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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:07 UTC

Update Date

2023-02-21 17:19:31 UTC

HMDB ID

HMDB0030324

Secondary Accession Numbers

HMDB30324

Metabolite Identification

Common Name

(R)-Pelletierine

Description

(R)-Pelletierine 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 (R)-Pelletierine has been detected, but not quantified in, fruits and pomegranates (Punica granatum). This could make (R)-pelletierine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Pelletierine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Pelletierine	HMDB
(R)-(-)-Pelletierine	HMDB
(R)-1-(2-Piperidyl)acetone	HMDB
2-Acetonylpiperidine	MeSH
(-)-Isomer OF isopelletierine	MeSH
(+-)-Isomer OF isopelletierine	MeSH
Isopelletierine	MeSH
Pelletierine	MeSH

Chemical Formula

C₈H₁₅NO

Average Molecular Weight

141.2108

Monoisotopic Molecular Weight

141.115364107

IUPAC Name

1-[(2R)-piperidin-2-yl]propan-2-one

Traditional Name

1-[(2R)-piperidin-2-yl]propan-2-one

CAS Registry Number

2858-66-4

SMILES

CC(=O)C[C@H]1CCCCN1

InChI Identifier

InChI=1S/C8H15NO/c1-7(10)6-8-4-2-3-5-9-8/h8-9H,2-6H2,1H3/t8-/m1/s1

InChI Key

JEIZLWNUBXHADF-MRVPVSSYSA-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
Secondary aliphatic amine
Secondary amine
Azacycle
Amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030324)
Cytoplasm (HMDB: HMDB0030324)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030324)

Source

Endogenous

Endogenous (HMDB: HMDB0030324)

Plant

Plant (HMDB: HMDB0030324)

Exogenous

Food

Food (HMDB: HMDB0030324)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0030324)

