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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 18:36:06 UTC

Update Date

2023-02-21 17:23:39 UTC

HMDB ID

HMDB0033827

Secondary Accession Numbers

HMDB33827

Metabolite Identification

Common Name

(2E)-2-Heptenal

Description

(2E)-2-Heptenal, also known as 3-butylacrolein or 2-trans-heptenal, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. (2E)-2-Heptenal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (2E)-2-heptenal is considered to be a fatty aldehyde lipid molecule. Uremic toxins such as 2-Heptenal are actively transported into the kidneys via organic ion transporters (especially OAT3). (2E)-2-Heptenal is an almond, and fatty tasting compound. (2E)-2-Heptenal is found, on average, in the highest concentration within safflowers. (2E)-2-Heptenal has also been detected, but not quantified, in several different foods, such as roselles, common grapes, cucumbers, garden tomato, and evergreen blackberries. (2E)-2-Heptenal is a potentially toxic compound. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. As a uremic toxin, this compound can cause uremic syndrome. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2E)-Heptenal	ChEBI
(e)-2-Hepten-1-al	ChEBI
2-trans-Heptenal	ChEBI
3-Butylacrolein	ChEBI
beta-Butylacrolein	ChEBI
Hept-(e)-2-enal	ChEBI
Hept-2(e)-enal	ChEBI
Hept-trans-2-enal	ChEBI
N-Hept-trans-2-enal	ChEBI
trans-2-Hepten-1-al	ChEBI
trans-2-Heptenal	ChEBI
b-Butylacrolein	Generator
Β-butylacrolein	Generator
(e)-2-Heptenal	ChEMBL, HMDB
2-Hept-enal	HMDB
alpha-Heptenal	HMDB
Butylacrolein	HMDB
FEMA 3165	HMDB
2-Heptenal, (e)-isomer	MeSH, HMDB
2-Heptenal	MeSH

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

(2E)-hept-2-enal

Traditional Name

2-heptenal, (2E)-

CAS Registry Number

2463-63-0

SMILES

CCCC\C=C\C=O

InChI Identifier

InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h5-7H,2-4H2,1H3/b6-5+

InChI Key

NDFKTBCGKNOHPJ-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000019 )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Kidney disease (HMDB: HMDB0033827)
Uremia (HMDB: HMDB0033827)
Chronic kidney disease (HMDB: HMDB0033827)

Observation

Nervous system disorder

Coma (HMDB: HMDB0033827)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0033827)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0033827)

Organoleptic effect

Odor

Taste

Pungent

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0033827)
Extracellular (HMDB: HMDB0033827)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0033827)
Saliva (HMDB: HMDB0033827)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0033827)

Enteral

Ingestion (HMDB: HMDB0033827)

Source

Exogenous

Exogenous (HMDB: HMDB0033827)

Food

Food (HMDB: HMDB0033827)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Flat bread

Tortilla (FooDB: FOOD00709)

Gourd

Cucumber (FooDB: FOOD00065)
Watermelon (FooDB: FOOD00052)

Herb and spice

Oilseed crop

Safflower (FooDB: FOOD00042)

Herb

Roselle (FooDB: FOOD00447)

Taco (FooDB: FOOD00708)

Endogenous

Plant

Fabaceae (HMDB: HMDB0033827)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033827)

Biological role

Nutrient (HMDB: HMDB0033827)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	90.00 to 91.00 °C. @ 50.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	2.300 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.2	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	35.84 m³·mol⁻¹	ChemAxon
Polarizability	13.59 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]+	126.816	31661259
DarkChem	[M-H]-	122.46	31661259
DeepCCS	[M+H]+	130.884	30932474
DeepCCS	[M-H]-	128.989	30932474
DeepCCS	[M-2H]-	164.668	30932474
DeepCCS	[M+Na]+	139.189	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.3	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	131.4	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	138.1	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.	4.92 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4814 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1959.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	517.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	393.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	652.3 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	644.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	203.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1314.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.7 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	1358.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	488.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	616.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	550.9 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	42.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2E)-2-Heptenal	CCCC\C=C\C=O	1279.3	Standard polar	33892256
(2E)-2-Heptenal	CCCC\C=C\C=O	921.0	Standard non polar	33892256
(2E)-2-Heptenal	CCCC\C=C\C=O	948.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (2E)-2-Heptenal EI-B (Non-derivatized)	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (2E)-2-Heptenal EI-B (Non-derivatized)	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E)-2-Heptenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-9000000000-5dedb721b6e6ec596371	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2E)-2-Heptenal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-78a71f46d13bfca3d317	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 - (2E)-2-Heptenal 10V, Positive-QTOF	splash10-03di-6900000000-4a2743833647b0bdb535	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Positive-QTOF	splash10-03dj-9400000000-6ff3124de5daea2c5dc7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Positive-QTOF	splash10-0k96-9000000000-21a1a7ea291def5b6e29	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Negative-QTOF	splash10-03di-1900000000-316d71b866cb472295ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Negative-QTOF	splash10-03di-4900000000-af5169f2777e09a2d955	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Negative-QTOF	splash10-0006-9000000000-144150625b2c04635793	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Negative-QTOF	splash10-03di-3900000000-914db82f697f24d29d0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Negative-QTOF	splash10-0006-9200000000-ac71f7a8d0b92d89ca07	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Negative-QTOF	splash10-0rkc-9000000000-de34104ae53e4248a8d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 10V, Positive-QTOF	splash10-0a4i-9000000000-8d02e35f9ff6d556c0bb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 20V, Positive-QTOF	splash10-066u-9000000000-aa11d319dd6879fab78a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2E)-2-Heptenal 40V, Positive-QTOF	splash10-0673-9000000000-46f63dfa7a32f461d5ac	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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]+)	2023-02-04	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

Blood
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.16 +/- 0.05 uM	Adult (>18 years old)	Both	Normal	22626821	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.49 +/- 0.15 uM	Adult (>18 years old)	Both	uremia	22626821	details

Associated Disorders and Diseases

Disease References

Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008060

KNApSAcK ID

C00034755

Chemspider ID

4446437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283316

PDB ID

Not Available

ChEBI ID

143912

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029828

Good Scents ID

rw1028241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (2E)-2-Heptenal (HMDB0033827)

MOL for HMDB0033827 ((2E)-2-Heptenal)

3D MOL for HMDB0033827 ((2E)-2-Heptenal)

3D SDF for HMDB0033827 ((2E)-2-Heptenal)

3D-SDF for HMDB0033827 ((2E)-2-Heptenal)

PDB for HMDB0033827 ((2E)-2-Heptenal)

3D PDB for HMDB0033827 ((2E)-2-Heptenal)

SMILES for HMDB0033827 ((2E)-2-Heptenal)

INCHI for HMDB0033827 ((2E)-2-Heptenal)

Structure for HMDB0033827 ((2E)-2-Heptenal)

3D Structure for HMDB0033827 ((2E)-2-Heptenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra