Cytisine, N-formyl-

Details

• Internal ID: 4a9032cf-8c6b-40d8-90ab-ae63f16dee7f
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: 6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-diene-11-carbaldehyde
• InChI: InChI=1S/C12H14N2O2/c15-8-13-5-9-4-10(7-13)11-2-1-3-12(16)14(11)6-9/h1-3,8-10H,4-7H2
• InChI Key: PCYQRXYBKKZUSR-UHFFFAOYSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25 g/mol
• Exact Mass: 218.105527694 g/mol
• Topological Polar Surface Area (TPSA): 40.60 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 6-oxo-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-diene-11-carbaldehyde
• CHEMBL1433686
• DCA00706
• NCGC00017402-02
• NCGC00142626-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9872	98.72%
Caco-2	+	0.8529	85.29%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8077	80.77%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.9504	95.04%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	0.5023	50.23%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9021	90.21%
P-glycoprotein inhibitior	-	0.9791	97.91%
P-glycoprotein substrate	-	0.7845	78.45%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6048	60.48%
CYP2D6 substrate	-	0.8351	83.51%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9644	96.44%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8458	84.58%
CYP inhibitory promiscuity	+	0.6679	66.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6684	66.84%
Eye corrosion	-	0.9807	98.07%
Eye irritation	-	0.8412	84.12%
Skin irritation	-	0.7899	78.99%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5096	50.96%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.6724	67.24%
skin sensitisation	-	0.8621	86.21%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.7539	75.39%
Acute Oral Toxicity (c)	III	0.6026	60.26%
Estrogen receptor binding	-	0.6843	68.43%
Androgen receptor binding	-	0.5226	52.26%
Thyroid receptor binding	-	0.6650	66.50%
Glucocorticoid receptor binding	-	0.6652	66.52%
Aromatase binding	+	0.5193	51.93%
PPAR gamma	+	0.5465	54.65%
Honey bee toxicity	-	0.8665	86.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	-	0.6700	67.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.64%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.38%	93.40%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	90.09%	98.33%
CHEMBL2581	P07339	Cathepsin D	90.05%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.55%	82.69%
CHEMBL5805	Q9NR97	Toll-like receptor 8	86.63%	96.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.65%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.19%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.34%	99.23%

Plants that contains it

• Anarthrophyllum elegans
• Baptisia australis
• Corydalis incisa
• Cytisus scoparius
• Dermatophyllum secundiflorum
• Dicraeopetalum stipulare
• Euchresta japonica
• Genista acanthoclada
• Genista cinerascens
• Genista lobelii
• Genista maderensis
• Genista tinctoria
• Gonocytisus pterocladus
• Lamprolobium fruticosum
• Lupinus odoratus
• Maackia amurensis
• Maackia hupehensis
• Maackia tashiroi
• Maackia tenuifolia
• Osyris alba
• Pericopsis angolensis
• Petteria ramentacea
• Plagiocarpus axillaris
• Platycelyphium voense
• Retama sphaerocarpa
• Sophora chrysophylla
• Sophora exigua
• Sophora koreensis
• Sophora mollis
• Sophora tonkinensis
• Spartium junceum
• Thermopsis chinensis
• Thermopsis lanceolata
• Ulex europaeus

Cross-Links

• PubChem: 589870
• NPASS: NPC244256
• ChEMBL: CHEMBL1433686
• LOTUS: LTS0240022
• wikiData: Q104252924