 (trans-Jasmone)

PDB for HMDB0031454 (trans-Jasmone)

3D PDB for HMDB0031454 (trans-Jasmone)

SMILES for HMDB0031454 (trans-Jasmone)

INCHI for HMDB0031454 (trans-Jasmone)

Structure for HMDB0031454 (trans-Jasmone)

3D Structure for HMDB0031454 (trans-Jasmone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra