MiMeDB: Showing metabocard for Citral (MMDBc0033609)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:43 UTC

Update Date

2022-08-31 22:37:01 UTC

Metabolite ID

MMDBc0033609

Metabolite Identification

Common Name

Citral

Description

Citral, also known as geranial, 3,7-dimethyl-2,6-octadienal, or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as citral or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID:6991645 , 26657499 ). Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID:28974979 ) and pheromonal effects in nematodes and insects (PMID:26973536 ). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke).

Structure

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

COMPND    HMDB0035078
HETATM    1  C1  UNL     1      -2.434   1.355   0.221  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.595  -0.016  -0.306  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.852  -0.435  -0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.609  -0.883  -0.200  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.346  -0.446   0.457  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.750  -0.611  -0.596  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.056  -0.195  -0.019  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.551  -0.912   1.161  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.751   0.779  -0.538  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.041   1.217   0.004  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.686   2.159  -0.519  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.348   1.972   0.082  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.556   1.821  -0.303  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.208   1.405   1.298  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.686  -1.174  -1.784  1.00  0.00           H  
HETATM   16  H5  UNL     1      -4.538  -0.954  -0.241  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.418   0.401  -1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.722  -1.899  -0.588  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.410   0.589   0.831  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.151  -1.172   1.287  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.471  -0.034  -1.481  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.736  -1.690  -0.868  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.078  -1.909   1.239  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.237  -0.329   2.068  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.650  -1.081   1.154  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.371   1.286  -1.395  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.497   0.754   0.874  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   11   27
END

Synonyms

Value	Source
(2E)-Geranial	ChEBI
(e)-Citral	ChEBI
(e)-Geranial	ChEBI
alpha-Citral	ChEBI
Citral a	ChEBI
Lemonal	ChEBI
trans-Citral	ChEBI
a-Citral	Generator
Α-citral	Generator
(2E)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethylocta-2,6-dienal	HMDB
3,7-Dimethyl-(2E)-2,6-octadienal	HMDB
3,7-Dimethyl-(e)-2,6-octadienal	HMDB
3,7-Dimethyl-trans-2,6-octadienal	HMDB
alpha -Citral	HMDB
beta-Geranial	HMDB
Citral-a	HMDB
Genanial	HMDB
Geranal	HMDB
trans-3,7-Dimethyl-2,6-octadienal	HMDB
(Z)-Citral	MeSH, HMDB
Citral	MeSH, HMDB
(2E)-3,7-Dimethyl-2,6-octadien-1-al	HMDB
(E)-3,7-Dimethyl-2,6-octadienal	HMDB
(E)-Neral	HMDB
Geranaldehyde	HMDB
Geranial	HMDB
beta-Neral	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-al	HMDB
trans-Geranial	HMDB
β-Geranial	HMDB
β-Neral	HMDB
3,7-Dimethyl-2,6-octadien-1-al	HMDB
3,7-Dimethyl-2,6-octadienal	HMDB

Molecular Formula

C₁₀H₁₆O

Average Mass

152.237

Monoisotopic Mass

152.120115135

IUPAC Name

(2E)-3,7-dimethylocta-2,6-dienal

Traditional Name

α-citral

CAS Registry Number

5392-40-5

SMILES

CC(C)=CCC\C(C)=C\C=O

InChI Identifier

InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+

InChI Key

WTEVQBCEXWBHNA-JXMROGBWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:16980 )
monoterpenoid (CHEBI:16980 )
Acyclic monoterpenoids (C01499 )
Linear monoterpenes (C01499 )
Acyclic monoterpenoids (LMPR0102010003 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	3.37	ALOGPS
logP	2.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.1	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	50.12 m³·mol⁻¹	ChemAxon
Polarizability	18.6 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown
Bacteria/NULL	Proteobacteria	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20809147
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258

External Links

HMDB ID

HMDB0035078

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Citral

METLIN ID

Not Available

PubChem Compound

638011

PDB ID

Not Available

ChEBI ID

16980

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Duarte MC, Figueira GM, Sartoratto A, Rehder VL, Delarmelina C: Anti-Candida activity of Brazilian medicinal plants. J Ethnopharmacol. 2005 Feb 28;97(2):305-11. doi: 10.1016/j.jep.2004.11.016. Epub 2005 Jan 5. [PubMed:15707770 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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..
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Citral (MMDBc0033609)

MOL for #<Metabolite:0x0000560bdf4f8c88>

3D MOL for #<Metabolite:0x0000560bdf4f8c88>

3D SDF for #<Metabolite:0x0000560bdf4f8c88>

3D-SDF for #<Metabolite:0x0000560bdf4f8c88>

PDB for #<Metabolite:0x0000560bdf4f8c88>

3D PDB for #<Metabolite:0x0000560bdf4f8c88>

SMILES for #<Metabolite:0x0000560bdf4f8c88>

INCHI for #<Metabolite:0x0000560bdf4f8c88>

Structure for #<Metabolite:0x0000560bdf4f8c88>

3D Structure for #<Metabolite:0x0000560bdf4f8c88>