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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:32:17 UTC

Update Date

2023-02-21 17:29:28 UTC

HMDB ID

HMDB0059838

Secondary Accession Numbers

HMDB59838

Metabolite Identification

Common Name

Camphor

Description

Camphor, also known as (+)-camphor or (+)-bornan-2-one, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Camphor is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, camphor is primarily located in the membrane (predicted from logP). Camphor is a waxy, flammable, white or transparent solid with a strong aroma. It is a terpenoid with the chemical formula C10H16O. It is found in many plants, such as in the wood of the camphor laurel (Cinnamomum camphora), a large evergreen tree found in Asia (particularly in Sumatra and Borneo islands, Indonesia) and also of the unrelated Kapur tree, a tall timber tree from the same region. It also occurs in some other related trees in the laurel family, notably Ocotea usambarensis and in the oil in rosemary leaves (Rosmarinus officinalis). The mint family contains 10 to 20% camphor, while camphorweed (Heterotheca) only contains some 5%. Camphor can also be synthetically produced from oil of turpentine. It is used for its scent, as an ingredient in cooking (mainly in India), as an embalming fluid, for medicinal purposes, and in religious ceremonies. A major source of camphor in Asia is camphor basil (the parent of African blue basil) (Wikipedia ).

Structure

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

COMPND    HMDB0059838
HETATM    1  C1  UNL     1       1.446   1.037   0.898  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.705   0.229  -0.117  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.151   0.514  -1.507  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.736  -1.272   0.209  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.309  -1.800  -0.707  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.286  -0.644  -0.966  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.819   0.369   0.037  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.318   1.727  -0.119  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.980  -0.229   1.396  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.875   0.064   2.160  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.143  -1.220   1.611  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.361   0.506   1.206  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.779   1.305   1.743  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.759   2.002   0.404  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.247   0.686  -1.489  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.978  -0.309  -2.227  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.701   1.457  -1.883  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.712  -1.704   0.151  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.922  -2.568  -0.149  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.048  -2.238  -1.638  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.062  -0.295  -1.992  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.324  -0.949  -0.860  1.00  0.00           H  
HETATM   23  H12 UNL     1      -1.367   2.224   0.894  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.786   2.363  -0.821  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.388   1.696  -0.461  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.906  -0.767   2.274  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.240  -2.186   1.950  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    7
CONECT    3   15   16   17
CONECT    4    5   11   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9
CONECT    8   23   24   25
CONECT    9   10   10   11
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Bornan-2-one	ChEBI
(+)-Camphor	ChEBI
(1R)-(+)-Camphor	ChEBI
(1R,4R)-Camphor	ChEBI
(R)-(+)-Camphor	ChEBI
Camphor(D)	ChEBI
D-Camphor	ChEBI
Camphora	HMDB
CAMPHOR	ChEBI
(1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one	PhytoBank
(1R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one	PhytoBank
(+)-(1R,4R)-Camphor	PhytoBank
(1R)-Camphor	PhytoBank
(1R,4R)-(+)-Camphor	PhytoBank
(R)-Camphor	PhytoBank
D-(+)-Camphor	PhytoBank
Alcanfor	PhytoBank
(+)-2-Bornanone	PhytoBank
(±)-Camphor	PhytoBank
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one	PhytoBank
1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone	PhytoBank
1,7,7-Trimethylnorcamphor	PhytoBank
2-Bornanone	PhytoBank
2-Camphanone	PhytoBank
Alphanon	PhytoBank
Borneo camphor	PhytoBank
dl-Camphor	PhytoBank

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Traditional Name

(+)-camphor

CAS Registry Number

464-49-3

SMILES

CC1(C)[C@@H]2CC[C@@]1(C)C(=O)C2

InChI Identifier

InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m1/s1

InChI Key

DSSYKIVIOFKYAU-XCBNKYQSSA-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
Bornane monoterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

camphor (CHEBI:15396 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059838)

Source

Exogenous

Exogenous (HMDB: HMDB0059838)

Food

Herb and spice

Spice

Cinnamon (FooDB: FOOD00572)

Herb

Rosemary (FooDB: FOOD00159)
Common sage (FooDB: FOOD00165)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	176.00 to 177.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	204.00 to 205.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1600 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	2.380	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Baker	142.797	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	2.85	ALOGPS
logP	2.55	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	-7.5	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	44.49 m³·mol⁻¹	ChemAxon
Polarizability	17.74 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]+	134.353	31661259
DarkChem	[M-H]-	131.733	31661259
DeepCCS	[M-2H]-	173.704	30932474
DeepCCS	[M+Na]+	148.148	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	136.9	32859911
AllCCS	[M+HCOO]-	138.4	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. Predicted by Afia on May 17, 2022.	4.52 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0094 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Camphor	[H][C@@]12CC[C@@](C)(C(=O)C1)C2(C)C	1617.5	Standard polar	33892256
Camphor	[H][C@@]12CC[C@@](C)(C(=O)C1)C2(C)C	1147.9	Standard non polar	33892256
Camphor	[H][C@@]12CC[C@@](C)(C(=O)C1)C2(C)C	1143.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Camphor,1TMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C)[C@]1(C)CC2	1258.0	Semi standard non polar	33892256
Camphor,1TMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C)[C@]1(C)CC2	1252.2	Standard non polar	33892256
Camphor,1TMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C)[C@]1(C)CC2	1348.8	Standard polar	33892256
Camphor,1TBDMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)CC2	1500.9	Semi standard non polar	33892256
Camphor,1TBDMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)CC2	1380.1	Standard non polar	33892256
Camphor,1TBDMS,isomer #1	CC1(C)[C@H]2C=C(O[Si](C)(C)C(C)(C)C)[C@]1(C)CC2	1503.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

DB01744

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00000819

Chemspider ID

139902

KEGG Compound ID

Not Available

BioCyc ID

CPD-862

BiGG ID

Not Available

Wikipedia Link

Camphor

METLIN ID

Not Available

PubChem Compound

159055

PDB ID

Not Available

ChEBI ID

15396

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1056901

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Camphor (HMDB0059838)

MOL for HMDB0059838 (Camphor)

3D MOL for HMDB0059838 (Camphor)

3D SDF for HMDB0059838 (Camphor)

3D-SDF for HMDB0059838 (Camphor)

PDB for HMDB0059838 (Camphor)

3D PDB for HMDB0059838 (Camphor)

SMILES for HMDB0059838 (Camphor)

INCHI for HMDB0059838 (Camphor)

Structure for HMDB0059838 (Camphor)

3D Structure for HMDB0059838 (Camphor)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized