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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-23 05:26:21 UTC

Update Date

2023-02-21 17:31:04 UTC

HMDB ID

HMDB0062666

Secondary Accession Numbers

HMDB62666

Metabolite Identification

Common Name

Triethylene Glycol Monomethyl Ether

Description

Triethylene Glycol Monomethyl Ether, also known as 3,6,9-trioxa-1-decanol or methoxytriethylene glycol, belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3). Triethylene Glycol Monomethyl Ether is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

COMPND    HMDB0062666
HETATM    1  C1  UNL     1       4.060   0.155   0.679  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.410   1.283   0.210  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.819   1.105  -1.017  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.782   0.008  -0.961  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.830   0.393  -0.023  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.190  -0.539   0.125  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.141   0.012   1.169  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.212  -0.802   1.430  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.979  -1.027   0.307  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.560   0.215  -0.306  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.306  -0.182  -1.426  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.445  -0.727   0.826  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.880  -0.092  -0.040  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.566   0.446   1.626  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.302   2.066  -1.279  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.557   0.943  -1.826  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.256  -0.954  -0.778  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.276  -0.092  -1.968  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.685  -0.601  -0.888  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.164  -1.541   0.357  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.425   1.043   0.831  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.538   0.126   2.097  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.831  -1.705   0.594  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.430  -1.575  -0.494  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.774   0.887  -0.686  1.00  0.00           H  
HETATM   26  H15 UNL     1      -4.159   0.761   0.434  1.00  0.00           H  
HETATM   27  H16 UNL     1      -5.116   0.390  -1.433  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9
CONECT    9   10   23   24
CONECT   10   11   25   26
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,6,9-Trioxa-1-decanol	ChEBI
Methoxytriethylene glycol	ChEBI
Methoxytriglycol	ChEBI
Methyl triethylene glycol	ChEBI
Methyltrioxitol	ChEBI
Triethylene glycolmonomethyl ether	ChEBI

Chemical Formula

C₇H₁₆O₄

Average Molecular Weight

164.1995

Monoisotopic Molecular Weight

164.104859

IUPAC Name

2-[2-(2-methoxyethoxy)ethoxy]ethan-1-ol

Traditional Name

methoxy triethylene glycol

CAS Registry Number

112-35-6

SMILES

COCCOCCOCCO

InChI Identifier

InChI=1S/C7H16O4/c1-9-4-5-11-7-6-10-3-2-8/h8H,2-7H2,1H3

InChI Key

JLGLQAWTXXGVEM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Polyethylene glycols

Alternative Parents

Substituents

Polyethylene glycol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hydroxypolyether (CHEBI:84233 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062666)

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	130 g/l	ALOGPS
LogP	-0.55	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.55	ALOGPS
logP	-0.66	ChemAxon
logS	-0.1	ALOGPS
pKa (Strongest Acidic)	15.12	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	41.39 m³·mol⁻¹	ChemAxon
Polarizability	18.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.141	31661259
DarkChem	[M-H]-	132.877	31661259
DeepCCS	[M+H]+	137.286	30932474
DeepCCS	[M-H]-	134.316	30932474
DeepCCS	[M-2H]-	170.832	30932474
DeepCCS	[M+Na]+	145.952	30932474
AllCCS	[M+H]+	137.4	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	140.8	32859911
AllCCS	[M+Na]+	141.8	32859911
AllCCS	[M-H]-	139.5	32859911
AllCCS	[M+Na-2H]-	141.8	32859911
AllCCS	[M+HCOO]-	144.3	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.	1.96 minutes	32390414
Predicted by Siyang on May 30, 2022	8.907 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1375.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	108.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	45.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	225.9 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	302.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	710.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	238.8 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	839.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	352.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	225.3 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	145.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triethylene Glycol Monomethyl Ether	COCCOCCOCCO	1968.8	Standard polar	33892256
Triethylene Glycol Monomethyl Ether	COCCOCCOCCO	1187.5	Standard non polar	33892256
Triethylene Glycol Monomethyl Ether	COCCOCCOCCO	1208.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Triethylene Glycol Monomethyl Ether,1TMS,isomer #1	COCCOCCOCCO[Si](C)(C)C	1361.6	Semi standard non polar	33892256
Triethylene Glycol Monomethyl Ether,1TBDMS,isomer #1	COCCOCCOCCO[Si](C)(C)C(C)(C)C	1576.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether EI-B (Non-derivatized)	splash10-0a4j-9000000000-562841fb0856c2a8cd69	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether EI-B (Non-derivatized)	splash10-0a4s-9000000000-4dd56e60ba4fd46d4c26	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether CI-B (Non-derivatized)	splash10-014i-1900000000-d8d9a7d9b09505c76950	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether EI-B (Non-derivatized)	splash10-0a4j-9000000000-562841fb0856c2a8cd69	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether EI-B (Non-derivatized)	splash10-0a4s-9000000000-4dd56e60ba4fd46d4c26	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Triethylene Glycol Monomethyl Ether CI-B (Non-derivatized)	splash10-014i-1900000000-d8d9a7d9b09505c76950	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol Monomethyl Ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-002s-9100000000-51e1ffd9b7fa1e775726	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol Monomethyl Ether GC-MS (1 TMS) - 70eV, Positive	splash10-0072-9600000000-71af7326ddcb247269b1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Triethylene Glycol Monomethyl Ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Triethylene Glycol Monomethyl Ether 10V, Positive-QTOF	splash10-014i-2900000000-42e7c0b43d669dfe658a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 20V, Positive-QTOF	splash10-066s-7900000000-b36e795fc3f3aa2ece10	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 40V, Positive-QTOF	splash10-052b-9000000000-0db1c7dbf3a715b9a937	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 10V, Negative-QTOF	splash10-03di-2900000000-30baec6dc9582d3882f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 20V, Negative-QTOF	splash10-03di-6900000000-1020c16cec3fdfa84895	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 40V, Negative-QTOF	splash10-06to-9200000000-4eab139a8076f768e9dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 10V, Negative-QTOF	splash10-0r00-9400000000-71f1a8044dd5b7579c1f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 20V, Negative-QTOF	splash10-0a4i-9200000000-97a14e8363358ff2fe35	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 40V, Negative-QTOF	splash10-0btc-9000000000-dc120bf5ee274d9889fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 10V, Positive-QTOF	splash10-006t-9000000000-92bae473cd57e3db6b48	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 20V, Positive-QTOF	splash10-052b-9000000000-eeba4ac8eb456e4fb6a3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Triethylene Glycol Monomethyl Ether 40V, Positive-QTOF	splash10-052b-9000000000-8bbbc9f225ae8894688d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8178

PDB ID

Not Available

ChEBI ID

84233

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

Not Available

Showing metabocard for Triethylene Glycol Monomethyl Ether (HMDB0062666)

MOL for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

3D MOL for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

3D SDF for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

3D-SDF for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

PDB for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

3D PDB for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

SMILES for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

INCHI for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

Structure for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

3D Structure for HMDB0062666 (Triethylene Glycol Monomethyl Ether)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra