Cytisinicline

Details

• Internal ID: 1ed912cc-e693-436c-85ac-83d01306d919
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: (1R,9S)-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]2CNC[C@@H]1C3=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+/m0/s1
• InChI Key: ANJTVLIZGCUXLD-DTWKUNHWSA-N
• Popularity: 1,715 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

• 485-35-8
• Baptitoxine
• Sophorine
• Cytisinicline
• Cytiton
• Tabex
• Baptitoxin
• Laburnin
• Ulexine
• Ulexin
• (-)-Cytisine
• Cytitone
• Tsitizin
• Tabax
• Cystisine
• Citizin
• Cytisin
• Cytizin
• Baphitoxine
• 6039 Sopharma
• (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
• (1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One
• HSDB 3560
• EINECS 207-616-0
• Cytisine (-)
• NSC 407282
• NSC-407282
• UNII-53S5U404NU
• BRN 0083882
• Cytisinicline [USAN]
• 53S5U404NU
• CHEBI:4055
• CHEMBL497939
• 5-24-02-00535 (Beilstein Handbook Reference)
• (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• CYTISINE (MART.)
• CYTISINE [MART.]
• 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-
• 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
• 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
• (1R,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one
• 1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one
• (1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO-(1,2-A)(1,5)DIAZOCIN-8-ONE
• (1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE)
• SMR001233264
• MLS003171607
• citisiniclina
• cytisiniclinum
• MFCD00136048
• NSC407282
• (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one
• Cytisine- Bio-X
• C5E
• Prestwick_140
• Cytisine ((+)-)
• Tocris-1390
• CYTISINE [HSDB]
• CYTISINE [MI]
• Prestwick3_000624
• D08XPW
• CYTISINICLINE [INN]
• (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-Methano-8H-Pyrido[1,2-A][1,5]Diazocin-8-One
• BSPBio_000588
• Cytisine, >=99%, powder
• MLS002153916
• MLS002222174
• SCHEMBL161398
• CYTISINICLINE [WHO-DD]
• BPBio1_000648
• GTPL5347
• (1R,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
• (1S,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
• DTXSID00883395
• 1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine)
• ANJTVLIZGCUXLD-DTWKUNHWSA-N
• Cytisine1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
• HMS2096N10
• HMS2235L06
• HMS3267D20
• HMS3414N03
• HMS3678L21
• HMS3884L11
• HY-N0175
• TNP00030
• BDBM50143282
• HB2033
• PDSP1_000461
• s2287
• WLN: T C666 A GVN LM&TTJ
• AKOS000276818
• AKOS015833102
• CCG-208621
• DB09028
• (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one
• NCGC00016463-01
• NCGC00016463-02
• NCGC00016463-03
• NCGC00016463-04
• NCGC00017171-01
• NCGC00025138-01
• NCGC00025138-02
• NCGC00179513-01
• AC-34317
• AS-19539
• BC164343
• CAS-485-35-8
• LS-59087
• CS-0007888
• SW219952-1
• Cytisine, >=99.0% (HPLC), >=99%
• EN300-224852
• Q417343
• BRD-K74186897-001-02-5
• BRD-K74186897-001-04-1
• BRD-K74186897-001-13-2
• F9994-5373
• Z1203159860
• 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-
• 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R)-
• (1R,9S)-7,11-diazatricyclo[7.3.1.0,2,7]trideca-2,4-dien-6-one
• (1R,9S)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
• 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R-cis)-
• (1R,5S)-1,2,3,4,5,6-hexahydro-1,5-m ethano-8H-pyrido[1,2-a][1,5]diazocin-8-one
• (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
• 115051-74-6

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
CHEMBL3356	P05177	Cytochrome P450 1A2	31622.78 nM	AC50	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	44668.4 nM	Potency	via CMAUP
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	4200 nM; 5890 nM; 1420 nM	Ki; Ki; Ki	PMID: 15908213; PMID: 24901260; PMID: 16171993
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; 63.1 nM	Potency; Potency	via Super-PRED; via CMAUP

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

• Amaranthus spinosus
• Ammodendron karelinii
• Anagyris foetida
• Baptisia australis
• Baptisia tinctoria
• Clathrotropis brachypetala
• Clathrotropis glaucophylla
• Euchresta japonica
• Genista anatolica
• Genista monspessulana
• Heliotropium hirsutissimum
• Inulanthera calva
• Laburnum anagyroidis
• Maackia amurensis
• Maackia hupehensis
• Maackia tashiroi
• Maackia tenuifolia
• Nicotiana raimondii
• Pericopsis angolensis
• Petteria ramentacea
• Piper dilatatum
• Retama raetam
• Scolopia chinensis
• Sophora alopecuroides
• Sophora chrysophylla
• Sophora davidii
• Sophora exigua
• Sophora flavescens
• Sophora franchetiana
• Sophora koreensis
• Sophora tomentosa
• Sophora tonkinensis
• Spartium junceum
• Thermopsis alterniflora
• Thermopsis dolichocarpa
• Thermopsis lanceolata
• Trollius europaeus
• Ulex europaeus

Cross-Links

• PubChem: 10235
• NPASS: NPC77890
• ChEMBL: CHEMBL497939
• LOTUS: LTS0139944
• wikiData: Q417343