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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:36 UTC

Update Date

2023-02-21 17:20:38 UTC

HMDB ID

HMDB0031483

Secondary Accession Numbers

HMDB31483

Metabolite Identification

Common Name

(Z)-4-Heptenal

Description

(Z)-4-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 (Z)-4-Heptenal is a biscuit, creamy, and dairy tasting compound (Z)-4-Heptenal has been detected, but not quantified in, milk and milk products. This could make (Z)-4-heptenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (Z)-4-Heptenal.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
( Z)-Hept-4-enal	HMDB
(4Z)-4-Heptenal	HMDB
(Z)-4-Hepten-1-al	HMDB
4-(Z)-Heptenal	HMDB
4-Heptenal	HMDB
cis-4-Hepten-1-al	HMDB
cis-4-Heptenal	HMDB
FEMA 3289	HMDB
Hept-4(Z)-enal	HMDB
Hept-cis-4-enal	HMDB

Chemical Formula

C₇H₁₂O

Average Molecular Weight

112.1696

Monoisotopic Molecular Weight

112.088815006

IUPAC Name

(4Z)-hept-4-enal

Traditional Name

(4Z)-hept-4-enal

CAS Registry Number

6728-31-0

SMILES

CC\C=C/CCC=O

InChI Identifier

InChI=1S/C7H12O/c1-2-3-4-5-6-7-8/h3-4,7H,2,5-6H2,1H3/b4-3-

InChI Key

VVGOCOMZRGWHPI-ARJAWSKDSA-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
Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031483)
Cytoplasm (HMDB: HMDB0031483)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031483)

Source

Endogenous

Endogenous (HMDB: HMDB0031483)

Animal

Animal (HMDB: HMDB0031483)

Exogenous

Food

Food (HMDB: HMDB0031483)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0031483)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031483)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	60.00 °C. @ 30.00 mm Hg	The Good Scents Company Information System
Water Solubility	1810 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.174 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.31 g/L	ALOGPS
logP	2.09	ALOGPS
logP	1.73	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.72	ChemAxon
pKa (Strongest Basic)	-7	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	35.87 m³·mol⁻¹	ChemAxon
Polarizability	13.36 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]+	126.665	31661259
DarkChem	[M-H]-	121.864	31661259
DeepCCS	[M+H]+	130.954	30932474
DeepCCS	[M-H]-	128.872	30932474
DeepCCS	[M-2H]-	164.686	30932474
DeepCCS	[M+Na]+	139.44	30932474
AllCCS	[M+H]+	127.7	32859911
AllCCS	[M+H-H2O]+	123.4	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	131.2	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	137.9	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.	4.62 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1093 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1757.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	448.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	341.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	550.9 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	559.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	110.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1207.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	420.2 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	1160.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	434.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	486.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	472.8 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	33.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4-Heptenal	CC\C=C/CCC=O	1232.9	Standard polar	33892256
(Z)-4-Heptenal	CC\C=C/CCC=O	884.2	Standard non polar	33892256
(Z)-4-Heptenal	CC\C=C/CCC=O	907.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-4-Heptenal,1TMS,isomer #1	CC/C=C\CC=CO[Si](C)(C)C	1108.2	Semi standard non polar	33892256
(Z)-4-Heptenal,1TMS,isomer #1	CC/C=C\CC=CO[Si](C)(C)C	1058.9	Standard non polar	33892256
(Z)-4-Heptenal,1TBDMS,isomer #1	CC/C=C\CC=CO[Si](C)(C)C(C)(C)C	1333.3	Semi standard non polar	33892256
(Z)-4-Heptenal,1TBDMS,isomer #1	CC/C=C\CC=CO[Si](C)(C)C(C)(C)C	1294.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (Z)-4-Heptenal EI-B (Non-derivatized)	splash10-069u-9000000000-a21983533c6d768fcdeb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (Z)-4-Heptenal EI-B (Non-derivatized)	splash10-069u-9000000000-a21983533c6d768fcdeb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4-Heptenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-016u-9000000000-5d76234766167595db2b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-4-Heptenal 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 - (Z)-4-Heptenal 10V, Positive-QTOF	splash10-03di-5900000000-c4fc4e1ca06261747188	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 20V, Positive-QTOF	splash10-03dj-9300000000-617654f99de1be24ae18	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 40V, Positive-QTOF	splash10-052f-9000000000-82a9a5287591d3b02959	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 10V, Negative-QTOF	splash10-03di-1900000000-5cc68332e2c5838036ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 20V, Negative-QTOF	splash10-03di-4900000000-98926724feb85d968be9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 40V, Negative-QTOF	splash10-0006-9000000000-309b2b36e20f6efa162c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 10V, Positive-QTOF	splash10-067j-9000000000-74f7e39be12fe64dd9e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 20V, Positive-QTOF	splash10-066r-9000000000-6d554f02ccd1f3aa350c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 40V, Positive-QTOF	splash10-066r-9000000000-37fd3c1dc45c345e1a05	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 10V, Negative-QTOF	splash10-03di-0900000000-6e2ef191e20e94bd344c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 20V, Negative-QTOF	splash10-0006-9300000000-abb6df9eba9b1698307b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-4-Heptenal 40V, Negative-QTOF	splash10-0pbc-9000000000-1969e278506ca228958c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

Cytoplasm
Extracellular

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

FDB008061

KNApSAcK ID

Not Available

Chemspider ID

4515279

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5362814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027821

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 (Z)-4-Heptenal (HMDB0031483)

MOL for HMDB0031483 ((Z)-4-Heptenal)

3D MOL for HMDB0031483 ((Z)-4-Heptenal)

3D SDF for HMDB0031483 ((Z)-4-Heptenal)

3D-SDF for HMDB0031483 ((Z)-4-Heptenal)

PDB for HMDB0031483 ((Z)-4-Heptenal)

3D PDB for HMDB0031483 ((Z)-4-Heptenal)

SMILES for HMDB0031483 ((Z)-4-Heptenal)

INCHI for HMDB0031483 ((Z)-4-Heptenal)

Structure for HMDB0031483 ((Z)-4-Heptenal)

3D Structure for HMDB0031483 ((Z)-4-Heptenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra