Jump To Section:

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 23:36:50 UTC

Update Date

2023-02-21 17:26:30 UTC

HMDB ID

HMDB0038321

Secondary Accession Numbers

HMDB38321

Metabolite Identification

Common Name

Homoarecoline

Description

Homoarecoline 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. Homoarecoline has been detected, but not quantified in, nuts. This could make homoarecoline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Homoarecoline.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   10                                                            
CONECT    3    1   12                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    4   10                                                       
CONECT    7    8   10                                                       
CONECT    8    5    7    9                                                  
CONECT    9    8   11   12                                                  
CONECT   10    2    6    7                                                  
CONECT   11    9                                                            
CONECT   12    3    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0038321
HETATM    1  C1  UNL     1       4.207   0.441  -0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.455  -0.836  -0.033  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.083  -0.708   0.278  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.206   0.057  -0.460  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.703   0.650  -1.451  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.209   0.202  -0.156  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.797  -0.387   0.863  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.212  -0.278   1.216  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.958   0.638   0.305  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.436   0.604  -1.063  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.502  -0.719  -1.613  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.063   1.056  -1.024  1.00  0.00           C  
HETATM   13  H1  UNL     1       5.272   0.218   0.205  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.217   0.943  -1.021  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.879   1.158   0.778  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.958  -1.563   0.634  1.00  0.00           H  
HETATM   17  H5  UNL     1       3.504  -1.263  -1.074  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.164  -1.011   1.495  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.295   0.137   2.254  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.684  -1.281   1.263  1.00  0.00           H  
HETATM   21  H9  UNL     1      -4.034   0.365   0.319  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.907   1.703   0.636  1.00  0.00           H  
HETATM   23  H11 UNL     1      -3.049  -0.731  -2.594  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.006  -1.413  -0.917  1.00  0.00           H  
HETATM   25  H13 UNL     1      -1.469  -1.095  -1.821  1.00  0.00           H  
HETATM   26  H14 UNL     1      -1.039   2.105  -0.611  1.00  0.00           H  
HETATM   27  H15 UNL     1      -0.662   1.009  -2.047  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   12
CONECT    7    8   18
CONECT    8    9   19   20
CONECT    9   10   21   22
CONECT   10   11   12
CONECT   11   23   24   25
CONECT   12   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Arecaidine ethyl ester	HMDB
Arecaidine-ethyl ester	HMDB
Ethyl 1-methyl-1,2,5,6-tetrahydronicotinate	HMDB
Nicotinic acid, 1,2,5,6-tetrahydro-1-methyl-, ethyl ester	HMDB
Ethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid	Generator

Chemical Formula

C₉H₁₅NO₂

Average Molecular Weight

169.2209

Monoisotopic Molecular Weight

169.110278729

IUPAC Name

ethyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Traditional Name

ethyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylate

CAS Registry Number

28125-84-0

SMILES

CCOC(=O)C1=CCCN(C)C1

InChI Identifier

InChI=1S/C9H15NO2/c1-3-12-9(11)8-5-4-6-10(2)7-8/h5H,3-4,6-7H2,1-2H3

InChI Key

UNARQANIGOBIHM-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038321)
Cytoplasm (HMDB: HMDB0038321)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038321)

Source

Exogenous

Food

Food (HMDB: HMDB0038321)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0038321)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038321)

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	51750 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	297 g/L	ALOGPS
logP	0.86	ALOGPS
logP	1.01	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Basic)	8.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.61 m³·mol⁻¹	ChemAxon
Polarizability	19.19 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.337	31661259
DarkChem	[M-H]-	135.773	31661259
DeepCCS	[M+H]+	141.206	30932474
DeepCCS	[M-H]-	138.496	30932474
DeepCCS	[M-2H]-	174.77	30932474
DeepCCS	[M+Na]+	150.175	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	139.9	32859911
AllCCS	[M+Na-2H]-	141.3	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Homoarecoline	CCOC(=O)C1=CCCN(C)C1	1751.2	Standard polar	33892256
Homoarecoline	CCOC(=O)C1=CCCN(C)C1	1272.7	Standard non polar	33892256
Homoarecoline	CCOC(=O)C1=CCCN(C)C1	1247.4	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 - Homoarecoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fs-9700000000-0d289ac37c6d60f6d6a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homoarecoline 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 - Homoarecoline 10V, Negative-QTOF	splash10-014i-1900000000-8779ad94aff4cbe7da58	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 20V, Negative-QTOF	splash10-01ba-4900000000-fde3fffe199184794715	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 40V, Negative-QTOF	splash10-0005-9200000000-3eac4de69a210d185f5a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 10V, Negative-QTOF	splash10-014i-0900000000-f4607bafa946b5c6f2fe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 20V, Negative-QTOF	splash10-00xr-2900000000-d0f502e0b4b1f1318bfb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 40V, Negative-QTOF	splash10-000w-9100000000-c951492f23a9ac8e44ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 10V, Positive-QTOF	splash10-00di-0900000000-b4b58c9562f2eb72678b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 20V, Positive-QTOF	splash10-00di-6900000000-557bd8c16b5b9ab402a5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 40V, Positive-QTOF	splash10-0fxw-9000000000-cf53537164440bd9b5ce	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 10V, Positive-QTOF	splash10-00di-1900000000-b3ccfa9033cd7f62d358	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 20V, Positive-QTOF	splash10-00dj-6900000000-e87ced3bfb6901b9e581	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homoarecoline 40V, Positive-QTOF	splash10-0005-9200000000-2490824d69449d26069a	2021-09-25	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

FDB017654

KNApSAcK ID

C00044165

Chemspider ID

31488

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

34167

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1513651

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 Homoarecoline (HMDB0038321)

MOL for HMDB0038321 (Homoarecoline)

3D MOL for HMDB0038321 (Homoarecoline)

3D SDF for HMDB0038321 (Homoarecoline)

3D-SDF for HMDB0038321 (Homoarecoline)

PDB for HMDB0038321 (Homoarecoline)

3D PDB for HMDB0038321 (Homoarecoline)

SMILES for HMDB0038321 (Homoarecoline)

INCHI for HMDB0038321 (Homoarecoline)

Structure for HMDB0038321 (Homoarecoline)

3D Structure for HMDB0038321 (Homoarecoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra