3-Hydroxy-11-norcytisine

Details

• Internal ID: 44e159cf-f988-4ef0-9226-bbf6837465d9
• Taxonomy: Organoheterocyclic compounds > Pyridodiazepines
• IUPAC Name: 5-hydroxy-7,11-diazatricyclo[7.2.1.02,7]dodeca-2,4-dien-6-one
• SMILES (Canonical): C1C2CNC1C3=CC=C(C(=O)N3C2)O
• SMILES (Isomeric): C1C2CNC1C3=CC=C(C(=O)N3C2)O
• InChI: InChI=1S/C10H12N2O2/c13-9-2-1-8-7-3-6(4-11-7)5-12(8)10(9)14/h1-2,6-7,11,13H,3-5H2
• InChI Key: AFTDVOKQJZAVLI-UHFFFAOYSA-N
• Popularity: 474 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.21 g/mol
• Exact Mass: 192.089877630 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.22
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 3-hydroxy-11-norcytisine
• BDBM50548706

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	+	0.5386	53.86%
Blood Brain Barrier	+	0.7546	75.46%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5963	59.63%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9643	96.43%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.5000	50.00%
OCT2 inhibitior	-	0.6814	68.14%
BSEP inhibitior	-	0.9811	98.11%
P-glycoprotein inhibitior	-	0.9921	99.21%
P-glycoprotein substrate	-	0.8442	84.42%
CYP3A4 substrate	-	0.5846	58.46%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.7644	76.44%
CYP3A4 inhibition	-	0.6681	66.81%
CYP2C9 inhibition	-	0.7374	73.74%
CYP2C19 inhibition	-	0.7617	76.17%
CYP2D6 inhibition	-	0.6750	67.50%
CYP1A2 inhibition	+	0.5244	52.44%
CYP2C8 inhibition	-	0.9228	92.28%
CYP inhibitory promiscuity	+	0.7334	73.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.6216	62.16%
Skin irritation	-	0.7623	76.23%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7757	77.57%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8711	87.11%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.4782	47.82%
Acute Oral Toxicity (c)	III	0.5128	51.28%
Estrogen receptor binding	-	0.7398	73.98%
Androgen receptor binding	-	0.5752	57.52%
Thyroid receptor binding	+	0.5746	57.46%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.8108	81.08%
PPAR gamma	-	0.6014	60.14%
Honey bee toxicity	-	0.9353	93.53%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.6849	68.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1978	P11511	Cytochrome P450 19A1	94.78%	91.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.57%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	92.66%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.60%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.13%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.02%	93.99%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.14%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.46%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.75%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	83.66%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.87%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.24%	94.45%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	80.61%	98.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.06%	92.94%

Plants that contains it

• Laburnum anagyroidis

Cross-Links

• PubChem: 74426088
• LOTUS: LTS0115782
• wikiData: Q104911556