Ocoteine

Details

• Internal ID: bab4c798-69b0-4373-9f3a-f3f9c03929ff
• Taxonomy: Alkaloids and derivatives > Aporphines
• IUPAC Name: (12S)-7,16,17-trimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1,6,8(20),14,16,18-hexaene
• SMILES (Canonical): CN1CCC2=C3C1CC4=CC(=C(C=C4C3=C5C(=C2OC)OCO5)OC)OC
• SMILES (Isomeric): CN1CCC2=C3[C@@H]1CC4=CC(=C(C=C4C3=C5C(=C2OC)OCO5)OC)OC
• InChI: InChI=1S/C21H23NO5/c1-22-6-5-12-17-14(22)7-11-8-15(23-2)16(24-3)9-13(11)18(17)20-21(19(12)25-4)27-10-26-20/h8-9,14H,5-7,10H2,1-4H3/t14-/m0/s1
• InChI Key: XEZKWYLHAOYOCL-AWEZNQCLSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.40 g/mol
• Exact Mass: 369.15762283 g/mol
• Topological Polar Surface Area (TPSA): 49.40 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• Talicmine
• 1,2-Methylenedioxy-3,9,10-trimethoxyaporphine
• 73791-37-4
• APORPHINE, 1,2-METHYLENEDIOXY-3,9,10-TRIMETHOXY-
• CHEMBL443099
• 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-4,10,11-trimethoxy-7-methyl-
• LS-21482
• (12S)-7,16,17-trimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1,6,8(20),14,16,18-hexaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9181	91.81%
Caco-2	+	0.9584	95.84%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.5291	52.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9156	91.56%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7681	76.81%
P-glycoprotein inhibitior	-	0.5881	58.81%
P-glycoprotein substrate	-	0.6445	64.45%
CYP3A4 substrate	+	0.6277	62.77%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	+	0.7342	73.42%
CYP3A4 inhibition	+	0.6494	64.94%
CYP2C9 inhibition	-	0.8319	83.19%
CYP2C19 inhibition	+	0.5083	50.83%
CYP2D6 inhibition	+	0.5472	54.72%
CYP1A2 inhibition	-	0.7006	70.06%
CYP2C8 inhibition	-	0.7531	75.31%
CYP inhibitory promiscuity	-	0.6068	60.68%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5767	57.67%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9466	94.66%
Skin irritation	-	0.8092	80.92%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	+	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6894	68.94%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	-	0.6699	66.99%
skin sensitisation	-	0.8666	86.66%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7706	77.06%
Acute Oral Toxicity (c)	III	0.7211	72.11%
Estrogen receptor binding	+	0.6579	65.79%
Androgen receptor binding	-	0.5812	58.12%
Thyroid receptor binding	+	0.6119	61.19%
Glucocorticoid receptor binding	+	0.8187	81.87%
Aromatase binding	-	0.5930	59.30%
PPAR gamma	+	0.5816	58.16%
Honey bee toxicity	-	0.8012	80.12%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.9338	93.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL5747	Q92793	CREB-binding protein	97.07%	95.12%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.80%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.57%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.64%	95.56%
CHEMBL2056	P21728	Dopamine D1 receptor	91.38%	91.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	90.34%	82.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.96%	86.33%
CHEMBL261	P00915	Carbonic anhydrase I	89.88%	96.76%
CHEMBL4208	P20618	Proteasome component C5	89.18%	90.00%
CHEMBL2581	P07339	Cathepsin D	88.74%	98.95%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	88.53%	82.38%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.45%	96.86%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	86.30%	95.53%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	85.39%	92.38%
CHEMBL2535	P11166	Glucose transporter	85.39%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.26%	92.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.06%	90.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.48%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	84.31%	95.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.08%	89.62%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.95%	91.79%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.94%	92.94%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.78%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.29%	94.00%
CHEMBL3438	Q05513	Protein kinase C zeta	83.02%	88.48%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.72%	89.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.68%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.45%	95.89%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	82.23%	95.34%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.95%	95.78%
CHEMBL6031	Q9H9B1	Histone-lysine N-methyltransferase, H3 lysine-9 specific 5	80.89%	94.33%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.73%	99.18%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.01%	91.03%

Plants that contains it

• Cassytha filiformis
• Ocotea acutifolia
• Ocotea puberula
• Ocotea velloziana
• Thalictrum delavayi
• Thalictrum hernandezii
• Thalictrum isopyroides
• Thalictrum minus
• Thalictrum simplex

Cross-Links

• PubChem: 52499
• NPASS: NPC149090
• ChEMBL: CHEMBL443099
• LOTUS: LTS0149019
• wikiData: Q76003384