Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:54:08 UTC

Update Date

2023-02-21 17:23:11 UTC

HMDB ID

HMDB0033167

Secondary Accession Numbers

HMDB33167

Metabolite Identification

Common Name

Ethyl cyclohexanecarboxylate

Description

Ethyl cyclohexanecarboxylate, also known as ethoxycarbonylcyclohexane or ethyl cyclohexylformate, belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Ethyl cyclohexanecarboxylate is a cheese, fruity, and winey tasting compound. Ethyl cyclohexanecarboxylate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Ethyl cyclohexanecarboxylate.

Structure

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

COMPND    HMDB0033167
HETATM    1  C1  UNL     1       3.873  -0.285  -0.237  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.209  -1.169   0.768  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.803  -1.182   0.656  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.029  -0.042   0.793  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.653   1.035   1.027  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.453  -0.061   0.674  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.045   1.309   0.864  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.236   1.544  -0.041  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.110   0.322  -0.167  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.348  -0.904  -0.598  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.868  -0.569  -0.672  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.218  -0.168  -1.109  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.079   0.698   0.268  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.845  -0.746  -0.515  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.546  -2.229   0.581  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.545  -0.912   1.802  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.865  -0.726   1.456  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.241   2.043   0.611  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.300   1.487   1.936  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.855   2.333   0.444  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.860   1.885  -1.026  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.853   0.543  -0.966  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.599   0.127   0.793  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.430  -1.713   0.180  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.690  -1.324  -1.548  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.731   0.210  -1.463  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.317  -1.506  -0.924  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   11   17
CONECT    7    8   18   19
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cyclohexanecarboxylic acid ethyl ester	ChEBI
Cyclohexanecarboxylic acid, ethyl ester	ChEBI
Ethoxycarbonylcyclohexane	ChEBI
Ethyl cyclohexanoate	ChEBI
Ethyl cyclohexanocarboxylate	ChEBI
Ethyl cyclohexylcarboxylate	ChEBI
Ethyl cyclohexylformate	ChEBI
Ethyl cyclohexylmethanoate	ChEBI
Ethyl hexahydrobenzoate	ChEBI
FEMA 3544	ChEBI
Cyclohexanecarboxylate ethyl ester	Generator
Cyclohexanecarboxylate, ethyl ester	Generator
Ethyl cyclohexanoic acid	Generator
Ethyl cyclohexanocarboxylic acid	Generator
Ethyl cyclohexylcarboxylic acid	Generator
Ethyl cyclohexylformic acid	Generator
Ethyl cyclohexylmethanoic acid	Generator
Ethyl hexahydrobenzoic acid	Generator
Ethyl cyclohexanecarboxylic acid	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

ethyl cyclohexanecarboxylate

Traditional Name

ethyl cyclohexanecarboxylate

CAS Registry Number

3289-28-9

SMILES

CCOC(=O)C1CCCCC1

InChI Identifier

InChI=1S/C9H16O2/c1-2-11-9(10)8-6-4-3-5-7-8/h8H,2-7H2,1H3

InChI Key

JJOYCHKVKWDMEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	82.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	150 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.757 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.83 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.39	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.36 m³·mol⁻¹	ChemAxon
Polarizability	18.28 Å³	ChemAxon
Number of Rings	1	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]+	136.125	31661259
DarkChem	[M-H]-	132.97	31661259
DeepCCS	[M+H]+	141.426	30932474
DeepCCS	[M-H]-	138.752	30932474
DeepCCS	[M-2H]-	175.122	30932474
DeepCCS	[M+Na]+	150.46	30932474
AllCCS	[M+H]+	135.9	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.9	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	141.7	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.	5.48 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4567 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2268.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	558.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	356.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	655.3 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	711.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	171.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1380.1 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	1426.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	562.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	530.3 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	61.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl cyclohexanecarboxylate	CCOC(=O)C1CCCCC1	1587.2	Standard polar	33892256
Ethyl cyclohexanecarboxylate	CCOC(=O)C1CCCCC1	1133.1	Standard non polar	33892256
Ethyl cyclohexanecarboxylate	CCOC(=O)C1CCCCC1	1146.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diarrhea-predominant IBS	23516449	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011176

KNApSAcK ID

Not Available

Chemspider ID

17646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18686

PDB ID

Not Available

ChEBI ID

88965

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1036791

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 Ethyl cyclohexanecarboxylate (HMDB0033167)

MOL for HMDB0033167 (Ethyl cyclohexanecarboxylate)

3D MOL for HMDB0033167 (Ethyl cyclohexanecarboxylate)

3D SDF for HMDB0033167 (Ethyl cyclohexanecarboxylate)

3D-SDF for HMDB0033167 (Ethyl cyclohexanecarboxylate)

PDB for HMDB0033167 (Ethyl cyclohexanecarboxylate)

3D PDB for HMDB0033167 (Ethyl cyclohexanecarboxylate)

SMILES for HMDB0033167 (Ethyl cyclohexanecarboxylate)

INCHI for HMDB0033167 (Ethyl cyclohexanecarboxylate)

Structure for HMDB0033167 (Ethyl cyclohexanecarboxylate)

3D Structure for HMDB0033167 (Ethyl cyclohexanecarboxylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized