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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 20:38:10 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035625

Secondary Accession Numbers

HMDB35625

Metabolite Identification

Common Name

(-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane

Description

(-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 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 (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Fenchene	HMDB

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.234

Monoisotopic Molecular Weight

136.125200512

IUPAC Name

7,7-dimethyl-2-methylidenebicyclo[2.2.1]heptane

Traditional Name

7,7-dimethyl-2-methylidenebicyclo[2.2.1]heptane

CAS Registry Number

7378-37-2

SMILES

CC1(C)C2CCC1C(=C)C2

InChI Identifier

InChI=1S/C10H16/c1-7-6-8-4-5-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3

InChI Key

XCPQUQHBVVXMRQ-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
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a small molecule (CPD-12222 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035625)

Source

Endogenous

Endogenous (HMDB: HMDB0035625)

Plant

Plant (HMDB: HMDB0035625)

Animal

Animal (HMDB: HMDB0035625)

Exogenous

Food

Food (HMDB: HMDB0035625)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0035625)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035625)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035625)

Lipid metabolism pathway (HMDB: HMDB0035625)

Cellular process

Cell signaling (HMDB: HMDB0035625)

Biochemical process

Lipid transport (HMDB: HMDB0035625)

Role

Biological role

Energy source (HMDB: HMDB0035625)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035625)

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
Water Solubility	0.064 g/L	ALOGPS
logP	4.05	ALOGPS
logP	2.86	ChemAxon
logS	-3.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.65 m³·mol⁻¹	ChemAxon
Polarizability	17.05 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]+	130.931	31661259
DarkChem	[M-H]-	126.221	31661259
DeepCCS	[M+H]+	137.54	30932474
DeepCCS	[M-H]-	134.694	30932474
DeepCCS	[M-2H]-	171.471	30932474
DeepCCS	[M+Na]+	146.676	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	131.8	32859911
AllCCS	[M+Na-2H]-	133.2	32859911
AllCCS	[M+HCOO]-	134.9	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.	4.93 minutes	32390414
Predicted by Siyang on May 30, 2022	17.2764 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.76 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2127.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	660.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	238.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	397.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	604.6 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	795.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	294.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1313.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	439.8 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	1429.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	568.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	605.6 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	28.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane	CC1(C)C2CCC1C(=C)C2	1068.0	Standard polar	33892256
(-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane	CC1(C)C2CCC1C(=C)C2	931.2	Standard non polar	33892256
(-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane	CC1(C)C2CCC1C(=C)C2	931.4	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 - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g1-9800000000-7631ba227ff66a9a8ac9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 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 - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 10V, Positive-QTOF	splash10-000i-0900000000-cb7e9b81dbb4c230580f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 20V, Positive-QTOF	splash10-000i-0900000000-d3a6e3dbdc4aeddddbbf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 40V, Positive-QTOF	splash10-0kfy-9300000000-1b71cdf0e9a22815f156	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 10V, Negative-QTOF	splash10-000i-0900000000-d89294cca561202a2510	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 20V, Negative-QTOF	splash10-000i-0900000000-d89294cca561202a2510	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 40V, Negative-QTOF	splash10-014r-1900000000-77a8a686c49d19c68563	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 10V, Negative-QTOF	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 20V, Negative-QTOF	splash10-000i-0900000000-a013b4ae27f975ab5621	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 40V, Negative-QTOF	splash10-014r-0900000000-e6a62870045360b70d6d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 10V, Positive-QTOF	splash10-000i-0900000000-69bcafa7f6308517cec9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 20V, Positive-QTOF	splash10-054x-9300000000-57c5da55f9a095219277	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane 40V, Positive-QTOF	splash10-000f-9100000000-a26bbdbd0f7dd29afdf3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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

FDB014331

KNApSAcK ID

Not Available

Chemspider ID

26910

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28930

PDB ID

Not Available

ChEBI ID

89044

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

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 (-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane (HMDB0035625)

MOL for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

3D MOL for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

3D SDF for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

3D-SDF for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

PDB for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

3D PDB for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

SMILES for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

INCHI for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

Structure for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

3D Structure for HMDB0035625 ((-)-7,7-Dimethyl-2-methylenebicyclo[2.2.1]heptane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra