(1S,12S)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-15-ol

Details

• Internal ID: 04bd1fd2-bac5-470e-9359-aef6c042130b
• Taxonomy: Alkaloids and derivatives > Pavine alkaloids
• IUPAC Name: (1S,12S)-16-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-15-ol
• SMILES (Canonical): CN1C2CC3=CC4=C(C=C3C1CC5=CC(=C(C=C25)O)OC)OCO4
• SMILES (Isomeric): CN1[C@H]2CC3=CC4=C(C=C3[C@@H]1CC5=CC(=C(C=C25)O)OC)OCO4
• InChI: InChI=1S/C19H19NO4/c1-20-14-4-11-6-18-19(24-9-23-18)8-13(11)15(20)3-10-5-17(22-2)16(21)7-12(10)14/h5-8,14-15,21H,3-4,9H2,1-2H3/t14-,15-/m0/s1
• InChI Key: TZJNFQHUSMXCIT-GJZGRUSLSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.40 g/mol
• Exact Mass: 325.13140809 g/mol
• Topological Polar Surface Area (TPSA): 51.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• CHEMBL480663
• (?)-Isocaryachine
• BDBM50259678

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9607	96.07%
Caco-2	+	0.8553	85.53%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.3906	39.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7523	75.23%
P-glycoprotein inhibitior	-	0.5425	54.25%
P-glycoprotein substrate	-	0.7894	78.94%
CYP3A4 substrate	+	0.5269	52.69%
CYP2C9 substrate	-	0.6106	61.06%
CYP2D6 substrate	+	0.6924	69.24%
CYP3A4 inhibition	+	0.6209	62.09%
CYP2C9 inhibition	-	0.8259	82.59%
CYP2C19 inhibition	+	0.6995	69.95%
CYP2D6 inhibition	+	0.7742	77.42%
CYP1A2 inhibition	+	0.7274	72.74%
CYP2C8 inhibition	-	0.8938	89.38%
CYP inhibitory promiscuity	+	0.6130	61.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5721	57.21%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.7776	77.76%
Skin corrosion	-	0.9524	95.24%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5803	58.03%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8558	85.58%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.6542	65.42%
Acute Oral Toxicity (c)	III	0.6960	69.60%
Estrogen receptor binding	+	0.8303	83.03%
Androgen receptor binding	-	0.5855	58.55%
Thyroid receptor binding	+	0.6917	69.17%
Glucocorticoid receptor binding	+	0.8337	83.37%
Aromatase binding	-	0.4925	49.25%
PPAR gamma	+	0.8304	83.04%
Honey bee toxicity	-	0.8392	83.92%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8840	88.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL214	P08908	Serotonin 1a (5-HT1a) receptor	9000 nM	EC50	PMID: 16562853

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.39%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.34%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	95.21%	89.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.30%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.10%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.56%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.23%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.42%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.39%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.57%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	87.47%	88.48%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.89%	99.17%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.15%	82.67%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.83%	95.89%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.22%	96.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.23%	90.71%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.52%	80.96%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	81.99%	99.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.66%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.15%	89.50%
CHEMBL217	P14416	Dopamine D2 receptor	80.77%	95.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.40%	93.99%

Plants that contains it

• Andira surinamensis
• Aralia hispida
• Baeckea frutescens
• Balanophora polyandra
• Boeberastrum anthemidifolium
• Chenopodiastrum murale
• Chenopodium quinoa
• Citrus medica
• Coprosma foetidissima
• Cryptocarya chinensis
• Davidsonia pruriens
• Echinochloa crus-galli
• Eriocephalus kingesii
• Eschscholzia californica
• Geranium collinum
• Girgensohnia oppositiflora
• Harpullia cupanioides
• Isodon eriocalyx
• Lilium pomponium
• Lychnophora pinaster
• Marrubium parviflorum
• Microglossa pyrifolia
• Parthenium confertum
• Polygonatum orientale
• Psathyrotes ramosissima
• Scleropyrum pentandrum
• Selliguea hastata
• Trifolium diffusum
• Veronica stricta
• Youngia japonica
• Zanthoxylum acuminatum subsp. juniperinum

Cross-Links

• PubChem: 44575219
• NPASS: NPC111485
• ChEMBL: CHEMBL480663
• LOTUS: LTS0178491
• wikiData: Q104396832