MiMeDB: Showing metabocard for 3-Oxo-beta-ionone (MMDBc0033577)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:19 UTC

Update Date

2025-10-07 16:08:01 UTC

Metabolite ID

MMDBc0033577

Metabolite Identification

Common Name

3-Oxo-beta-ionone

Description

3-Oxo-beta-ionone is a ketone belonging to the chemical class of terpenoids, specifically a derivative of beta-ionone. Its chemical structure features a cyclohexene ring with a ketone functional group at the 3-position, contributing to its reactivity and interaction in various biochemical pathways. In metabolic studies, it has been observed that rabbits dosed orally with beta-ionone excreted 3-oxo-beta-ionone along with other metabolites such as 3-oxo-beta-ionol and dihydro-3-oxo-beta-ionol in their urine (PMID:5488915 ). These metabolites were isolated and characterized as 2,4-dinitrophenylhydrazone and p-nitrobenzoate derivatives, confirming their identities through comparison with synthetic standards (PMID:5488915 ). The presence of 3-oxo-beta-ionone in metabolic pathways suggests its role in the breakdown and transformation of beta-ionone, highlighting its potential involvement in the metabolism of carotenoids and other terpenoid compounds within biological systems.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223192D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
 11  3  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033577

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)C=CC1=C(C)C(=O)CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O2/c1-9(14)5-6-11-10(2)12(15)7-8-13(11,3)4/h5-6H,7-8H2,1-4H3

> <INCHI_KEY>
OBHGOXFSRVNKBS-UHFFFAOYSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.46258460833264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.608340309

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.49102797973248

> <JCHEM_PKA_STRONGEST_BASIC>
-4.66465750739373

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
62.5153

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
3-oxo-b-Ionone	Generator
3-oxo-Β-ionone	Generator

Molecular Formula

C₁₃H₁₈O₂

Average Mass

206.2808

Monoisotopic Mass

206.13067982

IUPAC Name

2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

Traditional Name

2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-en-1-one

CAS Registry Number

27185-77-9

SMILES

CC(=O)C=CC1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C13H18O2/c1-9(14)5-6-11-10(2)12(15)7-8-13(11,3)4/h5-6H,7-8H2,1-4H3

InChI Key

OBHGOXFSRVNKBS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Cyclic ketone
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.61	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.52 m³·mol⁻¹	ChemAxon
Polarizability	23.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-3900000000-e07e3214c50514fd81db	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0950000000-82de7bcbf5ca14d2b2f6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052s-4910000000-b21c4dd1243c6c09c767	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-9500000000-00b17b7c231e59c0d0a2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0290000000-d6b8b009d962e9f08f75	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1790000000-5ebe9812818cbf1efc41	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-3900000000-e353efc723f307e518f3	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	361.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	23.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	471.2
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	654.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	581.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	489.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2259.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	67.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	506.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	570.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	512.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	272.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	184.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	317.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	127.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	355.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1339.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1303.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-Oxo-beta-ionone_TMS_1	CC(=O)C=CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C	standard non polar	2025-10-24	1718.49
Gas Chromatography	3-Oxo-beta-ionone_TMS_2	C=C(C=CC1=C(C)C(=O)CCC1(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	1665.04
Gas Chromatography	3-Oxo-beta-ionone_TMS_3	C=C(C=CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C)O[Si](C)(C)C	standard non polar	2025-10-24	2314.9
Gas Chromatography	3-Oxo-beta-ionone_TMS_1	CC(=O)C=CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C	standard polar	2025-10-24	2057.31
Gas Chromatography	3-Oxo-beta-ionone_TMS_2	C=C(C=CC1=C(C)C(=O)CCC1(C)C)O[Si](C)(C)C	standard polar	2025-10-24	1744.19
Gas Chromatography	3-Oxo-beta-ionone_TMS_3	C=C(C=CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C)O[Si](C)(C)C	standard polar	2025-10-24	2566.63

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

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

33736

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Loscos N, Hernandez-Orte P, Cacho J, Ferreira V: Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions. J Agric Food Chem. 2007 Aug 8;55(16):6674-84. doi: 10.1021/jf0702343. Epub 2007 Jul 7. [PubMed:17616208 ]

Showing metabocard for 3-Oxo-beta-ionone (MMDBc0033577)

MOL for #<Metabolite:0x00007f9ad577d4f0>

3D MOL for #<Metabolite:0x00007f9ad577d4f0>

3D SDF for #<Metabolite:0x00007f9ad577d4f0>

3D-SDF for #<Metabolite:0x00007f9ad577d4f0>

PDB for #<Metabolite:0x00007f9ad577d4f0>

3D PDB for #<Metabolite:0x00007f9ad577d4f0>

SMILES for #<Metabolite:0x00007f9ad577d4f0>

INCHI for #<Metabolite:0x00007f9ad577d4f0>

Structure for #<Metabolite:0x00007f9ad577d4f0>

3D Structure for #<Metabolite:0x00007f9ad577d4f0>