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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 02:45:08 UTC

Update Date

2021-09-23 02:45:08 UTC

HMDB ID

HMDB0301817

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Sabinone

Description

(+)-sabinone 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. Thus, (+)-sabinone is considered to be an isoprenoid lipid molecule (+)-sabinone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-sabinone can be found in common sage, which makes (+)-sabinone a potential biomarker for the consumption of this food product.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      25.498 -19.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.837 -17.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.837 -19.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.165 -19.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.471 -21.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.498 -16.750   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.165 -17.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.118 -21.745   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.777 -21.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.498 -15.203   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.819 -16.730   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      27.841 -16.348   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    3   12                                             
CONECT    3    1    2                                                       
CONECT    4    1    7                                                       
CONECT    5    1    8    9                                                  
CONECT    6    2   10    7                                                  
CONECT    7    4   11    6                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1S,5S)-Sabinone	ChEBI

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

IUPAC Name

(1S,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

Traditional Name

(+)-sabinone

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]1(CC(=O)C2=C)C(C)C

InChI Identifier

InChI=1S/C10H14O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8H,3-5H2,1-2H3/t8-,10+/m1/s1

InChI Key

PBLWMCQDAGOTPV-SCZZXKLOSA-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
Thujane 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

enone (CHEBI:15403 )
p-menthane monoterpenoid (CHEBI:15403 )
Bicyclic monoterpenoids (C01868 )
Cyclic monoterpenes (C01868 )
Bicyclic monoterpenoids (LMPR0102120049 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301817)

Food

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.58	ALOGPS
logP	2.19	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-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	1	ChemAxon
Refractivity	44.34 m³·mol⁻¹	ChemAxon
Polarizability	17.4 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
AllCCS	[M+H]+	131.499	32859911
AllCCS	[M+H-H2O]+	127.179	32859911
AllCCS	[M+Na]+	136.687	32859911
AllCCS	[M+NH4]+	135.526	32859911
AllCCS	[M-H]-	135.689	32859911
AllCCS	[M+Na-2H]-	136.816	32859911
AllCCS	[M+HCOO]-	138.124	32859911
DeepCCS	[M-2H]-	169.487	30932474
DeepCCS	[M+Na]+	143.932	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Sabinone,1TMS,isomer #1	C=C1C(O[Si](C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1239.5	Semi standard non polar	33892256
(+)-Sabinone,1TMS,isomer #1	C=C1C(O[Si](C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1281.6	Standard non polar	33892256
(+)-Sabinone,1TMS,isomer #1	C=C1C(O[Si](C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1510.5	Standard polar	33892256
(+)-Sabinone,1TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1461.7	Semi standard non polar	33892256
(+)-Sabinone,1TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1467.3	Standard non polar	33892256
(+)-Sabinone,1TBDMS,isomer #1	C=C1C(O[Si](C)(C)C(C)(C)C)=C[C@]2(C(C)C)C[C@H]12	1670.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 10V, Positive-QTOF	splash10-0udi-0900000000-b944a7850a2f4fe1d4cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 20V, Positive-QTOF	splash10-0udi-2900000000-0888c057c2e8c85e876d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 40V, Positive-QTOF	splash10-0fai-9100000000-c816c99aa63863f47d6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 10V, Negative-QTOF	splash10-0002-0900000000-2421f2d51043c8d71dcc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 20V, Negative-QTOF	splash10-0002-0900000000-6a67a93e7026088246a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 40V, Negative-QTOF	splash10-00kf-8900000000-daaa6e6db8588b7f6606	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 10V, Positive-QTOF	splash10-0pbc-3900000000-8d90deaa01f6241e1218	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 20V, Positive-QTOF	splash10-0a4i-5900000000-555cbf2fda3d599bb222	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 40V, Positive-QTOF	splash10-0a6v-8900000000-253aef1b795834ba3d83	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 10V, Negative-QTOF	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 20V, Negative-QTOF	splash10-0002-0900000000-5ce140a6dd715a7bef21	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Sabinone 40V, Negative-QTOF	splash10-000t-2900000000-359e556b81359097e90b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001455

KNApSAcK ID

Not Available

Chemspider ID

388673

KEGG Compound ID

C01868

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

15403

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

Not Available

Showing metabocard for (+)-Sabinone (HMDB0301817)

MOL for HMDB0301817 ((+)-Sabinone)

3D MOL for HMDB0301817 ((+)-Sabinone)

3D SDF for HMDB0301817 ((+)-Sabinone)

3D-SDF for HMDB0301817 ((+)-Sabinone)

PDB for HMDB0301817 ((+)-Sabinone)

3D PDB for HMDB0301817 ((+)-Sabinone)

SMILES for HMDB0301817 ((+)-Sabinone)

INCHI for HMDB0301817 ((+)-Sabinone)

Structure for HMDB0301817 ((+)-Sabinone)

3D Structure for HMDB0301817 ((+)-Sabinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra