Pharmakon1600-01504027

Details

• Internal ID: f24c6271-8470-455c-85d7-20845af7b940
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: (9R)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): C1C2CNCC1C3=CC=CC(=O)N3C2
• SMILES (Isomeric): C1[C@@H]2CNCC1C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9?/m1/s1
• InChI Key: ANJTVLIZGCUXLD-VEDVMXKPSA-N
• Popularity: 475 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24 g/mol
• Exact Mass: 190.110613074 g/mol
• Topological Polar Surface Area (TPSA): 32.30 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• SpecPlus_000618
• Spectrum2_000470
• Spectrum3_001611
• Spectrum4_001834
• Spectrum5_000627
• BSPBio_003241
• KBioGR_002534
• KBioSS_001945
• DivK1c_006714
• SPECTRUM1504027
• SPBio_000580
• SCHEMBL8309064
• CHEBI:95183
• KBio1_001658
• KBio2_001945
• KBio2_004513
• KBio2_007081
• KBio3_002461
• HMS1922B03
• Pharmakon1600-01504027
• LSM-6464
• CCG-39978
• NSC758665
• NSC-758665
• SDCCGMLS-0066826.P001
• NCGC00178191-01
• VU0243453-3
• BRD-A55579717-001-02-4
• BRD-A55579717-001-03-2
• Q27166989

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.7987	79.87%
Blood Brain Barrier	+	0.9317	93.17%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6243	62.43%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.9661	96.61%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.5400	54.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9367	93.67%
P-glycoprotein inhibitior	-	0.9712	97.12%
P-glycoprotein substrate	-	0.6696	66.96%
CYP3A4 substrate	-	0.5573	55.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7588	75.88%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9577	95.77%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9330	93.30%
CYP inhibitory promiscuity	+	0.5946	59.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7267	72.67%
Eye corrosion	-	0.9786	97.86%
Eye irritation	-	0.6937	69.37%
Skin irritation	-	0.7458	74.58%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6030	60.30%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.6743	67.43%
skin sensitisation	-	0.8417	84.17%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5521	55.21%
Estrogen receptor binding	-	0.7667	76.67%
Androgen receptor binding	-	0.6712	67.12%
Thyroid receptor binding	-	0.5430	54.30%
Glucocorticoid receptor binding	-	0.7837	78.37%
Aromatase binding	-	0.6466	64.66%
PPAR gamma	-	0.5737	57.37%
Honey bee toxicity	-	0.9134	91.34%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.8241	82.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	11 nM	EC50	via Super-PRED
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	280 nM	Ki	via Super-PRED
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	0.23 nM	Ki	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	96.11%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.48%	98.95%
CHEMBL222	P23975	Norepinephrine transporter	94.40%	96.06%
CHEMBL228	P31645	Serotonin transporter	94.28%	95.51%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.08%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.41%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.22%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.99%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.81%	93.40%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.10%	82.69%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.90%	96.25%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	81.82%	97.98%
CHEMBL1937	Q92769	Histone deacetylase 2	80.38%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.09%	97.25%

Plants that contains it

• Ammodendron bifolium
• Ammodendron karelinii
• Anagyris foetida
• Anarthrophyllum elegans
• Baptisia alba var. macrophylla
• Baptisia australis
• Baptisia nuttalliana
• Bolusanthus speciosus
• Dermatophyllum secundiflorum
• Dicraeopetalum stipulare
• Euchresta formosana
• Genista acanthoclada
• Genista libanotica
• Genista lobelii
• Genista maderensis
• Genista majorica
• Genista pilosa
• Gonocytisus pterocladus
• Laburnum alpinum
• Laburnum anagyroidis
• Lamprolobium grandiflorum
• Leontice leontopetalum
• Lupinus odoratus
• Melolobium microphyllum
• Osyris alba
• Pericopsis angolensis
• Petteria ramentacea
• Plagiocarpus axillaris
• Platycelyphium voense
• Polhillia pallens
• Retama raetam
• Sakoanala villosa
• Sophora alopecuroides
• Sophora flavescens
• Sophora macrocarpa
• Sophora pachycarpa
• Sophora velutina
• Spartium junceum
• Thermopsis alterniflora
• Thermopsis chinensis
• Thermopsis lanceolata
• Thermopsis montana

Cross-Links

• PubChem: 6708720
• NPASS: NPC147985
• LOTUS: LTS0111966
• wikiData: Q27166989