Anabasine

Details

• Internal ID: b48841e5-5bab-45a4-9dd9-ff8bf04b0334
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: 3-[(2S)-piperidin-2-yl]pyridine
• SMILES (Canonical): C1CCNC(C1)C2=CN=CC=C2
• SMILES (Isomeric): C1CCN[C@@H](C1)C2=CN=CC=C2
• InChI: InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2/t10-/m0/s1
• InChI Key: MTXSIJUGVMTTMU-JTQLQIEISA-N
• Popularity: 375 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₂
• Molecular Weight: 162.23 g/mol
• Exact Mass: 162.115698455 g/mol
• Topological Polar Surface Area (TPSA): 24.90 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.90
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Anabasine
• (-)-Anabasine
• Neonicotine
• (S)-anabasine
• (S)-3-(Piperidin-2-yl)pyridine
• Anabasin
• Neonikotin
• Anabazin
• S-(-)-Anabasine
• 3-[(2S)-piperidin-2-yl]pyridine
• L-3-(2'-Piperidyl)pyridine
• (-)-2-(3'-Pyridyl)piperidine
• Pyridine, 3-(2-piperidinyl)-, (S)-
• (S)-(-)-Anabasine
• Pyridine, 3-(2S)-2-piperidinyl-
• Piperidine, 2-(3-pyridyl)-
• Pyridine, 3-(2-piperidyl)-
• 2-(3-Pyridyl)piperidine
• 3-(2-Piperidinyl)pyridine
• L-(-)-Anabasine
• 2-(3'-Pyridyl) piperidine
• Caswell No. 051
• UNII-LMS11II2LO
• LMS11II2LO
• CHEBI:74
• NSC 87504
• HSDB 3462
• EINECS 207-791-3
• NSC-87504
• Pyridine, 3-(2-pyridyl) piperidine
• EPA Pesticide Chemical Code 006001
• BRN 0082637
• (S)-3-(2-Piperidinyl)pyridine
• 3-(2S)-2-Piperidinylpyridine
• DTXSID9041607
• 5-23-06-00096 (Beilstein Handbook Reference)
• CAS-494-52-0
• (2S)-2-(PYRIDIN-3-YL)PIPERIDINE
• 3-((2S)-piperidin-2-yl)pyridine
• NICOTINE IMPURITY G (EP IMPURITY)
• NICOTINE IMPURITY G [EP IMPURITY]
• NICOTINE RESINATE IMPURITY G (EP IMPURITY)
• NICOTINE RESINATE IMPURITY G [EP IMPURITY]
• MLS000737148
• 2-(3-Pyridinyl)piperidine #
• NICOTINE DITARTRATE DIHYDRATE IMPURITY G (EP IMPURITY)
• NICOTINE DITARTRATE DIHYDRATE IMPURITY G [EP IMPURITY]
• (S)-Snabasine
• L(-)-Anabasine
• -(-)-Anabasine
• MFCD00871391
• Tocris-1971
• ANABASINE [MI]
• ANABASINE [HSDB]
• ANABASINE [WHO-DD]
• Pesticide Code: 006001
• SCHEMBL3465120
• (S)-Anabasine, > 70% ee
• WLN: T6NJ C- BT6MTJ
• CHEMBL1526229
• DTXCID7021607
• US8609708, 59 Anabasine
• BDBM109767
• 3-(2-PIPERIDYL)-PYRIDINE
• (S)-3-(piperidin-2-yl)=pyridine
• HY-B1532
• NSC87504
• 2-(3'-PYRIDYL)-PIPERIDINE
• Pyridine,3-(2S)-2-piperidinyl-,
• Tox21_301952
• 1-3-(2'-PIPERIDYL)PYRIDINE
• AKOS000277110
• DISCONTINUED. Please see A637170
• NCGC00016468-01
• NCGC00025333-01
• NCGC00255520-01
• AC-35720
• AS-55183
• TS-01458
• CS-0013343
• (S)-Anabasine 100 microg/mL in Acetonitrile
• 3-[(2S)-Piperidin-2-yl]pyridine (Anabasine)
• EN300-691230
• Y10910
• (2S)-1,2,3,4,5,6-hexahydro-2,3'-bipyridinyl
• BRD-K94837957-003-01-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9910	99.10%
Caco-2	+	0.8758	87.58%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7005	70.05%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.9648	96.48%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	-	0.9418	94.18%
P-glycoprotein inhibitior	-	0.9897	98.97%
P-glycoprotein substrate	-	0.9297	92.97%
CYP3A4 substrate	-	0.7016	70.16%
CYP2C9 substrate	-	0.7388	73.88%
CYP2D6 substrate	+	0.5522	55.22%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8751	87.51%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6235	62.35%
CYP inhibitory promiscuity	-	0.7871	78.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7954	79.54%
Eye corrosion	-	0.6618	66.18%
Eye irritation	+	0.6983	69.83%
Skin irritation	+	0.5246	52.46%
Skin corrosion	+	0.5676	56.76%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8748	87.48%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.6632	66.32%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7655	76.55%
Acute Oral Toxicity (c)	III	0.4993	49.93%
Estrogen receptor binding	-	0.8450	84.50%
Androgen receptor binding	-	0.8452	84.52%
Thyroid receptor binding	-	0.7511	75.11%
Glucocorticoid receptor binding	-	0.8775	87.75%
Aromatase binding	-	0.7752	77.52%
PPAR gamma	-	0.7132	71.32%
Honey bee toxicity	-	0.9688	96.88%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.6851	68.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	5011.87 nM	AC50	via CMAUP
CHEMBL5282	P11509	Cytochrome P450 2A6	32400 nM	IC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	1995.26 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	7943.28 nM	AC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	95.73%	94.55%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.02%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	90.08%	92.88%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.17%	85.30%
CHEMBL2039	P27338	Monoamine oxidase B	88.72%	92.51%
CHEMBL1075145	P55072	Transitional endoplasmic reticulum ATPase	86.38%	98.50%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	86.26%	80.96%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.16%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.25%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.09%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	82.45%	91.49%
CHEMBL2996	Q05655	Protein kinase C delta	81.88%	97.79%
CHEMBL226	P30542	Adenosine A1 receptor	80.45%	95.93%

Plants that contains it

• Anabasis aphylla
• Cyphanthera tasmanica
• Duboisia myoporoides
• Gymnospermium darwasicum
• Haloxylon persicum
• Haloxylon salicornicum
• Liparia vestita
• Lupinus formosus
• Nicotiana africana
• Nicotiana glauca
• Nicotiana plumbaginifolia
• Nicotiana tabacum
• Saurauia excelsa
• Verbascum songaricum

Cross-Links

• PubChem: 205586
• NPASS: NPC146373
• ChEMBL: CHEMBL1526229
• LOTUS: LTS0200706
• wikiData: Q419308