(1R,12S)-15,16-dimethoxy-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-1-ol

Details

• Internal ID: 380f7700-7c09-4f80-89b5-17b1b78894bd
• Taxonomy: Alkaloids and derivatives > Pavine alkaloids
• IUPAC Name: (1R,12S)-15,16-dimethoxy-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-1-ol
• SMILES (Canonical): CN1C2CC3=CC4=C(C=C3C1(CC5=CC(=C(C=C25)OC)OC)O)OCO4
• SMILES (Isomeric): CN1[C@H]2CC3=CC4=C(C=C3[C@@]1(CC5=CC(=C(C=C25)OC)OC)O)OCO4
• InChI: InChI=1S/C20H21NO5/c1-21-15-4-11-5-18-19(26-10-25-18)8-14(11)20(21,22)9-12-6-16(23-2)17(24-3)7-13(12)15/h5-8,15,22H,4,9-10H2,1-3H3/t15-,20+/m0/s1
• InChI Key: VUKPRDVYZZFSQO-MGPUTAFESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.40 g/mol
• Exact Mass: 355.14197277 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8706	87.06%
Caco-2	+	0.9005	90.05%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.5387	53.87%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.9042	90.42%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6266	62.66%
P-glycoprotein inhibitior	+	0.6300	63.00%
P-glycoprotein substrate	-	0.6818	68.18%
CYP3A4 substrate	+	0.6113	61.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4277	42.77%
CYP3A4 inhibition	-	0.5358	53.58%
CYP2C9 inhibition	-	0.8085	80.85%
CYP2C19 inhibition	-	0.6464	64.64%
CYP2D6 inhibition	-	0.6747	67.47%
CYP1A2 inhibition	-	0.6975	69.75%
CYP2C8 inhibition	-	0.8067	80.67%
CYP inhibitory promiscuity	-	0.6758	67.58%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5784	57.84%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.8057	80.57%
Skin irritation	-	0.7914	79.14%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5595	55.95%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5634	56.34%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.8325	83.25%
Androgen receptor binding	+	0.5719	57.19%
Thyroid receptor binding	+	0.7808	78.08%
Glucocorticoid receptor binding	+	0.7962	79.62%
Aromatase binding	-	0.5354	53.54%
PPAR gamma	+	0.8081	80.81%
Honey bee toxicity	-	0.7560	75.60%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.7452	74.52%

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	98.43%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.94%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.87%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.52%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.20%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.79%	89.62%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.67%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.91%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.75%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.68%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	83.01%	95.62%
CHEMBL2581	P07339	Cathepsin D	82.91%	98.95%
CHEMBL3438	Q05513	Protein kinase C zeta	82.48%	88.48%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.49%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.46%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.26%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.97%	89.50%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.73%	82.38%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.31%	90.95%

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
• 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: 10948236
• NPASS: NPC159082
• LOTUS: LTS0192192
• wikiData: Q105223367