MiMeDB: Showing metabocard for 3-Methyl-4-octanolide (MMDBc0033574)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:12 UTC

Update Date

2024-04-30 20:12:59 UTC

Metabolite ID

MMDBc0033574

Metabolite Identification

Common Name

3-Methyl-4-octanolide

Description

Quercuslactone a 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. Quercuslactone a is a burnt, celery, and coconut tasting compound. Quercuslactone a has been detected, but not quantified in, alcoholic beverages. This could make quercuslactone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Quercuslactone a.

Structure

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

COMPND    HMDB0035307
HETATM    1  C1  UNL     1       4.075  -0.203  -0.282  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.821  -0.849   0.265  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.636  -0.061  -0.224  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.325  -0.614   0.260  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.760   0.279  -0.310  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.553   1.591   0.160  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.719   2.201   0.532  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.911   3.317   1.076  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.827   1.279   0.172  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.122  -0.071   0.234  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.830  -1.126  -0.544  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.623   0.312   0.560  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.835   0.608  -1.025  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.750  -0.961  -0.691  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.755  -1.887  -0.177  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.874  -0.936   1.349  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.611  -0.080  -1.331  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.717   0.977   0.171  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.149  -1.657  -0.060  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.228  -0.576   1.365  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.721   0.271  -1.403  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.217   1.473  -0.858  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.629   1.260   0.933  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.997  -0.301   1.311  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.316  -1.436  -1.465  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.875  -0.783  -0.788  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.922  -2.026   0.107  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   10   21
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   22   23
CONECT   10   11   24
CONECT   11   25   26   27
END

Synonyms

Value	Source
(e)-Whiskylactone	HMDB
T-Whiskylactone	HMDB
trans-Whiskeylactone	HMDB
beta-Methyl-gamma-octalactone	MeSH, HMDB
3-Methyl-4-butyl-g-butyrolactone	Generator
3-Methyl-4-butyl-γ-butyrolactone	Generator

Molecular Formula

C₉H₁₆O₂

Average Mass

156.2221

Monoisotopic Mass

156.115029756

IUPAC Name

5-butyl-4-methyloxolan-2-one

Traditional Name

cis-3-methyl-4-octanolide

CAS Registry Number

39212-23-2

SMILES

CCCCC1OC(=O)CC1C

InChI Identifier

InChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3

InChI Key

WNVCMFHPRIBNCW-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

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 heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.85 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.34	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-7	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	3	ChemAxon
Refractivity	42.92 m³·mol⁻¹	ChemAxon
Polarizability	18.11 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-9000000000-52b91f8a190dc4d70837	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-9000000000-52b91f8a190dc4d70837	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-7bc62b21db7f07d62ea5	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-eb60924d7db73dd90686	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-066s-9400000000-a3cfdd4ac40cb7f70218	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-bf75c35ed005be1d8a74	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-764fd7c479fc1a34fab7	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-2900000000-0d927d1c064257fc8d86	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-42902cc652512e92509c	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-5900000000-ec46ff9f1bd0520d6263	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-a3d29faf9e9c8b8eeddd	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ef700877a2790c9bfd8d	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-376389ca50b091133eac	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-8900000000-1b158ebc705577d08545	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-d89cdf27c92c75ba6b1d	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

Metabolic Reactions

Not Available

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

Source Type	Source Sub-type	Species	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

HMDB0035307

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014730

KNApSAcK ID

Not Available

Chemspider ID

56625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62900

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 3-Methyl-4-octanolide (MMDBc0033574)

MOL for #<Metabolite:0x0000559d035e2e28>

3D MOL for #<Metabolite:0x0000559d035e2e28>

3D SDF for #<Metabolite:0x0000559d035e2e28>

3D-SDF for #<Metabolite:0x0000559d035e2e28>

PDB for #<Metabolite:0x0000559d035e2e28>

3D PDB for #<Metabolite:0x0000559d035e2e28>

SMILES for #<Metabolite:0x0000559d035e2e28>

INCHI for #<Metabolite:0x0000559d035e2e28>

Structure for #<Metabolite:0x0000559d035e2e28>

3D Structure for #<Metabolite:0x0000559d035e2e28>