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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:18 UTC

Update Date

2023-02-21 17:19:33 UTC

HMDB ID

HMDB0030352

Secondary Accession Numbers

HMDB30352

Metabolite Identification

Common Name

Arecaidine

Description

Arecaidine, also known as methylguvacine or isoguvacine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Based on a literature review a significant number of articles have been published on Arecaidine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid	HMDB
1,2,5,6-Tetrahydro-1-methyl-nicotinic acid	HMDB
1,2,5,6-Tetrahydro-1-methylnicotinic acid	HMDB
Arecaine	HMDB
Isoguvacine	HMDB
Methylguvacine	HMDB
N-Methylguvacine	HMDB

Chemical Formula

C₇H₁₁NO₂

Average Molecular Weight

141.1677

Monoisotopic Molecular Weight

141.078978601

IUPAC Name

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Traditional Name

arecaidine

CAS Registry Number

499-04-7

SMILES

CN1CCC=C(C1)C(O)=O

InChI Identifier

InChI=1S/C7H11NO2/c1-8-4-2-3-6(5-8)7(9)10/h3H,2,4-5H2,1H3,(H,9,10)

InChI Key

DNJFTXKSFAMXQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Hydropyridine
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

citraconoyl group (CHEBI:2813 )
Pyridine alkaloids (C10128 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030352)
Cytoplasm (HMDB: HMDB0030352)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030352)

Source

Endogenous

Endogenous (HMDB: HMDB0030352)

Plant

Plant (HMDB: HMDB0030352)

Exogenous

Food

Food (HMDB: HMDB0030352)

Nut

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	223 - 224 °C	Not Available
Boiling Point	266.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.770 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	510 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.5	ChemAxon
logS	0.56	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.09 m³·mol⁻¹	ChemAxon
Polarizability	14.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.8	31661259
DarkChem	[M-H]-	126.843	31661259
DeepCCS	[M+H]+	125.855	30932474
DeepCCS	[M-H]-	122.799	30932474
DeepCCS	[M-2H]-	159.584	30932474
DeepCCS	[M+Na]+	134.5	30932474
AllCCS	[M+H]+	128.8	32859911
AllCCS	[M+H-H2O]+	124.1	32859911
AllCCS	[M+NH4]+	133.1	32859911
AllCCS	[M+Na]+	134.3	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arecaidine	CN1CCC=C(C1)C(O)=O	2256.9	Standard polar	33892256
Arecaidine	CN1CCC=C(C1)C(O)=O	1232.5	Standard non polar	33892256
Arecaidine	CN1CCC=C(C1)C(O)=O	1289.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arecaidine,1TMS,isomer #1	CN1CCC=C(C(=O)O[Si](C)(C)C)C1	1306.3	Semi standard non polar	33892256
Arecaidine,1TBDMS,isomer #1	CN1CCC=C(C(=O)O[Si](C)(C)C(C)(C)C)C1	1540.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arecaidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-5016141f0956bcb61704	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arecaidine GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9610000000-ba3d6ec40b68f8644659	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arecaidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arecaidine 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 - Arecaidine 10V, Positive-QTOF	splash10-006x-2900000000-cbf6b06a5114ef9a45b7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 20V, Positive-QTOF	splash10-00di-7900000000-94f6afae9735d1e68f8e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 40V, Positive-QTOF	splash10-014l-9000000000-6306d85a79a8199479c9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 10V, Negative-QTOF	splash10-0006-3900000000-95905d59360919845f60	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 20V, Negative-QTOF	splash10-0002-9400000000-69008b534089006a1f92	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 40V, Negative-QTOF	splash10-001m-9000000000-874a616349f5d03fb027	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 10V, Negative-QTOF	splash10-0006-0900000000-5a83a2962aa54e2e941b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 20V, Negative-QTOF	splash10-0007-9500000000-3ad9a59a32e7884796ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 40V, Negative-QTOF	splash10-0006-9000000000-9bf56bbc51259b1bc9d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 10V, Positive-QTOF	splash10-0006-3900000000-4799c802d2ba0c9aebbe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 20V, Positive-QTOF	splash10-00xv-9300000000-afa7d9bffd770bac4610	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arecaidine 40V, Positive-QTOF	splash10-00kf-9000000000-67a3d38f6d5d4df8b6cb	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+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

Arecaidine

METLIN ID

Not Available

PubChem Compound

10355

PDB ID

Not Available

ChEBI ID

226311

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1389521

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 Arecaidine (HMDB0030352)

MOL for HMDB0030352 (Arecaidine)

3D MOL for HMDB0030352 (Arecaidine)

3D SDF for HMDB0030352 (Arecaidine)

3D-SDF for HMDB0030352 (Arecaidine)

PDB for HMDB0030352 (Arecaidine)

3D PDB for HMDB0030352 (Arecaidine)

SMILES for HMDB0030352 (Arecaidine)

INCHI for HMDB0030352 (Arecaidine)

Structure for HMDB0030352 (Arecaidine)

3D Structure for HMDB0030352 (Arecaidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra