(4bR,5S,11bS)-1,2-dimethoxy-12-methyl-13-methylidene-4b,5,6,11b-tetrahydro-[1,3]benzodioxolo[5,6-c]phenanthridin-5-ol

Details

• Internal ID: 5da090ed-1589-4418-9f89-fc5c023f5508
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Hexahydrobenzophenanthridine alkaloids
• IUPAC Name: (4bR,5S,11bS)-1,2-dimethoxy-12-methyl-13-methylidene-4b,5,6,11b-tetrahydro-[1,3]benzodioxolo[5,6-c]phenanthridin-5-ol
• SMILES (Canonical): CN1C2C(C(CC3=CC4=C(C=C23)OCO4)O)C5=C(C1=C)C(=C(C=C5)OC)OC
• SMILES (Isomeric): CN1[C@H]2[C@H]([C@H](CC3=CC4=C(C=C23)OCO4)O)C5=C(C1=C)C(=C(C=C5)OC)OC
• InChI: InChI=1S/C22H23NO5/c1-11-19-13(5-6-16(25-3)22(19)26-4)20-15(24)7-12-8-17-18(28-10-27-17)9-14(12)21(20)23(11)2/h5-6,8-9,15,20-21,24H,1,7,10H2,2-4H3/t15-,20-,21+/m0/s1
• InChI Key: WLOSIJXUIVRNQV-ONGXBYRLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₃NO₅
• Molecular Weight: 381.40 g/mol
• Exact Mass: 381.15762283 g/mol
• Topological Polar Surface Area (TPSA): 60.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.09
• 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	+	0.9363	93.63%
Caco-2	+	0.7343	73.43%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4338	43.38%
OATP2B1 inhibitior	-	0.8679	86.79%
OATP1B1 inhibitior	+	0.9191	91.91%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8022	80.22%
P-glycoprotein inhibitior	+	0.7076	70.76%
P-glycoprotein substrate	-	0.6011	60.11%
CYP3A4 substrate	+	0.6132	61.32%
CYP2C9 substrate	-	0.6171	61.71%
CYP2D6 substrate	+	0.5731	57.31%
CYP3A4 inhibition	+	0.8242	82.42%
CYP2C9 inhibition	-	0.7233	72.33%
CYP2C19 inhibition	+	0.7482	74.82%
CYP2D6 inhibition	+	0.6124	61.24%
CYP1A2 inhibition	+	0.6866	68.66%
CYP2C8 inhibition	-	0.6950	69.50%
CYP inhibitory promiscuity	+	0.6281	62.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.3907	39.07%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9316	93.16%
Skin irritation	-	0.7870	78.70%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3942	39.42%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8173	81.73%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7609	76.09%
Acute Oral Toxicity (c)	III	0.6627	66.27%
Estrogen receptor binding	+	0.7875	78.75%
Androgen receptor binding	+	0.6523	65.23%
Thyroid receptor binding	+	0.7180	71.80%
Glucocorticoid receptor binding	+	0.7582	75.82%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7393	73.93%
Honey bee toxicity	-	0.8379	83.79%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8805	88.05%

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	98.41%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.89%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	97.81%	83.82%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.90%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.15%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	92.42%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.46%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.88%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.18%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.86%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.27%	91.11%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	85.55%	94.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.50%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.37%	94.00%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.31%	96.86%
CHEMBL2056	P21728	Dopamine D1 receptor	83.94%	91.00%
CHEMBL4208	P20618	Proteasome component C5	82.96%	90.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.01%	82.38%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	81.69%	80.96%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.52%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.33%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.13%	85.14%

Plants that contains it

• Chelidonium majus

Cross-Links

• PubChem: 101670978
• LOTUS: LTS0051082
• wikiData: Q105308134