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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:20 UTC

Update Date

2023-02-21 17:22:18 UTC

HMDB ID

HMDB0032536

Secondary Accession Numbers

HMDB32536

Metabolite Identification

Common Name

2-(trans-2-Pentenyl)cyclopentanone

Description

2-(trans-2-Pentenyl)cyclopentanone, also known as (e)-2-(pent-2-enyl)cyclopentan-1-one, 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. Based on a literature review very few articles have been published on 2-(trans-2-Pentenyl)cyclopentanone.

Structure

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

COMPND    HMDB0032536
HETATM    1  C1  UNL     1       4.525   0.435   0.329  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.316   0.518  -0.580  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.204  -0.321  -0.123  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.022   0.250   0.174  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.127  -0.557   0.639  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.269  -0.405  -0.306  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.477  -1.231   0.140  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.590  -0.535  -0.614  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.329   0.910  -0.165  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.835   0.958  -0.394  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.168   1.955  -0.619  1.00  0.00           O  
HETATM   12  H1  UNL     1       5.328   1.046  -0.178  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.321   0.899   1.310  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.896  -0.613   0.432  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.017   1.571  -0.632  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.628   0.175  -1.585  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.272  -1.390  -0.005  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.953   1.322   0.059  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.145  -1.635   0.661  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.415  -0.229   1.657  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.000  -0.802  -1.311  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.379  -2.289  -0.125  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.641  -1.105   1.245  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.389  -0.636  -1.686  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.589  -0.867  -0.308  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.865   1.629  -0.783  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.552   0.944   0.908  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4    4   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   10   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   11
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2-(Pent-2-enyl)cyclopentan-1-one	HMDB
2-(2E)-2-Penten-1-yl-cyclopentanone	HMDB
2-(2E)-2-Pentenyl-cyclopentanone	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-[(2E)-pent-2-en-1-yl]cyclopentan-1-one

Traditional Name

2-[(2E)-pent-2-en-1-yl]cyclopentan-1-one

CAS Registry Number

51608-18-5

SMILES

CC\C=C\CC1CCCC1=O

InChI Identifier

InChI=1S/C10H16O/c1-2-3-4-6-9-7-5-8-10(9)11/h3-4,9H,2,5-8H2,1H3/b4-3+

InChI Key

ZIJOSCABGITYIL-ONEGZZNKSA-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

Cellular substructure

Membrane (HMDB: HMDB0032536)
Cell membrane (HMDB: HMDB0032536)

Source

Endogenous

Endogenous (HMDB: HMDB0032536)

Exogenous

Food

Food (HMDB: HMDB0032536)

Exogenous (HMDB: HMDB0032536)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	3	ALOGPS
logP	3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-7.4	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	47.74 m³·mol⁻¹	ChemAxon
Polarizability	18.52 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
DarkChem	[M+H]+	137.423	31661259
DarkChem	[M-H]-	134.335	31661259
DeepCCS	[M+H]+	137.207	30932474
DeepCCS	[M-H]-	133.697	30932474
DeepCCS	[M-2H]-	170.775	30932474
DeepCCS	[M+Na]+	145.961	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	139.4	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.6	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.	5.68 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5302 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2088.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	490.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	331.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	621.1 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	565.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1366.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	434.2 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	1258.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	393.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	429.1 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	12.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(trans-2-Pentenyl)cyclopentanone	CC\C=C\CC1CCCC1=O	1731.0	Standard polar	33892256
2-(trans-2-Pentenyl)cyclopentanone	CC\C=C\CC1CCCC1=O	1216.3	Standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone	CC\C=C\CC1CCCC1=O	1246.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(trans-2-Pentenyl)cyclopentanone,1TMS,isomer #1	CC/C=C/CC1=C(O[Si](C)(C)C)CCC1	1395.5	Semi standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TMS,isomer #1	CC/C=C/CC1=C(O[Si](C)(C)C)CCC1	1419.4	Standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TMS,isomer #2	CC/C=C/CC1CCC=C1O[Si](C)(C)C	1359.3	Semi standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TMS,isomer #2	CC/C=C/CC1CCC=C1O[Si](C)(C)C	1413.0	Standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TBDMS,isomer #1	CC/C=C/CC1=C(O[Si](C)(C)C(C)(C)C)CCC1	1633.6	Semi standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TBDMS,isomer #1	CC/C=C/CC1=C(O[Si](C)(C)C(C)(C)C)CCC1	1600.5	Standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TBDMS,isomer #2	CC/C=C/CC1CCC=C1O[Si](C)(C)C(C)(C)C	1597.9	Semi standard non polar	33892256
2-(trans-2-Pentenyl)cyclopentanone,1TBDMS,isomer #2	CC/C=C/CC1CCC=C1O[Si](C)(C)C(C)(C)C	1561.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05te-9500000000-65271d3a4686c4775070	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 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-(trans-2-Pentenyl)cyclopentanone 10V, Positive-QTOF	splash10-0udi-1900000000-03f7598a020c790290fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 20V, Positive-QTOF	splash10-0zir-9400000000-b0e48582d9a23416e9c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 40V, Positive-QTOF	splash10-0f6x-9000000000-9c4f8f44d7d12c5b359e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 10V, Negative-QTOF	splash10-0udi-0900000000-269f4f5aa911452c2014	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 20V, Negative-QTOF	splash10-0udi-1900000000-75b8cbeb7e39021c44c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 40V, Negative-QTOF	splash10-000x-9300000000-419f156ff753a72ef449	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 20V, Negative-QTOF	splash10-0udi-1900000000-b20f88c0013696dfd134	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 40V, Negative-QTOF	splash10-00ke-9300000000-a13b92197a378121a21d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 10V, Positive-QTOF	splash10-05n3-9200000000-ed2ccbb6cb75ad636470	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 20V, Positive-QTOF	splash10-05mx-9100000000-62fe5cffb29aed876a72	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(trans-2-Pentenyl)cyclopentanone 40V, Positive-QTOF	splash10-05s3-9000000000-c0d1f4e60ef59ed10cb8	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

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

FDB010406

KNApSAcK ID

Not Available

Chemspider ID

4941595

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437002

PDB ID

Not Available

ChEBI ID

171911

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

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for 2-(trans-2-Pentenyl)cyclopentanone (HMDB0032536)

MOL for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

3D MOL for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

3D SDF for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

3D-SDF for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

PDB for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

3D PDB for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

SMILES for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

INCHI for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

Structure for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

3D Structure for HMDB0032536 (2-(trans-2-Pentenyl)cyclopentanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra