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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:59:26 UTC

Update Date

2022-03-07 02:55:04 UTC

HMDB ID

HMDB0036814

Secondary Accession Numbers

HMDB36814

Metabolite Identification

Common Name

Santalone

Description

Santalone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Santalone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.699  -0.169   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.112  -0.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.360  -0.736   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.720   0.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.700   2.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.112   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.906   1.417   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.700   0.283   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.720  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.339  -1.756   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.153  -2.096   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.493   1.190   0.000  0.00  0.00           O+0
CONECT    1    2    9   12                                                  
CONECT    2    1    3    6   10                                             
CONECT    3    2    4    8   11                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    3    4    7                                                  
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   28    0
END

COMPND    HMDB0036814
HETATM    1  C1  UNL     1       2.733  -0.564  -0.294  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.499   0.205  -0.532  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.473   0.961  -1.501  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.359   0.045   0.381  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.705   0.412   1.772  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.192  -1.347   0.217  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.487  -1.314  -1.288  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.322  -0.021  -1.291  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.037   0.037  -0.008  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.576  -1.200   0.778  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.811   0.830  -0.187  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.771   2.305  -0.244  1.00  0.00           C  
HETATM   13  H1  UNL     1       2.527  -1.424   0.380  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.036  -1.017  -1.272  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.507   0.117   0.088  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.248  -0.431   2.245  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.121   0.733   2.409  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.444   1.256   1.729  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.400  -2.155   0.547  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.072  -2.179  -1.599  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.468  -1.175  -1.813  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.691   0.371  -2.229  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.028   0.435   0.146  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.254  -2.021   0.480  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.614  -0.964   1.840  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.792   2.681  -0.470  1.00  0.00           H  
HETATM   27  H15 UNL     1      -0.516   2.702   0.759  1.00  0.00           H  
HETATM   28  H16 UNL     1      -0.115   2.721  -1.045  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3    4
CONECT    4    5    6   11
CONECT    5   16   17   18
CONECT    6    7   10   19
CONECT    7    8   20   21
CONECT    8    9   11   22
CONECT    9   10   11   23
CONECT   10   24   25
CONECT   11   12
CONECT   12   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10,11,12,13-Tetranor-a-santalan-8-one	HMDB

Chemical Formula

C₁₁H₁₆O

Average Molecular Weight

164.2441

Monoisotopic Molecular Weight

164.120115134

IUPAC Name

1-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}ethan-1-one

Traditional Name

1-{2,3-dimethyltricyclo[2.2.1.0²,⁶]heptan-3-yl}ethanone

CAS Registry Number

59300-51-5

SMILES

CC(=O)C1(C)C2CC3C(C2)C13C

InChI Identifier

InChI=1S/C11H16O/c1-6(12)10(2)7-4-8-9(5-7)11(8,10)3/h7-9H,4-5H2,1-3H3

InChI Key

OTAKYGLQNSNZRX-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

Bornane monoterpenoid
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

Cytoplasm (HMDB: HMDB0036814)
Cell membrane (HMDB: HMDB0036814)

Cellular substructure

Extracellular (HMDB: HMDB0036814)
Membrane (HMDB: HMDB0036814)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036814)

Source

Endogenous

Endogenous (HMDB: HMDB0036814)

Animal

Animal (HMDB: HMDB0036814)

Exogenous

Food

Food (HMDB: HMDB0036814)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036814)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036814)

Cellular process

Cell signaling (HMDB: HMDB0036814)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036814)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036814)

Nutrient

Nutrient (HMDB: HMDB0036814)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036814)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0036814)

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	0.12 g/L	ALOGPS
logP	2.79	ALOGPS
logP	1.96	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.23	ChemAxon
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	1	ChemAxon
Refractivity	47.16 m³·mol⁻¹	ChemAxon
Polarizability	18.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.786	31661259
DarkChem	[M-H]-	129.868	31661259
DeepCCS	[M-2H]-	175.087	30932474
DeepCCS	[M+Na]+	150.311	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	130.1	32859911
AllCCS	[M+NH4]+	138.1	32859911
AllCCS	[M+Na]+	139.2	32859911
AllCCS	[M-H]-	140.6	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Santalone	CC(=O)C1(C)C2CC3C(C2)C13C	1500.6	Standard polar	33892256
Santalone	CC(=O)C1(C)C2CC3C(C2)C13C	1158.0	Standard non polar	33892256
Santalone	CC(=O)C1(C)C2CC3C(C2)C13C	1196.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Santalone,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1(C)C2CC3C(C2)C31C	1274.2	Semi standard non polar	33892256
Santalone,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1(C)C2CC3C(C2)C31C	1352.5	Standard non polar	33892256
Santalone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CC3C(C2)C31C	1543.3	Semi standard non polar	33892256
Santalone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2CC3C(C2)C31C	1542.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Santalone GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-7900000000-d9d4292ef2d580ebfd5a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Santalone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Santalone 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 - Santalone 10V, Positive-QTOF	splash10-014i-0900000000-bbc5e834601ce3655e0e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 20V, Positive-QTOF	splash10-014i-0900000000-b14328e53f33586616d3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 40V, Positive-QTOF	splash10-000t-0900000000-09ed8d3bac3f3cfd3bff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 10V, Negative-QTOF	splash10-03di-0900000000-7d0a9ed3c8ebab7ac378	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 20V, Negative-QTOF	splash10-03di-0900000000-7f2cb43849df77695bc2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 40V, Negative-QTOF	splash10-006t-0900000000-7c606299e24c2a76757e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 10V, Positive-QTOF	splash10-014i-0900000000-2cbd1b6c8f6d778cf69a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 20V, Positive-QTOF	splash10-00xr-0900000000-b9335856a011d0da491d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 40V, Positive-QTOF	splash10-014i-2900000000-b734adc56e0a0b71a4c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 10V, Negative-QTOF	splash10-03di-0900000000-defd12a7f890bc945918	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 20V, Negative-QTOF	splash10-03di-0900000000-defd12a7f890bc945918	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santalone 40V, Negative-QTOF	splash10-03di-0900000000-520d5199784f9378e977	2021-09-24	Wishart 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

FDB015761

KNApSAcK ID

C00021855

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71438766

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 Santalone (HMDB0036814)

MOL for HMDB0036814 (Santalone)

3D MOL for HMDB0036814 (Santalone)

3D SDF for HMDB0036814 (Santalone)

3D-SDF for HMDB0036814 (Santalone)

PDB for HMDB0036814 (Santalone)

3D PDB for HMDB0036814 (Santalone)

SMILES for HMDB0036814 (Santalone)

INCHI for HMDB0036814 (Santalone)

Structure for HMDB0036814 (Santalone)

3D Structure for HMDB0036814 (Santalone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra