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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:44:18 UTC

Update Date

2023-02-21 17:20:58 UTC

HMDB ID

HMDB0031604

Secondary Accession Numbers

HMDB31604

Metabolite Identification

Common Name

(E)-2-Penten-1-ol

Description

(E)-2-Penten-1-ol, also known as cis-pent-2-en-1-ol or 2-(Z)-pentenol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, (e)-2-penten-1-ol is considered to be a fatty alcohol (E)-2-Penten-1-ol is a green tasting compound (E)-2-Penten-1-ol has been detected, but not quantified in, asparagus (Asparagus officinalis) and broccolis (Brassica oleracea var. italica). This could make (e)-2-penten-1-ol a potential biomarker for the consumption of these foods (E)-2-Penten-1-ol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (E)-2-Penten-1-ol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2Z)-2-Penten-1-ol	ChEBI
(2Z)-Penten-1-ol	ChEBI
(Z)-2-Pentenol	ChEBI
(Z)-Pent-2-en-1-ol	ChEBI
2-(Z)-Pentenol	ChEBI
cis-2-Penten-1-ol	ChEBI
cis-2-Pentenol	ChEBI
cis-Pent-2-en-1-ol	ChEBI
cis-Pent-2-ene-1-ol	ChEBI
(e)-2-Pentenol	HMDB
2-(e)-Penten-1-ol	HMDB
2-Penten-1-ol	HMDB
Pent-2(e)-enol	HMDB
trans-2-Pentenol	HMDB

Chemical Formula

C₅H₁₀O

Average Molecular Weight

86.1323

Monoisotopic Molecular Weight

86.073164942

IUPAC Name

(2Z)-pent-2-en-1-ol

Traditional Name

(2Z)-pent-2-en-1-ol

CAS Registry Number

1576-96-1

SMILES

CC\C=C/CO

InChI Identifier

InChI=1S/C5H10O/c1-2-3-4-5-6/h3-4,6H,2,5H2,1H3/b4-3-

InChI Key

BTSIZIIPFNVMHF-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty alcohols (LMFA05000110 )

Ontology

Physiological effect

Organoleptic effect

Odor

Mushroom

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0031604)
Cytoplasm (HMDB: HMDB0031604)

Source

Exogenous

Exogenous (HMDB: HMDB0031604)

Food

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Endogenous (HMDB: HMDB0031604)

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	138.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	45720 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.146 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	54.8 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.04	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	16.08	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	27.7 m³·mol⁻¹	ChemAxon
Polarizability	10.32 Å³	ChemAxon
Number of Rings	0	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]+	118.43	31661259
DarkChem	[M-H]-	112.786	31661259
DeepCCS	[M+H]+	123.604	30932474
DeepCCS	[M-H]-	121.709	30932474
DeepCCS	[M-2H]-	156.972	30932474
DeepCCS	[M+Na]+	131.407	30932474
AllCCS	[M+H]+	122.2	32859911
AllCCS	[M+H-H2O]+	117.7	32859911
AllCCS	[M+NH4]+	126.4	32859911
AllCCS	[M+Na]+	127.7	32859911
AllCCS	[M-H]-	130.4	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	140.1	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.	2.16 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0363 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.63 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	52.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1477.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	358.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	256.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	391.8 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	415.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	109.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	889.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	334.9 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	1033.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	340.4 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	57.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Penten-1-ol	CC\C=C/CO	1254.5	Standard polar	33892256
(E)-2-Penten-1-ol	CC\C=C/CO	744.8	Standard non polar	33892256
(E)-2-Penten-1-ol	CC\C=C/CO	768.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-2-Penten-1-ol,1TMS,isomer #1	CC/C=C\CO[Si](C)(C)C	912.4	Semi standard non polar	33892256
(E)-2-Penten-1-ol,1TBDMS,isomer #1	CC/C=C\CO[Si](C)(C)C(C)(C)C	1125.2	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)-2-Penten-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05p6-9000000000-5b218a84529fbf7dacfa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Penten-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-009f-9200000000-160ff6a33ce26c5ea9f6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2-Penten-1-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-9000000000-da18eb4df2db7b17d225	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 10V, Positive-QTOF	splash10-014r-9000000000-88e1035be9943615bd74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 20V, Positive-QTOF	splash10-014i-9000000000-e1f572b289c4afa7f283	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 40V, Positive-QTOF	splash10-00kf-9000000000-da772ca175cc5e99fd58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 10V, Negative-QTOF	splash10-000i-9000000000-fbd987c498d4e8187ae6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 20V, Negative-QTOF	splash10-000i-9000000000-71c8df2b33331cefeca5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 40V, Negative-QTOF	splash10-00kf-9000000000-3da067dc653af6802c49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 10V, Positive-QTOF	splash10-014l-9000000000-c3943f4e1b8d70017189	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 20V, Positive-QTOF	splash10-0006-9000000000-9263d08b895fefaaa031	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 40V, Positive-QTOF	splash10-000f-9000000000-b7f94f42ecb6ec234644	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 10V, Negative-QTOF	splash10-000i-9000000000-2091e44a102d8284a813	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 20V, Negative-QTOF	splash10-000i-9000000000-a2aa68487a473e43ed65	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2-Penten-1-ol 40V, Negative-QTOF	splash10-0pvi-9000000000-499ee9d64becce66f8f2	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details

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

FDB008237

KNApSAcK ID

C00055766

Chemspider ID

4517028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5364919

PDB ID

Not Available

ChEBI ID

145352

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1002171

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 (E)-2-Penten-1-ol (HMDB0031604)

MOL for HMDB0031604 ((E)-2-Penten-1-ol)

3D MOL for HMDB0031604 ((E)-2-Penten-1-ol)

3D SDF for HMDB0031604 ((E)-2-Penten-1-ol)

3D-SDF for HMDB0031604 ((E)-2-Penten-1-ol)

PDB for HMDB0031604 ((E)-2-Penten-1-ol)

3D PDB for HMDB0031604 ((E)-2-Penten-1-ol)

SMILES for HMDB0031604 ((E)-2-Penten-1-ol)

INCHI for HMDB0031604 ((E)-2-Penten-1-ol)

Structure for HMDB0031604 ((E)-2-Penten-1-ol)

3D Structure for HMDB0031604 ((E)-2-Penten-1-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra