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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:37:57 UTC

Update Date

2023-02-21 17:28:31 UTC

HMDB ID

HMDB0041000

Secondary Accession Numbers

HMDB41000

Metabolite Identification

Common Name

Karahana lactone

Description

Karahana lactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Karahana lactone has been detected, but not quantified in, alcoholic beverages. This could make karahana lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Karahana lactone.

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  O   UNK     0      -0.370   2.802   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.792   1.322   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.158   0.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.899  -1.215   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.379  -1.639   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.265  -2.802   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.168  -2.167   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.379  -0.582   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.379   0.898   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.052  -1.744   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.004  -0.898   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.216  -2.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    2    8                                                       
CONECT   10   11                                                            
CONECT   11    3    8   10   12                                             
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

8,8-dimethyl-2-methylidene-6-oxabicyclo[3.2.1]octan-7-one

Traditional Name

8,8-dimethyl-2-methylidene-6-oxabicyclo[3.2.1]octan-7-one

CAS Registry Number

28449-87-8

SMILES

CC1(C)C2CCC(=C)C1C(=O)O2

InChI Identifier

InChI=1S/C10H14O2/c1-6-4-5-7-10(2,3)8(6)9(11)12-7/h7-8H,1,4-5H2,2-3H3

InChI Key

LASOZNWHPDFLML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Oxepane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041000)
Cytoplasm (HMDB: HMDB0041000)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041000)

Source

Exogenous

Food

Food (HMDB: HMDB0041000)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0041000)

Biological role

Nutrient (HMDB: HMDB0041000)

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	1692 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	2.84 g/L	ALOGPS
logP	2.48	ALOGPS
logP	1.85	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.22 m³·mol⁻¹	ChemAxon
Polarizability	17.86 Å³	ChemAxon
Number of Rings	2	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]+	137.397	31661259
DarkChem	[M-H]-	132.317	31661259
DeepCCS	[M+H]+	140.398	30932474
DeepCCS	[M-H]-	136.676	30932474
DeepCCS	[M-2H]-	174.069	30932474
DeepCCS	[M+Na]+	149.584	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.4	32859911
AllCCS	[M+Na]+	140.5	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	137.9	32859911
AllCCS	[M+HCOO]-	138.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Karahana lactone	CC1(C)C2CCC(=C)C1C(=O)O2	2004.1	Standard polar	33892256
Karahana lactone	CC1(C)C2CCC(=C)C1C(=O)O2	1351.3	Standard non polar	33892256
Karahana lactone	CC1(C)C2CCC(=C)C1C(=O)O2	1334.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Karahana lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbi-9600000000-e4631f92257527b24211	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Karahana lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Karahana lactone 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 - Karahana lactone 10V, Positive-QTOF	splash10-014i-0900000000-2d436383d8500d38e730	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 20V, Positive-QTOF	splash10-014i-0900000000-b98160ed491008b618bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 40V, Positive-QTOF	splash10-0a4r-9200000000-e52986cdf69e3c4fc5a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 10V, Negative-QTOF	splash10-014i-0900000000-9ff58ffd79c2e40536c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 20V, Negative-QTOF	splash10-01b9-0900000000-5e4c233b1d2afdaf9581	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 40V, Negative-QTOF	splash10-00di-1900000000-7f40861d9291aa211860	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 10V, Positive-QTOF	splash10-014i-0900000000-44c1b0c30e22805a36d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 20V, Positive-QTOF	splash10-00xr-0900000000-3c52e1c15053ccba7810	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 40V, Positive-QTOF	splash10-0a59-9400000000-3dd85fc2205bf2f0f70a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 20V, Negative-QTOF	splash10-01b9-0900000000-9cd811c4fa11dcf2d5ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Karahana lactone 40V, Negative-QTOF	splash10-00ds-0900000000-f945ae94b05b8abd4f6c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

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

FDB020860

KNApSAcK ID

Not Available

Chemspider ID

28570936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72978332

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1888601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Karahana lactone (HMDB0041000)

MOL for HMDB0041000 (Karahana lactone)

3D MOL for HMDB0041000 (Karahana lactone)

3D SDF for HMDB0041000 (Karahana lactone)

3D-SDF for HMDB0041000 (Karahana lactone)

PDB for HMDB0041000 (Karahana lactone)

3D PDB for HMDB0041000 (Karahana lactone)

SMILES for HMDB0041000 (Karahana lactone)

INCHI for HMDB0041000 (Karahana lactone)

Structure for HMDB0041000 (Karahana lactone)

3D Structure for HMDB0041000 (Karahana lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra