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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:44 UTC

Update Date

2023-02-21 17:29:06 UTC

HMDB ID

HMDB0042006

Secondary Accession Numbers

HMDB42006

Metabolite Identification

Common Name

Ricinine

Description

Ricinine, also known as ritsinin, belongs to the class of organic compounds known as 3-pyridinecarbonitriles. These are organic compounds containing a pyridine ring substituted at the 3-position by a carbonitrile group. Ricinine exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on Ricinine.

Structure

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

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.667  -1.540   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   12                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5    7    8                                                  
CONECT    7    3    6   12                                                  
CONECT    8    6   10   11                                                  
CONECT    9    5                                                            
CONECT   10    1    4    8                                                  
CONECT   11    8                                                            
CONECT   12    2    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridimecarbonitrile	ChEBI
1,2-Dihydro-4-methoxy-1-methyl-2-oxo-nicotinonitrile	HMDB
1,2-Dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile	HMDB
4-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile	HMDB
Ricidine	HMDB
Ricinin	HMDB
Ritsinin	HMDB
3-Cyano-4-methoxy-N-methyl-2-pyridone	HMDB

Chemical Formula

C₈H₈N₂O₂

Average Molecular Weight

164.1613

Monoisotopic Molecular Weight

164.05857751

IUPAC Name

4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Traditional Name

ricinine

CAS Registry Number

524-40-3

SMILES

COC1=C(C#N)C(=O)N(C)C=C1

InChI Identifier

InChI=1S/C8H8N2O2/c1-10-4-3-7(12-2)6(5-9)8(10)11/h3-4H,1-2H3

InChI Key

PETSAYFQSGAEQY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-pyridinecarbonitriles. These are organic compounds containing a pyridine ring substituted at the 3-position by a carbonitrile group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

3-pyridinecarbonitriles

Direct Parent

3-pyridinecarbonitriles

Alternative Parents

Substituents

3-pyridinecarbonitrile
Alkyl aryl ether
Dihydropyridine
Pyridinone
Hydropyridine
Vinylogous ester
Heteroaromatic compound
Lactam
Nitrile
Carbonitrile
Ether
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

nitrile (CHEBI:18043 )
pyridone (CHEBI:18043 )
pyridine alkaloid (CHEBI:18043 )
Pyridine alkaloids (C01526 )
a small molecule (RICININE )

Ontology

Not Available

Exogenous (HMDB: HMDB0042006)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	201.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.7 mg/mL at 10 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.97 g/L	ALOGPS
logP	0.15	ALOGPS
logP	-0.23	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.64 m³·mol⁻¹	ChemAxon
Polarizability	16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	135.491	31661259
DarkChem	[M-H]-	132.198	31661259
DeepCCS	[M+H]+	136.67	30932474
DeepCCS	[M-H]-	133.89	30932474
DeepCCS	[M-2H]-	169.921	30932474
DeepCCS	[M+Na]+	145.439	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.2	32859911
AllCCS	[M+NH4]+	137.8	32859911
AllCCS	[M+Na]+	139.0	32859911
AllCCS	[M-H]-	132.6	32859911
AllCCS	[M+Na-2H]-	133.7	32859911
AllCCS	[M+HCOO]-	135.0	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.	3.09 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7444 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1315.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	326.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	118.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	296.9 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	488.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	185.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	782.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	288.1 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	914.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	413.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.0 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	66.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ricinine	COC1=C(C#N)C(=O)N(C)C=C1	1904.5	Standard polar	33892256
Ricinine	COC1=C(C#N)C(=O)N(C)C=C1	1393.8	Standard non polar	33892256
Ricinine	COC1=C(C#N)C(=O)N(C)C=C1	2041.0	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 - Ricinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-4900000000-321ddd4c129b416f9989	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ricinine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ricinine LC-ESI-QTOF , positive-QTOF	splash10-014i-0900000000-adab020a4d76cab3928c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ricinine LC-ESI-QTOF , positive-QTOF	splash10-02ti-0900000000-02608c6cedb37af73052	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ricinine 20V, Positive-QTOF	splash10-02ti-0900000000-02608c6cedb37af73052	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ricinine 10V, Positive-QTOF	splash10-014i-0900000000-adab020a4d76cab3928c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 10V, Positive-QTOF	splash10-014i-0900000000-3ea696494e6f6bd7dd7b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 20V, Positive-QTOF	splash10-014i-0900000000-75dc3ae2f7fa7eb80c8c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 40V, Positive-QTOF	splash10-057r-9600000000-40364f307dd31abfce46	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 10V, Negative-QTOF	splash10-03di-1900000000-1095e06c59142c52f1cc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 20V, Negative-QTOF	splash10-03di-2900000000-7b202cf17a7df0c87048	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 40V, Negative-QTOF	splash10-0159-9100000000-7692bf6e6f487b66f940	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 10V, Negative-QTOF	splash10-03di-0900000000-666b2aeab867b0a7de8a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 20V, Negative-QTOF	splash10-03di-0900000000-03619af47fceb04e9d0d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 40V, Negative-QTOF	splash10-0pc0-2900000000-a08db21e440de4dbd99d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 10V, Positive-QTOF	splash10-014i-0900000000-91d0403ea721455992fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 20V, Positive-QTOF	splash10-014i-1900000000-5dc133ac53660a246d54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ricinine 40V, Positive-QTOF	splash10-0fr6-9300000000-fcf77c7edeab3dab019e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Not Available

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

Not Available

KNApSAcK ID

C00002069

Chemspider ID

10216

KEGG Compound ID

C01526

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ricinine

METLIN ID

Not Available

PubChem Compound

10666

PDB ID

Not Available

ChEBI ID

18043

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

Not Available

Showing metabocard for Ricinine (HMDB0042006)

MOL for HMDB0042006 (Ricinine)

3D MOL for HMDB0042006 (Ricinine)

3D SDF for HMDB0042006 (Ricinine)

3D-SDF for HMDB0042006 (Ricinine)

PDB for HMDB0042006 (Ricinine)

3D PDB for HMDB0042006 (Ricinine)

SMILES for HMDB0042006 (Ricinine)

INCHI for HMDB0042006 (Ricinine)

Structure for HMDB0042006 (Ricinine)

3D Structure for HMDB0042006 (Ricinine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra