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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:36 UTC

Update Date

2023-02-21 17:25:05 UTC

HMDB ID

HMDB0036127

Secondary Accession Numbers

HMDB36127

Metabolite Identification

Common Name

(-)-Pinocamphone

Description

(-)-Pinocamphone 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 (-)-Pinocamphone.

Structure

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

COMPND    HMDB0036127
HETATM    1  C1  UNL     1       2.477  -1.231   0.078  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.109  -0.742   0.565  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.314   0.636   1.059  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.212   0.889   1.846  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.448   1.736   0.620  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.497   1.228  -0.437  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.373   0.458  -1.447  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.113  -0.766  -0.558  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.146  -0.062  -0.117  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.545  -0.344   1.285  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.338  -0.290  -1.053  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.530  -1.054  -1.003  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.630  -2.277   0.353  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.301  -0.648   0.584  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.808  -1.395   1.403  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.116   2.489   0.106  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.081   2.264   1.412  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.101   1.976  -0.955  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.437   0.712  -1.413  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.099   0.358  -2.437  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.002  -1.707  -1.085  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.450   0.220   1.558  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.848  -1.431   1.332  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.781  -0.209   2.043  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.071  -0.094  -2.099  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.072   0.522  -0.773  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.841  -1.239  -0.866  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
Pinocamphone	HMDB
trans-3-Pinanone	HMDB
Pinocamphone, (1S-(1alpha,2beta,5alpha))-isomer	MeSH
Pinocamphone, (1alpha,2beta,5alpha)-isomer	MeSH

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(1S,2R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

Traditional Name

(1S,2R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

CAS Registry Number

22339-21-5

SMILES

C[C@@H]1[C@@H]2C[C@H](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/t6-,7-,8+/m1/s1

InChI Key

MQPHVIPKLRXGDJ-PRJMDXOYSA-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

Organoleptic effect

Odor

Spicy

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036127)

Source

Endogenous

Endogenous (HMDB: HMDB0036127)

Plant

Plant (HMDB: HMDB0036127)

Animal

Animal (HMDB: HMDB0036127)

Exogenous

Food

Food (HMDB: HMDB0036127)

Herb and spice

Herb

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0036127)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036127)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036127)

Lipid metabolism pathway (HMDB: HMDB0036127)

Cellular process

Cell signaling (HMDB: HMDB0036127)

Biochemical process

Lipid transport (HMDB: HMDB0036127)

Role

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	0.48 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]+	136.087	31661259
DarkChem	[M-H]-	134.764	31661259
DeepCCS	[M+H]+	145.338	30932474
DeepCCS	[M-H]-	142.943	30932474
DeepCCS	[M-2H]-	176.22	30932474
DeepCCS	[M+Na]+	151.251	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 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.	4.39 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5531 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2022.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	509.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	277.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	542.2 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	672.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1059.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	383.4 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	1274.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	397.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	457.5 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	36.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Pinocamphone	C[C@@H]1[C@@H]2C[C@H](CC1=O)C2(C)C	1542.0	Standard polar	33892256
(-)-Pinocamphone	C[C@@H]1[C@@H]2C[C@H](CC1=O)C2(C)C	1158.9	Standard non polar	33892256
(-)-Pinocamphone	C[C@@H]1[C@@H]2C[C@H](CC1=O)C2(C)C	1160.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Pinocamphone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C[C@H]2C[C@@H]1C2(C)C	1344.6	Semi standard non polar	33892256
(-)-Pinocamphone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C[C@H]2C[C@@H]1C2(C)C	1324.7	Standard non polar	33892256
(-)-Pinocamphone,1TMS,isomer #2	C[C@H]1C(O[Si](C)(C)C)=C[C@H]2C[C@@H]1C2(C)C	1285.3	Semi standard non polar	33892256
(-)-Pinocamphone,1TMS,isomer #2	C[C@H]1C(O[Si](C)(C)C)=C[C@H]2C[C@@H]1C2(C)C	1305.2	Standard non polar	33892256
(-)-Pinocamphone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C[C@H]2C[C@@H]1C2(C)C	1582.9	Semi standard non polar	33892256
(-)-Pinocamphone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C[C@H]2C[C@@H]1C2(C)C	1534.9	Standard non polar	33892256
(-)-Pinocamphone,1TBDMS,isomer #2	C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H]2C[C@@H]1C2(C)C	1553.6	Semi standard non polar	33892256
(-)-Pinocamphone,1TBDMS,isomer #2	C[C@H]1C(O[Si](C)(C)C(C)(C)C)=C[C@H]2C[C@@H]1C2(C)C	1497.1	Standard non polar	33892256

Spectra

GC-MS Spectra

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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB014975

KNApSAcK ID

C00053852

Chemspider ID

4932523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6427105

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

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 (-)-Pinocamphone (HMDB0036127)

MOL for HMDB0036127 ((-)-Pinocamphone)

3D MOL for HMDB0036127 ((-)-Pinocamphone)

3D SDF for HMDB0036127 ((-)-Pinocamphone)

3D-SDF for HMDB0036127 ((-)-Pinocamphone)

PDB for HMDB0036127 ((-)-Pinocamphone)

3D PDB for HMDB0036127 ((-)-Pinocamphone)

SMILES for HMDB0036127 ((-)-Pinocamphone)

INCHI for HMDB0036127 ((-)-Pinocamphone)

Structure for HMDB0036127 ((-)-Pinocamphone)

3D Structure for HMDB0036127 ((-)-Pinocamphone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra