(1R)-17-methoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.02,10.05,9.014,19]docosa-2(10),3,5(9),14,16,18-hexaene-11,16-diol

Details

• Internal ID: 44d87ed6-fd65-4ed9-ac24-0e08d4297c53
• Taxonomy: Alkaloids and derivatives > Rhoeadine alkaloids
• IUPAC Name: (1R)-17-methoxy-22-methyl-6,8,12-trioxa-22-azapentacyclo[11.9.0.02,10.05,9.014,19]docosa-2(10),3,5(9),14,16,18-hexaene-11,16-diol
• SMILES (Canonical): CN1CCC2=CC(=C(C=C2C3C1C4=C(C(O3)O)C5=C(C=C4)OCO5)O)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C=C2C3[C@H]1C4=C(C(O3)O)C5=C(C=C4)OCO5)O)OC
• InChI: InChI=1S/C20H21NO6/c1-21-6-5-10-7-15(24-2)13(22)8-12(10)18-17(21)11-3-4-14-19(26-9-25-14)16(11)20(23)27-18/h3-4,7-8,17-18,20,22-23H,5-6,9H2,1-2H3/t17-,18?,20?/m1/s1
• InChI Key: DPRSKEMBOBQDJV-PGYGNJIDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.13688739 g/mol
• Topological Polar Surface Area (TPSA): 80.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7858	78.58%
Caco-2	+	0.7283	72.83%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.3994	39.94%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.9197	91.97%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6266	62.66%
P-glycoprotein inhibitior	-	0.5787	57.87%
P-glycoprotein substrate	-	0.5590	55.90%
CYP3A4 substrate	+	0.6598	65.98%
CYP2C9 substrate	-	0.6090	60.90%
CYP2D6 substrate	+	0.6271	62.71%
CYP3A4 inhibition	-	0.6645	66.45%
CYP2C9 inhibition	-	0.6474	64.74%
CYP2C19 inhibition	+	0.5763	57.63%
CYP2D6 inhibition	-	0.6123	61.23%
CYP1A2 inhibition	-	0.7119	71.19%
CYP2C8 inhibition	-	0.6583	65.83%
CYP inhibitory promiscuity	-	0.6669	66.69%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9662	96.62%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5952	59.52%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8362	83.62%
Acute Oral Toxicity (c)	III	0.7061	70.61%
Estrogen receptor binding	+	0.5388	53.88%
Androgen receptor binding	+	0.5696	56.96%
Thyroid receptor binding	+	0.5814	58.14%
Glucocorticoid receptor binding	+	0.8114	81.14%
Aromatase binding	-	0.6917	69.17%
PPAR gamma	+	0.7343	73.43%
Honey bee toxicity	-	0.8516	85.16%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.6832	68.32%

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	99.14%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.38%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.28%	93.40%
CHEMBL2581	P07339	Cathepsin D	95.17%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.61%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.53%	86.33%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	94.41%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.06%	85.14%
CHEMBL2056	P21728	Dopamine D1 receptor	92.30%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.79%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.26%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.52%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.41%	89.62%
CHEMBL3820	P35557	Hexokinase type IV	85.65%	91.96%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.33%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.04%	94.45%
CHEMBL2535	P11166	Glucose transporter	84.02%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.72%	95.89%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.67%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.77%	90.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	82.35%	96.39%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.27%	92.94%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	81.10%	90.95%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	80.65%	96.86%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.51%	82.38%

Plants that contains it

• Papaver somniferum
• Stephania merrillii

Cross-Links

• PubChem: 5319578
• NPASS: NPC7449