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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:36 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036092

Secondary Accession Numbers

HMDB36092

Metabolite Identification

Common Name

exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol

Description

exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol, 9ci	HMDB
exo-Form	HMDB

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-ol

Traditional Name

2-methyl-3-methylidenebicyclo[2.2.1]heptan-2-ol

CAS Registry Number

59300-40-2

SMILES

CC1(O)C2CCC(C2)C1=C

InChI Identifier

InChI=1S/C9H14O/c1-6-7-3-4-8(5-7)9(6,2)10/h7-8,10H,1,3-5H2,2H3

InChI Key

RZEAOYIZHBELOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036092)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036092)

Source

Endogenous

Endogenous (HMDB: HMDB0036092)

Plant

Poaceae (HMDB: HMDB0036092)

Animal

Animal (HMDB: HMDB0036092)

Exogenous

Food

Food (HMDB: HMDB0036092)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036092)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036092)

Cellular process

Cell signaling (HMDB: HMDB0036092)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036092)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036092)

Nutrient

Nutrient (HMDB: HMDB0036092)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036092)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0036092)

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	2501 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	4.22 g/L	ALOGPS
logP	2.32	ALOGPS
logP	1.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	19.15	ChemAxon
pKa (Strongest Basic)	-0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.7 m³·mol⁻¹	ChemAxon
Polarizability	15.96 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]+	129.453	31661259
DarkChem	[M-H]-	125.531	31661259
DeepCCS	[M+H]+	131.352	30932474
DeepCCS	[M-H]-	127.628	30932474
DeepCCS	[M-2H]-	164.997	30932474
DeepCCS	[M+Na]+	140.305	30932474
AllCCS	[M+H]+	129.4	32859911
AllCCS	[M+H-H2O]+	124.8	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	131.0	32859911
AllCCS	[M+Na-2H]-	132.5	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol	CC1(O)C2CCC(C2)C1=C	1596.9	Standard polar	33892256
exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol	CC1(O)C2CCC(C2)C1=C	1046.3	Standard non polar	33892256
exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol	CC1(O)C2CCC(C2)C1=C	1071.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol,1TMS,isomer #1	C=C1C2CCC(C2)C1(C)O[Si](C)(C)C	1170.8	Semi standard non polar	33892256
exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol,1TBDMS,isomer #1	C=C1C2CCC(C2)C1(C)O[Si](C)(C)C(C)(C)C	1405.9	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 - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9400000000-5222b41fa0094e1f7ca9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00rg-9400000000-5adb8d4ba42512441a90	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 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 - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 10V, Positive-QTOF	splash10-00dr-0900000000-53c8f90a24422ff1de4d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 20V, Positive-QTOF	splash10-00dr-3900000000-6535d49012760cae146a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 40V, Positive-QTOF	splash10-014i-9200000000-56803ec17eafe8d5defc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 10V, Negative-QTOF	splash10-000i-0900000000-cf99887a64244167e403	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 20V, Negative-QTOF	splash10-000i-0900000000-6ab4e5289e2c43f57059	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 40V, Negative-QTOF	splash10-00du-6900000000-515ae74df8e08cb06a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 20V, Negative-QTOF	splash10-000i-1900000000-620ebf95494fb9a3d34c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 40V, Negative-QTOF	splash10-014u-4900000000-aba5c80d943d99ed7bb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 10V, Positive-QTOF	splash10-00di-5900000000-857e7b5cd5a6363b892a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 20V, Positive-QTOF	splash10-006y-9300000000-84541b5b1e8887f62017	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol 40V, Positive-QTOF	splash10-0006-9300000000-e571fcf8ad7fd83e634b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

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

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

FDB014932

KNApSAcK ID

Not Available

Chemspider ID

35014092

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67760064

PDB ID

Not Available

ChEBI ID

169123

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853571

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Schmitz G, Braun V: Cell-bound and secreted proteases of Serratia marcescens. J Bacteriol. 1985 Mar;161(3):1002-9. [PubMed:2579058 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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. 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. 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) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. 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 exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol (HMDB0036092)

MOL for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

3D MOL for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

3D SDF for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

3D-SDF for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

PDB for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

3D PDB for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

SMILES for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

INCHI for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

Structure for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

3D Structure for HMDB0036092 (exo-2-Methyl-3-methylenebicyclo[2.2.1]heptan-2-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra