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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:54:27 UTC

Update Date

2023-02-21 17:24:30 UTC

HMDB ID

HMDB0034973

Secondary Accession Numbers

HMDB34973

Metabolite Identification

Common Name

(R)-Campholenic aldehyde

Description

(R)-Campholenic aldehyde belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a significant number of articles have been published on (R)-Campholenic aldehyde.

Structure

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

COMPND    HMDB0034973
HETATM    1  C1  UNL     1      -2.654  -0.765   0.414  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.291  -0.574  -0.212  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.680  -1.386  -1.052  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.655  -0.895  -1.475  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.955   0.200  -0.478  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.778  -0.277   0.678  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.091  -0.819   0.271  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.844  -1.235   1.124  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.399   0.592   0.026  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.387   1.001   1.479  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.849   1.804  -0.776  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.410  -0.129  -0.046  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.494  -0.543   1.508  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.983  -1.805   0.365  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.178  -2.326  -1.366  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.568  -0.522  -2.509  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.374  -1.732  -1.362  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.499   1.006  -0.993  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.255  -1.060   1.268  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.968   0.592   1.335  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.414  -0.862  -0.756  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.194   1.928   1.572  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.449   1.278   1.731  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.094   0.202   2.158  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.035   2.468  -0.872  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.621   2.355  -0.232  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.142   1.502  -1.799  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    9
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6    9   18
CONECT    6    7   19   20
CONECT    7    8    8   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
2,2,3-Trimethyl-3-cyclopentene-1-acetaldehyde	ChEBI
2,2,3-Trimethylcyclopent-3-en-1-yl acetaldehyde	ChEBI
2-(2,2,3-Trimethylcyclopent-3-en-1-yl)acetaldehyde	ChEBI
alpha-Campholenic aldehyde	ChEBI
Campholenic aldehyde	ChEBI
a-Campholenic aldehyde	Generator
Α-campholenic aldehyde	Generator
(S)-2,2,3-Trimethylcyclopent-3-ene-1-acetaldehyde	HMDB
2,2,3-Trimethyl-3-cyclopenten-1-ylacetaldehyde	HMDB
FEMA 3592	HMDB
a-Campholenaldehyde	Generator
Α-campholenaldehyde	Generator

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-(2,2,3-trimethylcyclopent-3-en-1-yl)acetaldehyde

Traditional Name

campholenic aldehyde

CAS Registry Number

Not Available

SMILES

CC1=CCC(CC=O)C1(C)C

InChI Identifier

InChI=1S/C10H16O/c1-8-4-5-9(6-7-11)10(8,2)3/h4,7,9H,5-6H2,1-3H3

InChI Key

OGCGGWYLHSJRFY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Alpha-hydrogen aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alpha-CH2-containing aldehyde (CHEBI:48697 )
monocyclic compound (CHEBI:48697 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0034973)
Membrane (HMDB: HMDB0034973)

Sunflower (FooDB: FOOD00086)

Fruit

Fruits (FooDB: FOOD00871)

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Process

Not Available

Role

Not Available

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	111.2 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	1.16 g/L	ALOGPS
logP	3.17	ALOGPS
logP	1.94	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.07	ChemAxon
pKa (Strongest Basic)	-7	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	2	ChemAxon
Refractivity	47.32 m³·mol⁻¹	ChemAxon
Polarizability	18.06 Å³	ChemAxon
Number of Rings	1	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]+	134.581	31661259
DarkChem	[M-H]-	130.538	31661259
DeepCCS	[M+H]+	138.356	30932474
DeepCCS	[M-H]-	134.981	30932474
DeepCCS	[M-2H]-	172.099	30932474
DeepCCS	[M+Na]+	147.637	30932474
AllCCS	[M+H]+	132.7	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	136.9	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	140.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Campholenic aldehyde	CC1=CCC(CC=O)C1(C)C	1472.4	Standard polar	33892256
(R)-Campholenic aldehyde	CC1=CCC(CC=O)C1(C)C	1095.5	Standard non polar	33892256
(R)-Campholenic aldehyde	CC1=CCC(CC=O)C1(C)C	1152.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Campholenic aldehyde,1TMS,isomer #1	CC1=CCC(C=CO[Si](C)(C)C)C1(C)C	1323.6	Semi standard non polar	33892256
(R)-Campholenic aldehyde,1TMS,isomer #1	CC1=CCC(C=CO[Si](C)(C)C)C1(C)C	1203.7	Standard non polar	33892256
(R)-Campholenic aldehyde,1TBDMS,isomer #1	CC1=CCC(C=CO[Si](C)(C)C(C)(C)C)C1(C)C	1550.5	Semi standard non polar	33892256
(R)-Campholenic aldehyde,1TBDMS,isomer #1	CC1=CCC(C=CO[Si](C)(C)C(C)(C)C)C1(C)C	1446.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (R)-Campholenic aldehyde EI-B (Non-derivatized)	splash10-0a4m-9400000000-ce66a68f177fa4f618cc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-Campholenic aldehyde EI-B (Non-derivatized)	splash10-0a4m-9400000000-ce66a68f177fa4f618cc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Campholenic aldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-7900000000-0dccd0afc30157a9750d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Campholenic aldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Campholenic aldehyde 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 - (R)-Campholenic aldehyde 10V, Positive-QTOF	splash10-0udi-1900000000-95cee8f748d344cba3f0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 20V, Positive-QTOF	splash10-0udr-6900000000-d671c1ba36ee0ef4d694	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 40V, Positive-QTOF	splash10-1000-9000000000-cb4faa4cb7adc4caf1dd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-e31e37ef3b267377c510	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 20V, Negative-QTOF	splash10-0udi-1900000000-2e2bda27cdba16ab94aa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 40V, Negative-QTOF	splash10-0006-9400000000-9989252dc6b50c3eacad	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-47f7b14327bce0db8d41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 20V, Negative-QTOF	splash10-0zfr-0900000000-0ee3b7e3555d9ac139b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 40V, Negative-QTOF	splash10-014l-6900000000-998911867688f2fb25f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 10V, Positive-QTOF	splash10-0a4i-8900000000-498a56ea24176c519a36	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 20V, Positive-QTOF	splash10-0a4l-9300000000-db770cfc91913282c22e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Campholenic aldehyde 40V, Positive-QTOF	splash10-00nf-9000000000-4d24643cbaa73347eb30	2021-09-22	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

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

FDB013571

KNApSAcK ID

C00010805

Chemspider ID

88952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98497

PDB ID

Not Available

ChEBI ID

48697

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1530131

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 (R)-Campholenic aldehyde (HMDB0034973)

MOL for HMDB0034973 ((R)-Campholenic aldehyde)

3D MOL for HMDB0034973 ((R)-Campholenic aldehyde)

3D SDF for HMDB0034973 ((R)-Campholenic aldehyde)

3D-SDF for HMDB0034973 ((R)-Campholenic aldehyde)

PDB for HMDB0034973 ((R)-Campholenic aldehyde)

3D PDB for HMDB0034973 ((R)-Campholenic aldehyde)

SMILES for HMDB0034973 ((R)-Campholenic aldehyde)

INCHI for HMDB0034973 ((R)-Campholenic aldehyde)

Structure for HMDB0034973 ((R)-Campholenic aldehyde)

3D Structure for HMDB0034973 ((R)-Campholenic aldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra