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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:08 UTC

Update Date

2023-02-21 17:19:31 UTC

HMDB ID

HMDB0030326

Secondary Accession Numbers

HMDB30326

Metabolite Identification

Common Name

Methylisopelletierine

Description

Methylisopelletierine belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms. Methylisopelletierine has been detected, but not quantified in, fruits and pomegranates (Punica granatum). This could make methylisopelletierine a potential biomarker for the consumption of these foods. Methylisopelletierine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Methylisopelletierine.

Structure

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

COMPND    HMDB0030326
HETATM    1  C1  UNL     1       3.793  -0.510   0.581  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.310  -0.413   0.581  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.705  -1.185   1.294  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.627   0.575  -0.247  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.141   0.571  -0.209  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.447   0.807   1.174  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.918   1.074   0.985  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.587   0.252  -0.050  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.827   0.043  -1.319  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.506  -0.479  -0.937  1.00  0.00           N  
HETATM   11  C9  UNL     1      -0.748  -1.690  -0.227  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.129  -0.851  -0.435  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.170  -1.204   1.350  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.209   0.508   0.704  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.910   0.466  -1.337  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.040   1.596   0.006  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.169   1.523  -0.770  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.039   1.738   1.555  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.220   0.012   1.883  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.014   2.152   0.694  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.491   0.969   1.932  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.541   0.787  -0.334  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.929  -0.745   0.307  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.674   0.975  -1.859  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.378  -0.730  -1.909  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.690  -2.157  -0.653  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.956  -1.596   0.841  1.00  0.00           H  
HETATM   28  H17 UNL     1       0.023  -2.486  -0.407  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5   15   16
CONECT    5    6   10   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11
CONECT   11   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
a-N-Methylpelletierin-b-one	HMDB
Methylpelletierine	HMDB

Chemical Formula

C₉H₁₇NO

Average Molecular Weight

155.2374

Monoisotopic Molecular Weight

155.131014171

IUPAC Name

1-(1-methylpiperidin-2-yl)propan-2-one

Traditional Name

N-methylpelletierine

CAS Registry Number

Not Available

SMILES

CN1CCCCC1CC(C)=O

InChI Identifier

InChI=1S/C9H17NO/c1-8(11)7-9-5-3-4-6-10(9)2/h9H,3-7H2,1-2H3

InChI Key

TYHJMEIBGDDCPA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Beta-aminoketone
Piperidine
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic nitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

citraconoyl group (CHEBI:7321 )
Piperidine alkaloids (C06184 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030326)
Cytoplasm (HMDB: HMDB0030326)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030326)

Source

Endogenous

Endogenous (HMDB: HMDB0030326)

Plant

Plant (HMDB: HMDB0030326)

Exogenous

Food

Food (HMDB: HMDB0030326)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030326)

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
Water Solubility	106 g/L	ALOGPS
logP	1.15	ALOGPS
logP	1.14	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	18.52	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.14 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.176	31661259
DarkChem	[M-H]-	132.417	31661259
DeepCCS	[M+H]+	138.059	30932474
DeepCCS	[M-H]-	135.922	30932474
DeepCCS	[M-2H]-	171.78	30932474
DeepCCS	[M+Na]+	146.742	30932474
AllCCS	[M+H]+	134.4	32859911
AllCCS	[M+H-H2O]+	129.9	32859911
AllCCS	[M+NH4]+	138.5	32859911
AllCCS	[M+Na]+	139.7	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	142.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylisopelletierine	CN1CCCCC1CC(C)=O	1729.2	Standard polar	33892256
Methylisopelletierine	CN1CCCCC1CC(C)=O	1161.0	Standard non polar	33892256
Methylisopelletierine	CN1CCCCC1CC(C)=O	1216.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylisopelletierine,1TMS,isomer #1	CC(=CC1CCCCN1C)O[Si](C)(C)C	1362.0	Semi standard non polar	33892256
Methylisopelletierine,1TMS,isomer #1	CC(=CC1CCCCN1C)O[Si](C)(C)C	1341.1	Standard non polar	33892256
Methylisopelletierine,1TMS,isomer #2	C=C(CC1CCCCN1C)O[Si](C)(C)C	1315.3	Semi standard non polar	33892256
Methylisopelletierine,1TMS,isomer #2	C=C(CC1CCCCN1C)O[Si](C)(C)C	1363.3	Standard non polar	33892256
Methylisopelletierine,1TBDMS,isomer #1	CC(=CC1CCCCN1C)O[Si](C)(C)C(C)(C)C	1583.5	Semi standard non polar	33892256
Methylisopelletierine,1TBDMS,isomer #1	CC(=CC1CCCCN1C)O[Si](C)(C)C(C)(C)C	1522.4	Standard non polar	33892256
Methylisopelletierine,1TBDMS,isomer #2	C=C(CC1CCCCN1C)O[Si](C)(C)C(C)(C)C	1569.6	Semi standard non polar	33892256
Methylisopelletierine,1TBDMS,isomer #2	C=C(CC1CCCCN1C)O[Si](C)(C)C(C)(C)C	1554.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylisopelletierine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9300000000-cfdf367203c3b75bb8f2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylisopelletierine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylisopelletierine 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 - Methylisopelletierine 10V, Positive-QTOF	splash10-0a4r-0900000000-3cdd066b30a1a70da370	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 20V, Positive-QTOF	splash10-000b-9700000000-ed683671392a5da3c10a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 40V, Positive-QTOF	splash10-0kfx-9100000000-25dcc54343f3efd90fa9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 10V, Negative-QTOF	splash10-0udi-0900000000-183203bf2901d5b62d3c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 20V, Negative-QTOF	splash10-0udi-2900000000-71e48bb0167f5d1fa375	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 40V, Negative-QTOF	splash10-052u-9300000000-ec440a69dc90fa723556	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 10V, Positive-QTOF	splash10-08fs-3900000000-0f6eb6aad41e032b77a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 20V, Positive-QTOF	splash10-01p2-7900000000-6e228c73fc34c2bfa562	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 40V, Positive-QTOF	splash10-0005-9000000000-d73698ec4672e6bca523	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 10V, Negative-QTOF	splash10-0zfr-6900000000-3ffd064781aeae2c3c50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 20V, Negative-QTOF	splash10-0zfu-9800000000-b4f17f9e289c35850fcd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylisopelletierine 40V, Negative-QTOF	splash10-052f-9200000000-d7233e30205278dd1f19	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86786

PDB ID

Not Available

ChEBI ID

7321

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

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

Showing metabocard for Methylisopelletierine (HMDB0030326)

MOL for HMDB0030326 (Methylisopelletierine)

3D MOL for HMDB0030326 (Methylisopelletierine)

3D SDF for HMDB0030326 (Methylisopelletierine)

3D-SDF for HMDB0030326 (Methylisopelletierine)

PDB for HMDB0030326 (Methylisopelletierine)

3D PDB for HMDB0030326 (Methylisopelletierine)

SMILES for HMDB0030326 (Methylisopelletierine)

INCHI for HMDB0030326 (Methylisopelletierine)

Structure for HMDB0030326 (Methylisopelletierine)

3D Structure for HMDB0030326 (Methylisopelletierine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra