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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:09:33 UTC

Update Date

2022-03-07 02:54:46 UTC

HMDB ID

HMDB0036091

Secondary Accession Numbers

HMDB36091

Metabolite Identification

Common Name

exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol

Description

exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Based on a literature review very few articles have been published on exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-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
5,6-dimethylbicyclo[2.2.1]Hept-5-en-2-ol, 9ci	HMDB
exo-Form	HMDB

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

5,6-dimethylbicyclo[2.2.1]hept-5-en-2-ol

Traditional Name

5,6-dimethylbicyclo[2.2.1]hept-5-en-2-ol

CAS Registry Number

Not Available

SMILES

CC1=C(C)C2CC1CC2O

InChI Identifier

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

InChI Key

BRMSNMZILBBMIX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0036091)

Exogenous

Food

Food (HMDB: HMDB0036091)

Exogenous (HMDB: HMDB0036091)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036091)

Role

Biological role

Energy source (HMDB: HMDB0036091)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036091)

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	11.6 g/L	ALOGPS
logP	1.32	ALOGPS
logP	1.15	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	18.61	ChemAxon
pKa (Strongest Basic)	-1.2	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	41.57 m³·mol⁻¹	ChemAxon
Polarizability	16.28 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]+	130.263	31661259
DarkChem	[M-H]-	125.294	31661259
DeepCCS	[M+H]+	131.528	30932474
DeepCCS	[M-H]-	128.061	30932474
DeepCCS	[M-2H]-	165.217	30932474
DeepCCS	[M+Na]+	140.408	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	125.9	32859911
AllCCS	[M+NH4]+	134.6	32859911
AllCCS	[M+Na]+	135.9	32859911
AllCCS	[M-H]-	132.3	32859911
AllCCS	[M+Na-2H]-	133.8	32859911
AllCCS	[M+HCOO]-	135.4	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.	3.42 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3492 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1638.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	342.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	131.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	339.1 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	496.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	751.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	332.4 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	979.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	238.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	375.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	349.1 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	146.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol	CC1=C(C)C2CC1CC2O	1694.5	Standard polar	33892256
exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol	CC1=C(C)C2CC1CC2O	1063.6	Standard non polar	33892256
exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol	CC1=C(C)C2CC1CC2O	1073.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol,1TMS,isomer #1	CC1=C(C)C2CC1CC2O[Si](C)(C)C	1229.1	Semi standard non polar	33892256
exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol,1TBDMS,isomer #1	CC1=C(C)C2CC1CC2O[Si](C)(C)C(C)(C)C	1458.3	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-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-102cf7dc85218c75bf5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol GC-MS (1 TMS) - 70eV, Positive	splash10-0abd-9700000000-13a032fb028f1ec26fa2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-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-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 10V, Positive-QTOF	splash10-00dr-0900000000-5e76a09c6ebd91be1ad6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 20V, Positive-QTOF	splash10-00dr-2900000000-2bb20dfc86a1df9dea3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 40V, Positive-QTOF	splash10-0pvi-9200000000-fcd929fd4c030a8267fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 10V, Negative-QTOF	splash10-000i-0900000000-4dfaa8dbaac33c480914	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 20V, Negative-QTOF	splash10-000i-0900000000-14868014567e206426ac	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 40V, Negative-QTOF	splash10-059l-5900000000-2a4c7f0b0b7977c92fc1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 10V, Positive-QTOF	splash10-0072-8900000000-cb20637da1d37d7aa5e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 20V, Positive-QTOF	splash10-052p-9200000000-918fc4a17dbbba9fcc35	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 40V, Positive-QTOF	splash10-0006-9000000000-7df60e99b93462c9478a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 20V, Negative-QTOF	splash10-000i-0900000000-5e24cce5d939b6f97b1b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol 40V, Negative-QTOF	splash10-014u-6900000000-98dfd21f28f5e41e301a	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

FDB014931

KNApSAcK ID

Not Available

Chemspider ID

35014091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101407815

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

Schmitz G, Braun V: Cell-bound and secreted proteases of Serratia marcescens. J Bacteriol. 1985 Mar;161(3):1002-9. [PubMed:2579058 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol (HMDB0036091)

MOL for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

3D MOL for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

3D SDF for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

3D-SDF for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

PDB for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

3D PDB for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

SMILES for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

INCHI for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

Structure for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

3D Structure for HMDB0036091 (exo-5,6-Dimethylbicyclo[2.2.1]hept-5-en-2-ol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra