Arecoline

Details

• Internal ID: f96d3502-9735-4fbe-9dd9-06a40144b159
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
• SMILES (Canonical): CN1CCC=C(C1)C(=O)OC
• SMILES (Isomeric): CN1CCC=C(C1)C(=O)OC
• InChI: InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
• InChI Key: HJJPJSXJAXAIPN-UHFFFAOYSA-N
• Popularity: 2,532 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19 g/mol
• Exact Mass: 155.094628657 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 63-75-2
• Arecolin
• Arecaline
• Arecholine
• Methylarecaiden
• Methylarecaidin
• Arekolin
• Arecoline base
• Arecaidine methyl ester
• 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
• methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
• Arecholin
• methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
• Methyl N-methyltetrahydronicotinate
• C8H13NO2
• N-Methyltetrahydronicotinic acid, methyl ester
• Methyl 1,2,5,6-tetrahydro-1-methylnicotinate
• NSC 56321
• Methyl N-methyl-1,2,5,6-tetrahydronicotinate
• CCRIS 7688
• 1,2,5,6-Tetrahydro-1-methylnicotinic acid, methyl ester
• EINECS 200-565-5
• NSC-56321
• BRN 0123045
• NICOTINIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-, METHYL ESTER
• UNII-4ALN5933BH
• 1-Methyl-delta(sup 3,4)tetrahydro-3-pyridinecarboxylate
• 4ALN5933BH
• CHEBI:2814
• 63-75-2 (free)
• DTXSID3022617
• 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester
• NCGC00015075-04
• N-Methyltetrahydropyridine-beta-carboxylic acid methyl ester
• 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
• DTXCID502617
• N-Methyl-.delta.-tetrahydronicotinic acid methyl ester
• methyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylate
• N-Methyltetrahydropyridine-.beta.-carboxylic acid methyl ester
• MLS000028840
• Arecaidine methyl ester;Arecoline base;Methyl arecaidin; Methylarecaidine; NSC56321
• CAS-63-75-2
• SMR000058258
• Arecoline_major
• Methylarecaidine
• ?arecoline
• arecolin-
• arecoline;hydrobromide
• Spectrum_000055
• ARECOLINE [MI]
• Prestwick0_000402
• Prestwick1_000402
• Prestwick2_000402
• Prestwick3_000402
• Spectrum2_000051
• Spectrum3_001387
• Spectrum4_000810
• Spectrum5_001316
• Lopac-A-6134
• D07EFM
• cid_9301
• CHEMBL7303
• Lopac0_000049
• SCHEMBL44065
• BSPBio_000324
• BSPBio_002974
• GTPL296
• KBioGR_001299
• KBioSS_000435
• DivK1c_000810
• SPBio_000201
• SPBio_002263
• BPBio1_000358
• MEGxp0_001891
• ACon1_002372
• BDBM46858
• KBio1_000810
• KBio2_000435
• KBio2_003003
• KBio2_005571
• KBio3_002194
• pyranosyl)-?-D-galactopyranoside
• NINDS_000810
• WLN: T6N CUTJ A1 CVO1
• NSC56321
• Tox21_110079
• BBL036229
• MFCD00059167
• AKOS000520752
• Tox21_110079_1
• CCG-204145
• DB04365
• SB54186
• SDCCGMLS-0066647.P001
• SDCCGSBI-0050038.P004
• IDI1_000810
• NCGC00015075-01
• NCGC00015075-02
• NCGC00015075-03
• NCGC00015075-05
• NCGC00015075-06
• NCGC00015075-07
• NCGC00015075-10
• NCGC00015075-19
• NCGC00162053-01
• NCGC00162053-02
• NCGC00162053-03
• AC-34025
• CAS-300-08-3
• LS-96624
• SBI-0050038.P003
• Methyl N-methyl-1,5,6-tetrahydronicotinate
• N-Methyl-beta -carboxylic acid methyl ester
• FT-0622470
• Methyl 1,5,6-tetrahydro-1-methylnicotinate
• EN300-40737
• A13071
• AB00053580_08
• AB00053580_09
• Methyl 1,2,5, 6-tetrahydro-1-methylnicotinate
• Methyl N-methyl-1,2,5, 6-tetrahydronicotinate
• A820142
• L000795
• Q423515
• n-methyltetrahydronicotinicacidmethylesterhydrobromide
• SR-01000075307-9
• BRD-K88646909-004-05-5
• BRD-K88646909-004-06-3
• BRD-K88646909-004-10-5
• 1,5,6-Tetrahydro-1-methylnicotinic acid, methyl ester
• Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate
• Nicotinic acid,2,5,6-tetrahydro-1-methyl-, methyl ester
• Methyl 1-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate #
• 3-Pyridinecarboxylic acid,2,5,6-tetrahydro-1-methyl-, methyl ester
• methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate;hydrobromide
• 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid, methyl ester
• 1-Methyl-1,2,5,6-tertrahydro-pyridine-3-carboxylicacid methyl ester
• 4-Nitrophenyl 2-Acetamido-2-deoxy-(6-O-2-acetamido-2-deoxy-?-D-gluco-
• 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylic acid methyl ester;hydrobromide
• InChI=1/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9244	92.44%
Caco-2	+	0.9559	95.59%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5352	53.52%
OATP2B1 inhibitior	-	0.8475	84.75%
OATP1B1 inhibitior	+	0.9619	96.19%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.9331	93.31%
P-glycoprotein inhibitior	-	0.9908	99.08%
P-glycoprotein substrate	-	0.8762	87.62%
CYP3A4 substrate	-	0.6190	61.90%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.7040	70.40%
CYP3A4 inhibition	-	0.9820	98.20%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9061	90.61%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9673	96.73%
CYP inhibitory promiscuity	-	0.9564	95.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.6491	64.91%
Eye corrosion	-	0.8227	82.27%
Eye irritation	+	0.7637	76.37%
Skin irritation	+	0.4915	49.15%
Skin corrosion	-	0.6782	67.82%
Ames mutagenesis	+	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5997	59.97%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6659	66.59%
skin sensitisation	-	0.7411	74.11%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4724	47.24%
Acute Oral Toxicity (c)	III	0.7876	78.76%
Estrogen receptor binding	-	0.9711	97.11%
Androgen receptor binding	-	0.7878	78.78%
Thyroid receptor binding	-	0.8920	89.20%
Glucocorticoid receptor binding	-	0.9127	91.27%
Aromatase binding	-	0.8288	82.88%
PPAR gamma	-	0.9407	94.07%
Honey bee toxicity	-	0.9706	97.06%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.7315	73.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	65000 nM; 115 nM; 115500 nM; 545 nM; 145000 nM	IC50; IC50; IC50; IC50; IC50	PMID: 9435896; PMID: 11597415; PMID: 11597415; PMID: 1433209; PMID: 9438027
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	1800 nM; 40 nM; 4500 nM	IC50; Ki; IC50	PMID: 9435896; via Super-PRED; PMID: 9438027
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	58000 nM; 11000 nM	IC50; IC50	PMID: 9438027; PMID: 9435896
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	26 nM; 13500 nM; 47500 nM	Ki; IC50; IC50	via Super-PRED; PMID: 9435896; PMID: 9438027
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	62500 nM	IC50	PMID: 9438027
CHEMBL1293235	P02545	Prelamin-A/C	1000 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	35.5 nM; 35.5 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.43%	96.09%
CHEMBL4208	P20618	Proteasome component C5	95.92%	90.00%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.21%	85.14%
CHEMBL4072	P07858	Cathepsin B	83.74%	93.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.87%	95.56%

Plants that contains it

• Areca catechu
• Piper betle

Cross-Links

• PubChem: 2230
• NPASS: NPC14437
• ChEMBL: CHEMBL7303
• LOTUS: LTS0116578
• wikiData: Q423515