MiMeDB: Showing metabocard for Heptenal (MMDBc0033648)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:23 UTC

Update Date

2024-04-30 20:14:35 UTC

Metabolite ID

MMDBc0033648

Metabolite Identification

Common Name

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

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

Molecular Formula

C₇H₁₂O

Average Mass

112.1696

Monoisotopic Mass

112.088815006

IUPAC Name

(2E)-hept-2-enal

Traditional Name

2-heptenal, (2E)-

CAS Registry Number

29381-66-6

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6u-9000000000-1e3da23b690c3ef7c024	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-9000000000-5dedb721b6e6ec596371	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-6900000000-4a2743833647b0bdb535	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-9400000000-6ff3124de5daea2c5dc7	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-9000000000-21a1a7ea291def5b6e29	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-316d71b866cb472295ff	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-4900000000-af5169f2777e09a2d955	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-144150625b2c04635793	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-914db82f697f24d29d0c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-ac71f7a8d0b92d89ca07	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0rkc-9000000000-de34104ae53e4248a8d1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-8d02e35f9ff6d556c0bb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066u-9000000000-aa11d319dd6879fab78a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0673-9000000000-46f63dfa7a32f461d5ac	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-054o-9000000000-78a71f46d13bfca3d317	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit	Rubus	FooDB	31437929
Plant	Fruit	Solanum lycopersicum	FooDB	31437929
Plant	Calyx	Hibiscus sabdariffa	FooDB	31437929
Plant	Fruit	Cucumis sativus	FooDB	31437929
Plant	Fruit	Citrullus lanatus	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant	Bud	Carthamus tinctorius	FooDB	31437929
Plant	Seed	Vitis vinifera	FooDB	31437929
Plant	Leaves	Carthamus tinctorius	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.49	0.15	uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	0.16	0.05	uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Saliva	Detected but not Quantified				Adult (>18 years old)	Not Specified	Normal	HMDB	24421258

External Links

HMDB ID

HMDB0033827

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

References

Synthesis Reference

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). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Heptenal (MMDBc0033648)

MOL for #<Metabolite:0x00007fd0f800d450>

3D MOL for #<Metabolite:0x00007fd0f800d450>

3D SDF for #<Metabolite:0x00007fd0f800d450>

3D-SDF for #<Metabolite:0x00007fd0f800d450>

PDB for #<Metabolite:0x00007fd0f800d450>

3D PDB for #<Metabolite:0x00007fd0f800d450>

SMILES for #<Metabolite:0x00007fd0f800d450>

INCHI for #<Metabolite:0x00007fd0f800d450>

Structure for #<Metabolite:0x00007fd0f800d450>

3D Structure for #<Metabolite:0x00007fd0f800d450>