Ricinine

Details

• Internal ID: 2453ae33-8971-49ac-899c-43ac1e3ec703
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > 3-pyridinecarbonitriles
• IUPAC Name: 4-methoxy-1-methyl-2-oxopyridine-3-carbonitrile
• SMILES (Canonical): CN1C=CC(=C(C1=O)C#N)OC
• SMILES (Isomeric): CN1C=CC(=C(C1=O)C#N)OC
• InChI: 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
• Popularity: 295 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16 g/mol
• Exact Mass: 164.058577502 g/mol
• Topological Polar Surface Area (TPSA): 53.30 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.27
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 524-40-3
• Ricinin
• Ricidine
• Ritsinin
• Recinine
• 1,2-Dihydro-4-methoxy-1-methyl-2-oxonicotinonitrile
• NSC 409913
• NSC 642604
• 4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 3-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-1-methyl-2-oxo-
• EINECS 208-359-7
• NSC409913
• NSC642604
• 4-methoxy-1-methyl-2-oxopyridine-3-carbonitrile
• BRN 0139222
• UNII-130UFS7AE0
• 130UFS7AE0
• CHEBI:18043
• Recinine-d3
• NSC-409913
• NSC-642604
• Nicotinonitrile, 1,2-dihydro-4-methoxy-1-methyl-2-oxo-
• 1,2-Dihydro-4-methoxy-1-methyl-2-oxo-3-pyridinecarbonitrile
• 5-22-07-00318 (Beilstein Handbook Reference)
• 1,2-dihydro-4-methoxy-1-methyl-2-oxo-3-pyridimecarbonitrile
• Prestwick_1041
• Ricinine-(methyl-d3)
• RICININE [MI]
• Prestwick0_000678
• Prestwick1_000678
• Prestwick2_000678
• Prestwick3_000678
• TimTec1_001989
• Oprea1_847597
• BSPBio_000775
• MLS001048969
• SCHEMBL257955
• SPBio_002696
• 4-methoxy-1-methyl-2-oxohydropyridine-3-carbonitrile
• BPBio1_000853
• MEGxp0_000747
• CHEMBL1329957
• ACon1_001266
• DTXSID50200412
• PETSAYFQSGAEQY-UHFFFAOYSA-N
• WLN: T6NVJ A1 CCN DO1
• HMS1539K09
• HMS1570G17
• HMS2097G17
• HMS2268G21
• TNP00192
• CCG-36061
• STL564798
• AKOS003673683
• Ricinine, >=95% (LC/MS-ELSD)
• NCGC00016487-01
• NCGC00016487-02
• NCGC00016487-03
• NCGC00016487-04
• NCGC00016487-05
• NCGC00142397-01
• NCGC00169517-01
• NCGC00169517-02
• CAS-524-40-3
• LS-96650
• SMR000386989
• HY-121944
• CS-0083725
• FT-0632288
• FT-0674423
• C01526
• E88580
• 4-methoxy-1-methyl-2-oxo-pyridine-3-carbonitrile
• Q907865
• 1,2-Dihydro-4-methoxy-1-methyl-2-oxo-Nicotinonitrile
• BRD-K82561139-001-01-9
• BRD-K82561139-001-05-0
• Nicotinonitrile,2-dihydro-4-methoxy-1-methyl-2-oxo-
• 3-Pyridinecarbonitrile,2-dihydro-4-methoxy-1-methyl-2-oxo-
• 1,2-Dihydro-1-methyl-4-methoxy-2-oxo-3-pyridine carbonitrile
• 4-Methoxy-1-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9678	96.78%
Caco-2	+	0.8945	89.45%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8498	84.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9565	95.65%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6926	69.26%
P-glycoprotein inhibitior	-	0.9601	96.01%
P-glycoprotein substrate	-	0.9519	95.19%
CYP3A4 substrate	-	0.5405	54.05%
CYP2C9 substrate	-	0.7765	77.65%
CYP2D6 substrate	-	0.8437	84.37%
CYP3A4 inhibition	-	0.8998	89.98%
CYP2C9 inhibition	-	0.9549	95.49%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9251	92.51%
CYP inhibitory promiscuity	-	0.8510	85.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8840	88.40%
Carcinogenicity (trinary)	Non-required	0.5879	58.79%
Eye corrosion	-	0.9772	97.72%
Eye irritation	+	0.6702	67.02%
Skin irritation	-	0.8216	82.16%
Skin corrosion	-	0.9732	97.32%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5803	58.03%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.8625	86.25%
skin sensitisation	-	0.9086	90.86%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6683	66.83%
Acute Oral Toxicity (c)	III	0.4946	49.46%
Estrogen receptor binding	-	0.9143	91.43%
Androgen receptor binding	-	0.5914	59.14%
Thyroid receptor binding	-	0.7597	75.97%
Glucocorticoid receptor binding	-	0.5939	59.39%
Aromatase binding	-	0.7062	70.62%
PPAR gamma	-	0.7749	77.49%
Honey bee toxicity	-	0.8905	89.05%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	-	0.8735	87.35%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3397	P11712	Cytochrome P450 2C9	12589.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	1778.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL1871	P10275	Androgen Receptor	95.48%	96.43%
CHEMBL2581	P07339	Cathepsin D	91.48%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.79%	86.33%
CHEMBL2535	P11166	Glucose transporter	88.21%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.70%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.98%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.88%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.43%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.63%	85.14%

Plants that contains it

• Bussea sakalava
• Ricinus communis
• Vicia lens

Cross-Links

• PubChem: 10666
• NPASS: NPC78625
• ChEMBL: CHEMBL1329957
• LOTUS: LTS0115465
• wikiData: Q907865