Caulophylline

Details

• Internal ID: b5d71fad-56ad-4869-9061-a0597cf9bc32
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Cytisine and derivatives
• IUPAC Name: (1R,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
• SMILES (Canonical): CN1CC2CC(C1)C3=CC=CC(=O)N3C2
• SMILES (Isomeric): CN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
• InChI: InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9-,10+/m0/s1
• InChI Key: CULUKMPMGVXCEI-VHSXEESVSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆N₂O
• Molecular Weight: 204.27 g/mol
• Exact Mass: 204.126263138 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.90
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Caulophylline
• 486-86-2
• (-)-N-methylcytisine
• 12-Methylcytisine
• UNII-TT0MW69NCI
• TT0MW69NCI
• Methylcytisine
• CHEMBL1085045
• 1,5-Methano-8H-pyrido(1,2a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-3-methyl-, (1R)-
• 5-24-02-00538 (Beilstein Handbook Reference)
• CYTISINE, 12-METHYL-
• 3-Methylcytisine
• EINECS 207-643-8
• BRN 0012448
• CYTISINE, N-METHYL-
• (1R)-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-3-methyl-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
• METHYLCYTISINE [MI]
• N-Methylcytisine, AldrichCPR
• SCHEMBL564472
• (1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
• 1,5-METHANO-8H-PYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE, 1,2,3,4,5,6-HEXAHYDRO-3-METHYL-, (1R,5S)-
• HY-N0443
• BDBM50482164
• MFCD00211091
• N-Methylcytisine, >=98% (HPLC)
• NSC 34656
• AKOS000276920
• AC-34329
• AS-77797
• CS-0008977
• FT-0671641
• (1R,5S)-3-Methyl-3,4,5,6-tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.8839	88.39%
Blood Brain Barrier	+	0.9567	95.67%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7311	73.11%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.9641	96.41%
OATP1B3 inhibitior	+	0.9520	95.20%
MATE1 inhibitior	+	0.6000	60.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8581	85.81%
P-glycoprotein inhibitior	-	0.9786	97.86%
P-glycoprotein substrate	-	0.7079	70.79%
CYP3A4 substrate	+	0.5315	53.15%
CYP2C9 substrate	-	0.8134	81.34%
CYP2D6 substrate	-	0.6893	68.93%
CYP3A4 inhibition	-	0.6687	66.87%
CYP2C9 inhibition	-	0.9184	91.84%
CYP2C19 inhibition	-	0.9010	90.10%
CYP2D6 inhibition	-	0.8771	87.71%
CYP1A2 inhibition	-	0.6270	62.70%
CYP2C8 inhibition	-	0.9780	97.80%
CYP inhibitory promiscuity	+	0.5957	59.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6940	69.40%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.8969	89.69%
Skin irritation	-	0.7344	73.44%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5570	55.70%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6554	65.54%
skin sensitisation	-	0.8387	83.87%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6320	63.20%
Acute Oral Toxicity (c)	III	0.6078	60.78%
Estrogen receptor binding	-	0.7628	76.28%
Androgen receptor binding	-	0.5820	58.20%
Thyroid receptor binding	-	0.5219	52.19%
Glucocorticoid receptor binding	-	0.7766	77.66%
Aromatase binding	-	0.6254	62.54%
PPAR gamma	-	0.5895	58.95%
Honey bee toxicity	-	0.9395	93.95%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	-	0.6641	66.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.41%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.68%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.90%	95.56%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.23%	96.25%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	86.65%	98.33%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.41%	82.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.77%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.79%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.38%	93.40%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.32%	93.99%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clathrotropis glaucophylla
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Genista monspessulana
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Maackia amurensis
• Maackia hupehensis
• Maackia tenuifolia
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Petteria ramentacea
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora chrysophylla
• Sophora flavescens
• Sophora koreensis
• Sophora tonkinensis
• Spartium junceum
• Stenocereus laevigatus
• Syzygium polycephaloides
• Ulex europaeus
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 670971
• NPASS: NPC214125
• ChEMBL: CHEMBL1085045
• LOTUS: LTS0201115
• wikiData: Q27290285