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	19 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.76	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	18.51	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.84 m³·mol⁻¹	ChemAxon
Polarizability	16.46 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]+	132.359	31661259
DarkChem	[M-H]-	126.252	31661259
DeepCCS	[M+H]+	130.792	30932474
DeepCCS	[M-H]-	127.27	30932474
DeepCCS	[M-2H]-	164.442	30932474
DeepCCS	[M+Na]+	139.964	30932474
AllCCS	[M+H]+	130.5	32859911
AllCCS	[M+H-H2O]+	125.9	32859911
AllCCS	[M+NH4]+	134.8	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	135.2	32859911
AllCCS	[M+HCOO]-	137.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.16 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8663 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	191.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	819.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	270.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	255.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	257.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	571.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	647.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	172.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	712.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	762.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	408.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	175.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Pelletierine	CC(=O)C[C@H]1CCCCN1	1712.6	Standard polar	33892256
(R)-Pelletierine	CC(=O)C[C@H]1CCCCN1	1133.7	Standard non polar	33892256
(R)-Pelletierine	CC(=O)C[C@H]1CCCCN1	1174.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Pelletierine,1TMS,isomer #1	CC(=C[C@H]1CCCCN1)O[Si](C)(C)C	1393.3	Semi standard non polar	33892256
(R)-Pelletierine,1TMS,isomer #1	CC(=C[C@H]1CCCCN1)O[Si](C)(C)C	1418.4	Standard non polar	33892256
(R)-Pelletierine,1TMS,isomer #2	C=C(C[C@H]1CCCCN1)O[Si](C)(C)C	1346.9	Semi standard non polar	33892256
(R)-Pelletierine,1TMS,isomer #2	C=C(C[C@H]1CCCCN1)O[Si](C)(C)C	1387.1	Standard non polar	33892256
(R)-Pelletierine,1TMS,isomer #3	CC(=O)C[C@H]1CCCCN1[Si](C)(C)C	1326.0	Semi standard non polar	33892256
(R)-Pelletierine,1TMS,isomer #3	CC(=O)C[C@H]1CCCCN1[Si](C)(C)C	1383.0	Standard non polar	33892256
(R)-Pelletierine,2TMS,isomer #1	CC(=C[C@H]1CCCCN1[Si](C)(C)C)O[Si](C)(C)C	1483.7	Semi standard non polar	33892256
(R)-Pelletierine,2TMS,isomer #1	CC(=C[C@H]1CCCCN1[Si](C)(C)C)O[Si](C)(C)C	1511.8	Standard non polar	33892256
(R)-Pelletierine,2TMS,isomer #2	C=C(C[C@H]1CCCCN1[Si](C)(C)C)O[Si](C)(C)C	1424.3	Semi standard non polar	33892256
(R)-Pelletierine,2TMS,isomer #2	C=C(C[C@H]1CCCCN1[Si](C)(C)C)O[Si](C)(C)C	1550.2	Standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #1	CC(=C[C@H]1CCCCN1)O[Si](C)(C)C(C)(C)C	1616.6	Semi standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #1	CC(=C[C@H]1CCCCN1)O[Si](C)(C)C(C)(C)C	1582.8	Standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #2	C=C(C[C@H]1CCCCN1)O[Si](C)(C)C(C)(C)C	1565.6	Semi standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #2	C=C(C[C@H]1CCCCN1)O[Si](C)(C)C(C)(C)C	1586.2	Standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #3	CC(=O)C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C	1543.2	Semi standard non polar	33892256
(R)-Pelletierine,1TBDMS,isomer #3	CC(=O)C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C	1622.0	Standard non polar	33892256
(R)-Pelletierine,2TBDMS,isomer #1	CC(=C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1924.3	Semi standard non polar	33892256
(R)-Pelletierine,2TBDMS,isomer #1	CC(=C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1930.5	Standard non polar	33892256
(R)-Pelletierine,2TBDMS,isomer #2	C=C(C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1888.7	Semi standard non polar	33892256
(R)-Pelletierine,2TBDMS,isomer #2	C=C(C[C@H]1CCCCN1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1956.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Pelletierine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-533393079e14bac0f84f	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Pelletierine 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 - (R)-Pelletierine 10V, Positive-QTOF	splash10-006x-0900000000-4f2bbef7539b3808fbd6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 20V, Positive-QTOF	splash10-00ec-9800000000-b1da8444d30a3b4f2fc7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 40V, Positive-QTOF	splash10-0kai-9000000000-67a770bc38bc4ee983b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 10V, Negative-QTOF	splash10-0006-0900000000-f21c69abea97be9caad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 20V, Negative-QTOF	splash10-0006-7900000000-45983cc6a86e841f6c7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 40V, Negative-QTOF	splash10-0ac3-9200000000-2197c65b3c4b1ba2ef8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 10V, Negative-QTOF	splash10-0006-3900000000-f7ce90a5e2edb7e8df68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 20V, Negative-QTOF	splash10-052f-9500000000-6909e7965d715411d0c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 40V, Negative-QTOF	splash10-052f-9000000000-ad369aefaba23792157d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 10V, Positive-QTOF	splash10-001l-9800000000-0f53e9ce6fa75c5e673d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 20V, Positive-QTOF	splash10-001i-9100000000-5f2f71a7468d19b7afb4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Pelletierine 40V, Positive-QTOF	splash10-053r-9000000000-3db79e3dd61ee09e3c34	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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+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

FDB002167

KNApSAcK ID

C00002062

Chemspider ID

2299257

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3034881

PDB ID

Not Available

ChEBI ID

Not Available

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 (R)-Pelletierine (HMDB0030324)

MOL for HMDB0030324 ((R)-Pelletierine)

3D MOL for HMDB0030324 ((R)-Pelletierine)

3D SDF for HMDB0030324 ((R)-Pelletierine)

3D-SDF for HMDB0030324 ((R)-Pelletierine)

PDB for HMDB0030324 ((R)-Pelletierine)

3D PDB for HMDB0030324 ((R)-Pelletierine)

SMILES for HMDB0030324 ((R)-Pelletierine)

INCHI for HMDB0030324 ((R)-Pelletierine)

Structure for HMDB0030324 ((R)-Pelletierine)

3D Structure for HMDB0030324 ((R)-Pelletierine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra