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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:10:54 UTC

Update Date

2023-02-21 17:24:42 UTC

HMDB ID

HMDB0035229

Secondary Accession Numbers

HMDB35229

Metabolite Identification

Common Name

5-Isopropylbicyclo[3.1.0]hexan-2-one

Description

5-Isopropylbicyclo[3.1.0]hexan-2-one belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 5-Isopropylbicyclo[3.1.0]hexan-2-one has been detected, but not quantified in, herbs and spices and root vegetables. This could make 5-isopropylbicyclo[3.1.0]hexan-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Isopropylbicyclo[3.1.0]hexan-2-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(1-Methylethyl)-bicyclo(3.1.0)hexan-2-one	HMDB
5-(1-Methylethyl)-bicyclo[3.1.0]hexan-2-one	HMDB
5-(1-Methylethyl)bicyclo[3.1.0]hexan-2-one, 9ci	HMDB
5-Isopropyl-bicyclo[3.1.0]hexan-2-one	HMDB
5-isopropylbicyclo(3.1.0)Hexan-2-one	HMDB
Sabina ketone	HMDB
Sabinaketone	HMDB
Sabine ketone	HMDB

Chemical Formula

C₉H₁₄O

Average Molecular Weight

138.2069

Monoisotopic Molecular Weight

138.10446507

IUPAC Name

5-(propan-2-yl)bicyclo[3.1.0]hexan-2-one

Traditional Name

sabinaketone

CAS Registry Number

513-20-2

SMILES

CC(C)C12CC1C(=O)CC2

InChI Identifier

InChI=1S/C9H14O/c1-6(2)9-4-3-8(10)7(9)5-9/h6-7H,3-5H2,1-2H3

InChI Key

MDDYCNAAAZKNAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035229)
Cytoplasm (HMDB: HMDB0035229)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035229)

Source

Exogenous

Food

Food (HMDB: HMDB0035229)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0035229)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035229)

Biological role

Nutrient (HMDB: HMDB0035229)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	218.00 to 219.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1064 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.509 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.11 g/L	ALOGPS
logP	1.53	ALOGPS
logP	2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	19.9	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	39.99 m³·mol⁻¹	ChemAxon
Polarizability	16.06 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]+	130.666	31661259
DarkChem	[M-H]-	125.218	31661259
DeepCCS	[M-2H]-	167.492	30932474
DeepCCS	[M+Na]+	142.799	30932474
AllCCS	[M+H]+	129.5	32859911
AllCCS	[M+H-H2O]+	125.1	32859911
AllCCS	[M+NH4]+	133.7	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	132.9	32859911
AllCCS	[M+Na-2H]-	134.4	32859911
AllCCS	[M+HCOO]-	136.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Isopropylbicyclo[3.1.0]hexan-2-one	CC(C)C12CC1C(=O)CC2	1554.1	Standard polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one	CC(C)C12CC1C(=O)CC2	1095.1	Standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one	CC(C)C12CC1C(=O)CC2	1109.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TMS,isomer #1	CC(C)C12CCC(O[Si](C)(C)C)=C1C2	1187.9	Semi standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TMS,isomer #1	CC(C)C12CCC(O[Si](C)(C)C)=C1C2	1251.0	Standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TMS,isomer #2	CC(C)C12CC=C(O[Si](C)(C)C)C1C2	1207.0	Semi standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TMS,isomer #2	CC(C)C12CC=C(O[Si](C)(C)C)C1C2	1260.6	Standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TBDMS,isomer #1	CC(C)C12CCC(O[Si](C)(C)C(C)(C)C)=C1C2	1420.8	Semi standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TBDMS,isomer #1	CC(C)C12CCC(O[Si](C)(C)C(C)(C)C)=C1C2	1445.2	Standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TBDMS,isomer #2	CC(C)C12CC=C(O[Si](C)(C)C(C)(C)C)C1C2	1439.7	Semi standard non polar	33892256
5-Isopropylbicyclo[3.1.0]hexan-2-one,1TBDMS,isomer #2	CC(C)C12CC=C(O[Si](C)(C)C(C)(C)C)C1C2	1421.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0037-9200000000-0355a1852b4d9bf8409e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 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 - 5-Isopropylbicyclo[3.1.0]hexan-2-one 10V, Positive-QTOF	splash10-000i-1900000000-5d6be4be47787964e920	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 20V, Positive-QTOF	splash10-000i-5900000000-7cc03030626ebb2df99f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 40V, Positive-QTOF	splash10-0059-9100000000-180fe742a34e6ab8a31c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 10V, Negative-QTOF	splash10-000i-0900000000-631134e454e2483a605a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 20V, Negative-QTOF	splash10-000i-0900000000-9d4baeafff3166e385f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 40V, Negative-QTOF	splash10-0a4l-9600000000-4cf558959187fc38801f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 10V, Positive-QTOF	splash10-002e-9200000000-c19c602e06213ae5fade	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 20V, Positive-QTOF	splash10-0059-9200000000-3eced68a4001714598e4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 40V, Positive-QTOF	splash10-004r-9300000000-b69565b9c03954384a8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 10V, Negative-QTOF	splash10-000i-0900000000-928b413704490084a303	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 20V, Negative-QTOF	splash10-000i-0900000000-e2872db60585e58bbefe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Isopropylbicyclo[3.1.0]hexan-2-one 40V, Negative-QTOF	splash10-0170-5900000000-6d428d38282e9266cb03	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB013884

KNApSAcK ID

C00053762

Chemspider ID

83758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92784

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1382671

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 5-Isopropylbicyclo[3.1.0]hexan-2-one (HMDB0035229)

MOL for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

3D MOL for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

3D SDF for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

3D-SDF for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

PDB for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

3D PDB for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

SMILES for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

INCHI for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

Structure for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

3D Structure for HMDB0035229 (5-Isopropylbicyclo[3.1.0]hexan-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra