MiMeDB: Showing metabocard for Nonanal (MMDBc0047732)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:40:07 UTC

Update Date

2024-04-30 20:29:10 UTC

Metabolite ID

MMDBc0047732

Metabolite Identification

Common Name

Nonanal

Description

Nonanal, also known as nonyl aldehyde or pelargonaldehyde, 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. Thus, nonanal is considered to be a fatty aldehyde lipid molecule. Nonanal acts synergistically with carbon dioxide in that regard. Nonanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, ranging from yeast to humans. Nonanal is an aldehydic, citrus, and fat tasting compound. nonanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and gingers and in a lower concentration in sweet oranges, carrots, and limes. nonanal has also been detected, but not quantified, in several different foods, such as olives, cereals and cereal products, chinese cinnamons, common grapes, and oats. This could make nonanal a potential biomarker for the consumption of these foods. Nonanal has been identified as a compound that attracts Culex mosquitoes. Nonanal is a potentially toxic compound. Nonanal has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, autism, crohn's disease, and ulcerative colitis; also nonanal has been linked to the inborn metabolic disorders including celiac disease. Nonanal, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an alkyl aldehyde. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene. A colourless, oily liquid, nonanal is a component of perfumes.

Structure

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

COMPND    HMDB0059835
HETATM    1  C1  UNL     1      -3.332  -0.369  -0.596  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.018  -0.999  -0.219  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.413  -0.384   1.026  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.138   1.059   0.905  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.255   1.565  -0.154  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.153   1.178  -0.247  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.526  -0.239  -0.458  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.075  -0.254  -0.554  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.550  -1.630  -0.767  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.788  -2.571  -0.846  1.00  0.00           O  
HETATM   11  H1  UNL     1      -3.628   0.411   0.135  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.124  -1.132  -0.752  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.222   0.159  -1.575  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.208  -2.078  -0.010  1.00  0.00           H  
HETATM   15  H5  UNL     1      -1.322  -0.952  -1.080  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.652  -1.020   1.447  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.270  -0.458   1.804  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.650   1.363   1.896  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.124   1.603   0.936  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.260   2.706  -0.047  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.703   1.437  -1.189  1.00  0.00           H  
HETATM   22  H12 UNL     1       1.685   1.569   0.686  1.00  0.00           H  
HETATM   23  H13 UNL     1       1.620   1.832  -1.053  1.00  0.00           H  
HETATM   24  H14 UNL     1       1.178  -0.682  -1.390  1.00  0.00           H  
HETATM   25  H15 UNL     1       1.286  -0.852   0.409  1.00  0.00           H  
HETATM   26  H16 UNL     1       3.410   0.371  -1.401  1.00  0.00           H  
HETATM   27  H17 UNL     1       3.438   0.192   0.383  1.00  0.00           H  
HETATM   28  H18 UNL     1       4.610  -1.824  -0.857  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   10   28
END

Synonyms

Value	Source
N-Nonaldehyde	ChEBI
Nonanoic aldehyde	ChEBI
Nonyl aldehyde	ChEBI
Nonylaldehyde	ChEBI
Nonylic aldehyde	ChEBI
Pelargonaldehyde	ChEBI
Pelargonic aldehyde	ChEBI
N-Nonylaldehyde	HMDB
Nonanal	MeSH

Molecular Formula

C₉H₁₈O

Average Mass

142.2386

Monoisotopic Mass

142.135765198

IUPAC Name

nonanal

Traditional Name

nonanal

CAS Registry Number

Not Available

SMILES

CCCCCCCCC=O

InChI Identifier

InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3

InChI Key

GYHFUZHODSMOHU-UHFFFAOYSA-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

fatty aldehyde (CHEBI:84268 )
Fatty aldehydes (LMFA06000040 )
an <i>n</i>-alkanal (CPD-8491 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	3.81	ALOGPS
logP	2.99	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-6.9	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	7	ChemAxon
Refractivity	43.95 m³·mol⁻¹	ChemAxon
Polarizability	18.54 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)	splash10-052f-9000000000-7bfee629e196af9e810a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-7a91b8574f3d51d4856a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-373d544eb5629e680bc4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-858f5f7c138a343dc472	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-6653261e95803e235236	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-7bfee629e196af9e810a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-7a91b8574f3d51d4856a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-373d544eb5629e680bc4	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-858f5f7c138a343dc472	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4l-9000000000-6653261e95803e235236	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-062l-9000000000-b8472e31e5bcec84f30c	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	splash10-0006-1900000000-f0ef344b71801c87bae2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9700000000-6646461d0ed7f00c9732	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-e9cf39f812a5e37b3253	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-f0a7779f3ceded55079f	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2900000000-8a94df0d859760c12b51	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-c476311d08e1bd1d53df	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-31a4c0b614cfbc7c3156	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-fc1333865a778fe31452	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3e15d73ab7b0a83b0b4d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-9000000000-15622cc20ddbb14ed88c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-bacbd1e7d4f6be160b21	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-796b68d98dc297622b77	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-945f6bb4a733637d5cf8	2014-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2014-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-10-20	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0017812	Adenosine triphosphate	Adenosine monophosphate	Carboxylic acid reductase	Reduction	RHEA	34755880
MMDBr0017813	Adenosine triphosphate	Adenosine monophosphate	Carboxylic acid reductase	Reduction	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Celiac disease	Slight Decrease	Association	Human Feces	HMDB	21970810
Uremia	Slight Increase	Association	Human Blood	HMDB	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Food			FooDB	31437929
Plant	Shoot		FooDB	31437929
Plant	Fruit	Carica papaya	FooDB	31437929
Plant	Fruit	Olea europaea	FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant	Fruit	Coriandrum sativum	FooDB	31437929
Plant	Seed	Anethum graveolens	FooDB	31437929
Plant	Calyx	Hibiscus sabdariffa	FooDB	31437929
Plant	Fruit	Cucumis sativus	FooDB	31437929
Plant	Fruit	Citrus aurantiifolia	FooDB	31437929
Plant	Fruit	Citrus sinensis	FooDB	31437929
Plant	Seed	Sesamum orientale	FooDB	31437929
Plant		Apium graveolens var. dulce	FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant	Shoot	Camellia sinensis	FooDB	31437929
Plant	Bean	Phaseolus vulgaris	FooDB	31437929
Plant	Fruit	Citrullus lanatus	FooDB	31437929
Plant	Fruit	Citrus reticulata	FooDB	31437929
Plant	Oil	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Fruit	Prunus avium	FooDB	31437929
Plant	Juice	Rubus	FooDB	31437929
Plant	Plant	Ocimum basilicum	FooDB	31437929
Plant	Fruit juice	Vaccinium myrtillus	FooDB	31437929
Plant	Bark	Cinnamomum verum	FooDB	31437929
Plant	Plant	Cinnamomum aromaticum	FooDB	31437929
Plant		Apium graveolens var. rapaceum	FooDB	31437929
Plant		Brassica oleracea var. botrytis	FooDB	31437929
Plant	Fruit	Pyrus communis	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Seed	Vitis vinifera	FooDB	31437929
Plant	Fruit	Prunus avium	FooDB	31437929
Plant	Fruit	Prunus avium	FooDB	31437929
Plant	Seed	Carum carvi	FooDB	31437929
Plant	Steam volatile oil	Brassica oleracea var. italica	FooDB	31437929
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant	Fruit	Cucumis melo	FooDB	31437929
Plant	Shoot	Mentha spicata	FooDB	31437929
Plant	Flower	Carthamus tinctorius	FooDB	31437929
Plant	Fruit essential oil	Tamarindus indica	FooDB	31437929
Plant	Plant	Origanum vulgare	FooDB	31437929
Plant	Leaves	Carthamus tinctorius	FooDB	31437929
Plant	Essence	Cucumis sativus	FooDB	31437929
Plant	Rhizome	Zingiber officinale	FooDB	31437929
Plant	Fruit	Rubus	FooDB	31437929
Plant	Fruit	Psidium guajava	FooDB	31437929
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Shoot		FooDB	31437929
Plant	Fruit	Prunus avium	FooDB	31437929
Plant	Shoot		FooDB	31437929
Plant	Root oil	Daucus carota ssp. sativus	FooDB	31437929
Plant	Essential oil	Citrus limon	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929
Plant	Essential oil	Coriandrum sativum	FooDB	31437929
Plant	Root	Daucus carota	FooDB	31437929
Plant	Essential oil	Mentha spicata	FooDB	31437929
Plant	Root	Zingiber officinale	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected and Quantified			0	175854.749	nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	HMDB	21970810
Human Blood	Detected and Quantified	0.48	0.19			uM	Adult (>18 years old)	Both	uremia	HMDB	22626821
Human Blood	Detected and Quantified	0.26	0.16			uM	Adult (>18 years old)	Both	Normal	HMDB	22626821
Human Feces	Detected and Quantified			4874.439	470453.637	nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	HMDB	21970810
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Saliva	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	24657864
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified						Newborn (0-30 days old)	Both	Normal	HMDB	21386183
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	23454028
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	24130822
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24922509
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	26806034

External Links

HMDB ID

HMDB0059835

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003303

KNApSAcK ID

C00030828

Chemspider ID

29029

KEGG Compound ID

Not Available

BioCyc ID

CPD-8491

BiGG ID

Not Available

Wikipedia Link

Nonanal

METLIN ID

Not Available

PubChem Compound

31289

PDB ID

Not Available

ChEBI ID

84268

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 ]

Showing metabocard for Nonanal (MMDBc0047732)

MOL for #<Metabolite:0x000055e8c90285c0>

3D MOL for #<Metabolite:0x000055e8c90285c0>

3D SDF for #<Metabolite:0x000055e8c90285c0>

3D-SDF for #<Metabolite:0x000055e8c90285c0>

PDB for #<Metabolite:0x000055e8c90285c0>

3D PDB for #<Metabolite:0x000055e8c90285c0>

SMILES for #<Metabolite:0x000055e8c90285c0>

INCHI for #<Metabolite:0x000055e8c90285c0>

Structure for #<Metabolite:0x000055e8c90285c0>

3D Structure for #<Metabolite:0x000055e8c90285c0>