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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:39:56 UTC

Update Date

2022-03-07 02:54:35 UTC

HMDB ID

HMDB0035656

Secondary Accession Numbers

HMDB35656

Metabolite Identification

Common Name

3-Pinanone

Description

3-Pinanone 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 3-Pinanone.

Structure

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

COMPND    HMDB0035656
HETATM    1  C1  UNL     1       2.075  -1.283   1.041  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.522  -0.286   0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.354   1.064   0.615  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.003   1.481   1.548  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.333   1.960   0.007  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.652   1.124  -0.770  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.056   0.237  -1.790  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.267  -0.731  -0.612  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.990  -0.173  -0.038  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.150  -0.086   1.418  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.200  -0.803  -0.716  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.720  -2.319   0.817  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.862  -1.026   2.078  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.198  -1.350   0.960  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.306  -0.196  -0.760  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.882   2.639  -0.682  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.243   2.510   0.774  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.556   1.618  -1.120  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.657  -0.147  -2.546  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.991   0.673  -2.169  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.211  -1.789  -0.920  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.775  -0.966   1.982  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.740   0.834   1.895  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.256  -0.052   1.651  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.880  -1.282   0.024  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.906  -1.599  -1.429  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.775  -0.053  -1.310  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    8   15
CONECT    3    4    4    5
CONECT    5    6   16   17
CONECT    6    7    9   18
CONECT    7    8   19   20
CONECT    8    9   21
CONECT    9   10   11
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6,6-trimethylbicyclo[3.1.1]Heptan-3-one, 9ci	HMDB
Pinocamphone, (1alpha,2beta,5alpha)-isomer	MeSH, HMDB
Pinocamphone, (1S-(1alpha,2beta,5alpha))-isomer	MeSH, HMDB
Pinocamphone	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

Traditional Name

2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

CAS Registry Number

15358-88-0

SMILES

CC1C2CC(CC1=O)C2(C)C

InChI Identifier

InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3

InChI Key

MQPHVIPKLRXGDJ-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

Pinane monoterpenoid
Bicyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035656)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035656)

Source

Endogenous

Endogenous (HMDB: HMDB0035656)

Animal

Animal (HMDB: HMDB0035656)

Exogenous

Food

Food (HMDB: HMDB0035656)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035656)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035656)

Cellular process

Cell signaling (HMDB: HMDB0035656)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035656)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035656)

Nutrient

Nutrient (HMDB: HMDB0035656)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035656)

Emulsifier (HMDB: HMDB0035656)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	212.00 to 213.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	199.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.343 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	2.25	ALOGPS
logP	2.28	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	17.95 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]+	135.127	31661259
DarkChem	[M-H]-	129.705	31661259
DeepCCS	[M+H]+	138.974	30932474
DeepCCS	[M-H]-	136.138	30932474
DeepCCS	[M-2H]-	172.471	30932474
DeepCCS	[M+Na]+	148.008	30932474
AllCCS	[M+H]+	132.1	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	139.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Pinanone	CC1C2CC(CC1=O)C2(C)C	1584.0	Standard polar	33892256
3-Pinanone	CC1C2CC(CC1=O)C2(C)C	1135.7	Standard non polar	33892256
3-Pinanone	CC1C2CC(CC1=O)C2(C)C	1162.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Pinanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC2CC1C2(C)C	1343.4	Semi standard non polar	33892256
3-Pinanone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CC2CC1C2(C)C	1293.1	Standard non polar	33892256
3-Pinanone,1TMS,isomer #2	CC1C(O[Si](C)(C)C)=CC2CC1C2(C)C	1285.9	Semi standard non polar	33892256
3-Pinanone,1TMS,isomer #2	CC1C(O[Si](C)(C)C)=CC2CC1C2(C)C	1263.3	Standard non polar	33892256
3-Pinanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC2CC1C2(C)C	1582.7	Semi standard non polar	33892256
3-Pinanone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CC2CC1C2(C)C	1522.2	Standard non polar	33892256
3-Pinanone,1TBDMS,isomer #2	CC1C(O[Si](C)(C)C(C)(C)C)=CC2CC1C2(C)C	1552.1	Semi standard non polar	33892256
3-Pinanone,1TBDMS,isomer #2	CC1C(O[Si](C)(C)C(C)(C)C)=CC2CC1C2(C)C	1466.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Pinanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-1900000000-108b84154b6482743dbc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Pinanone 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 - 3-Pinanone 10V, Positive-QTOF	splash10-0udi-0900000000-390ef432ea9d03ab16ac	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 20V, Positive-QTOF	splash10-0udi-0900000000-c0e8496aef565d9ab637	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 40V, Positive-QTOF	splash10-000i-0900000000-1903c593ccff3b95f0ec	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 10V, Negative-QTOF	splash10-0udi-0900000000-6066fb1fa4e911fcb744	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 20V, Negative-QTOF	splash10-0udi-0900000000-8bac9502125617ef6902	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 40V, Negative-QTOF	splash10-0f79-0900000000-858e87a1d9c8d7d1d208	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 20V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 40V, Negative-QTOF	splash10-0udj-0900000000-7772eb453c2cf9a7fd63	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 10V, Positive-QTOF	splash10-0f79-0900000000-1956de293f3cf23842aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 20V, Positive-QTOF	splash10-000i-0900000000-c83186b54c8f49a3bfff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Pinanone 40V, Positive-QTOF	splash10-0uy0-0900000000-670a8c4522c2375503a5	2021-09-24	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

FDB014371

KNApSAcK ID

C00037338

Chemspider ID

10570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11038

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1104631

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 3-Pinanone (HMDB0035656)

MOL for HMDB0035656 (3-Pinanone)

3D MOL for HMDB0035656 (3-Pinanone)

3D SDF for HMDB0035656 (3-Pinanone)

3D-SDF for HMDB0035656 (3-Pinanone)

PDB for HMDB0035656 (3-Pinanone)

3D PDB for HMDB0035656 (3-Pinanone)

SMILES for HMDB0035656 (3-Pinanone)

INCHI for HMDB0035656 (3-Pinanone)

Structure for HMDB0035656 (3-Pinanone)

3D Structure for HMDB0035656 (3-Pinanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra