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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:03 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037025

Secondary Accession Numbers

HMDB37025

Metabolite Identification

Common Name

Hop ether

Description

Hop ether belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Hop ether has been detected, but not quantified in, alcoholic beverages and fats and oils. This could make HOP ether a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Hop ether.

Structure

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

COMPND    HMDB0037025
HETATM    1  C1  UNL     1       3.145   0.703   0.428  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.071   0.181  -0.098  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.959  -1.235  -0.562  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.475  -1.501  -0.288  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.206  -0.227  -0.726  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.756   0.846  -0.349  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.155   1.415   0.910  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.895   0.608   1.272  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.435   0.046   0.136  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.344   1.048  -0.561  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.219  -1.197   0.394  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.038   0.109   0.556  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.213   1.738   0.762  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.608  -1.909   0.029  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.212  -1.357  -1.616  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.111  -2.398  -0.784  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.392  -1.534   0.827  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.527  -0.231  -1.767  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.919   1.597  -1.139  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.245   2.425   0.659  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.914   1.500   1.689  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.414   0.821  -0.311  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.200   1.012  -1.657  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.153   2.082  -0.227  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.733  -1.473  -0.563  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.623  -2.065   0.688  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.976  -1.004   1.159  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    6
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6    9   18
CONECT    6    7   19
CONECT    7    8   20   21
CONECT    8    9
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2-Dimethyl-6-methylene-3-oxabicyclo[3.3.0]octane	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1,1-dimethyl-4-methylidene-hexahydro-1H-cyclopenta[c]furan

Traditional Name

1,1-dimethyl-4-methylidene-tetrahydro-3H-cyclopenta[c]furan

CAS Registry Number

19901-95-2

SMILES

CC1(C)OCC2C1CCC2=C

InChI Identifier

InChI=1S/C10H16O/c1-7-4-5-9-8(7)6-11-10(9,2)3/h8-9H,1,4-6H2,2-3H3

InChI Key

PSYUARCNIZCTFI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037025)

Source

Endogenous

Endogenous (HMDB: HMDB0037025)

Exogenous

Food

Food (HMDB: HMDB0037025)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0037025)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037025)

Role

Biological role

Energy source (HMDB: HMDB0037025)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037025)

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	170.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	2.35	ALOGPS
logP	1.88	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.68 m³·mol⁻¹	ChemAxon
Polarizability	17.8 Å³	ChemAxon
Number of Rings	2	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]+	134.244	31661259
DarkChem	[M-H]-	131.167	31661259
DeepCCS	[M+H]+	135.514	30932474
DeepCCS	[M-H]-	132.618	30932474
DeepCCS	[M-2H]-	169.397	30932474
DeepCCS	[M+Na]+	144.679	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.4	32859911
AllCCS	[M+Na]+	136.6	32859911
AllCCS	[M-H]-	137.1	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.7	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.	4.05 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5679 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2146.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	547.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	320.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	162.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	620.8 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	750.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	148.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1207.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.3 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	1286.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	513.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	540.2 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	22.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hop ether	CC1(C)OCC2C1CCC2=C	1341.7	Standard polar	33892256
Hop ether	CC1(C)OCC2C1CCC2=C	1044.5	Standard non polar	33892256
Hop ether	CC1(C)OCC2C1CCC2=C	1071.7	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 - Hop ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-9400000000-5eabdd67f1ca766cb99f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hop ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hop 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 - Hop ether 10V, Positive-QTOF	splash10-0udi-0900000000-11646b70c1d2a10ef4ae	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 20V, Positive-QTOF	splash10-0udi-5900000000-a8491136c892478cc7c9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 40V, Positive-QTOF	splash10-0zfr-9100000000-0e2d002b6f49ce05ed97	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 10V, Negative-QTOF	splash10-0udi-0900000000-9fffe29d679e6b3e191b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 20V, Negative-QTOF	splash10-0udi-0900000000-b2f79cdd5893a0c3fa49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 40V, Negative-QTOF	splash10-01di-6900000000-6871771286580f0c040b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 10V, Positive-QTOF	splash10-0udi-1900000000-0900ac9b99edbc71d070	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 20V, Positive-QTOF	splash10-0il4-9800000000-5a0c6ea6c61bbb8b7287	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 40V, Positive-QTOF	splash10-0006-9200000000-42796e14c3b02c59fe12	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 20V, Negative-QTOF	splash10-0udi-2900000000-7e97279d665245887438	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hop ether 40V, Negative-QTOF	splash10-05bp-5900000000-71fc5b0df04893aaa40f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB016005

KNApSAcK ID

C00055915

Chemspider ID

483800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

556518

PDB ID

Not Available

ChEBI ID

171943

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1633731

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 Hop ether (HMDB0037025)

MOL for HMDB0037025 (Hop ether)

3D MOL for HMDB0037025 (Hop ether)

3D SDF for HMDB0037025 (Hop ether)

3D-SDF for HMDB0037025 (Hop ether)

PDB for HMDB0037025 (Hop ether)

3D PDB for HMDB0037025 (Hop ether)

SMILES for HMDB0037025 (Hop ether)

INCHI for HMDB0037025 (Hop ether)

Structure for HMDB0037025 (Hop ether)

3D Structure for HMDB0037025 (Hop ether)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra