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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:03:54 UTC

Update Date

2021-09-26 22:53:04 UTC

HMDB ID

HMDB0244945

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-(Hexyloxy)ethanol

Description

2-(Hexyloxy)ethanol, also known as EGHE, belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. Based on a literature review very few articles have been published on 2-(Hexyloxy)ethanol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-(hexyloxy)ethanol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-(Hexyloxy)ethanol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

COMPND    HMDB0244945
HETATM    1  C1  UNL     1       3.898  -0.768  -0.714  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.995   0.388  -0.406  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.778  -0.069   0.412  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.947   1.156   0.664  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.302   0.857   1.475  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.184  -0.142   0.754  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.528   0.421  -0.459  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.344  -0.392  -1.232  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.645  -0.724  -0.557  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.312   0.465  -0.310  1.00  0.00           O  
HETATM   11  H1  UNL     1       4.172  -0.757  -1.805  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.838  -0.744  -0.126  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.434  -1.758  -0.500  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.549   1.161   0.159  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.640   0.858  -1.363  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.149  -0.561   1.315  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.163  -0.762  -0.227  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.695   1.595  -0.312  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.552   1.859   1.277  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.044   0.440   2.469  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.911   1.784   1.571  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.068  -0.293   1.420  1.00  0.00           H  
HETATM   23  H13 UNL     1      -0.620  -1.091   0.680  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.604   0.211  -2.144  1.00  0.00           H  
HETATM   25  H15 UNL     1      -1.845  -1.298  -1.605  1.00  0.00           H  
HETATM   26  H16 UNL     1      -3.552  -1.380   0.308  1.00  0.00           H  
HETATM   27  H17 UNL     1      -4.262  -1.279  -1.313  1.00  0.00           H  
HETATM   28  H18 UNL     1      -4.589   0.824  -1.210  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
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
EGHE	HMDB
Ethylene glycol monohexyl ether	HMDB

Chemical Formula

C₈H₁₈O₂

Average Molecular Weight

146.23

Monoisotopic Molecular Weight

146.13067982

IUPAC Name

2-(hexyloxy)ethan-1-ol

Traditional Name

ethanol, 2-(hexyloxy)-

CAS Registry Number

Not Available

SMILES

CCCCCCOCCO

InChI Identifier

InChI=1S/C8H18O2/c1-2-3-4-5-7-10-8-6-9/h9H,2-8H2,1H3

InChI Key

UPGSWASWQBLSKZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Dialkyl ethers

Alternative Parents

Substituents

Dialkyl ether
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.82	ALOGPS
logP	1.65	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	15.12	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	42.38 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	138.813	30932474
DeepCCS	[M-H]-	135.761	30932474
DeepCCS	[M-2H]-	172.286	30932474
DeepCCS	[M+Na]+	147.454	30932474
AllCCS	[M+H]+	135.0	32859911
AllCCS	[M+H-H2O]+	131.1	32859911
AllCCS	[M+NH4]+	138.7	32859911
AllCCS	[M+Na]+	139.8	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	140.5	32859911
AllCCS	[M+HCOO]-	143.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.8741 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1869.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	350.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	501.2 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	536.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1049.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	366.1 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	1216.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	389.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	318.5 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	42.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(Hexyloxy)ethanol	CCCCCCOCCO	1591.3	Standard polar	33892256
2-(Hexyloxy)ethanol	CCCCCCOCCO	1101.1	Standard non polar	33892256
2-(Hexyloxy)ethanol	CCCCCCOCCO	1117.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hexyloxy)ethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-005d-9100000000-7c3f081d0c8016e6c4df	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hexyloxy)ethanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hexyloxy)ethanol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(Hexyloxy)ethanol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 2-(Hexyloxy)ethanol 10V, Positive-QTOF	splash10-0002-2900000000-1e98a39501f2ab4d9c60	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 20V, Positive-QTOF	splash10-000j-9400000000-d23cfd16da0d6d14243c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 40V, Positive-QTOF	splash10-052p-9000000000-1291be81dfe884177bb7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 10V, Negative-QTOF	splash10-0002-2900000000-0031c19d401419e783dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 20V, Negative-QTOF	splash10-0002-8900000000-6cfe7f452976f56798b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 40V, Negative-QTOF	splash10-01ox-9000000000-293864c011a48e00e7e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 10V, Positive-QTOF	splash10-0002-9000000000-4ba48878f1847fb51d7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 20V, Positive-QTOF	splash10-0a4m-9000000000-803cd68c399ce25884dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 40V, Positive-QTOF	splash10-052g-9000000000-96d5cfbb99ae857043d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 10V, Negative-QTOF	splash10-0udj-2900000000-681245f09f16d03d6787	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 20V, Negative-QTOF	splash10-0bt9-9000000000-65fa5fb526bac18f2d35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(Hexyloxy)ethanol 40V, Negative-QTOF	splash10-0a4l-9000000000-433d9760215dc4382190	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8170

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2-(Hexyloxy)ethanol (HMDB0244945)

MOL for HMDB0244945 (2-(Hexyloxy)ethanol)

3D MOL for HMDB0244945 (2-(Hexyloxy)ethanol)

3D SDF for HMDB0244945 (2-(Hexyloxy)ethanol)

3D-SDF for HMDB0244945 (2-(Hexyloxy)ethanol)

PDB for HMDB0244945 (2-(Hexyloxy)ethanol)

3D PDB for HMDB0244945 (2-(Hexyloxy)ethanol)

SMILES for HMDB0244945 (2-(Hexyloxy)ethanol)

INCHI for HMDB0244945 (2-(Hexyloxy)ethanol)

Structure for HMDB0244945 (2-(Hexyloxy)ethanol)

3D Structure for HMDB0244945 (2-(Hexyloxy)ethanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra