1H-Pyrrolo[3,2,1-de]phenanthridine-1,9-diol, 2,4,5,7,11b,11c-hexahydro-10-methoxy-, 1-acetate, (1R,11bS,11cS)-

Details

• Internal ID: c4702b7e-7546-4dab-b0f4-afc822f53a87
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Phenanthridines and derivatives
• IUPAC Name: (5-hydroxy-4-methoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-2,4,6,12-tetraen-15-yl) acetate
• SMILES (Canonical): CC(=O)OC1CC=C2CCN3C2C1C4=CC(=C(C=C4C3)O)OC
• SMILES (Isomeric): CC(=O)OC1CC=C2CCN3C2C1C4=CC(=C(C=C4C3)O)OC
• InChI: InChI=1S/C18H21NO4/c1-10(20)23-15-4-3-11-5-6-19-9-12-7-14(21)16(22-2)8-13(12)17(15)18(11)19/h3,7-8,15,17-18,21H,4-6,9H2,1-2H3
• InChI Key: LSBMSYLHJUUWMU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.40 g/mol
• Exact Mass: 315.14705815 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1H-Pyrrolo[3,2,1-de]phenanthridine-1,9-diol, 2,4,5,7,11b,11c-hexahydro-10-methoxy-, 1-acetate, (1R,11bS,11cS)-
• 1-O-Acetyl-9-O-demethylpluviine
• LSBMSYLHJUUWMU-UHFFFAOYSA-N
• (1R,3a1S,11bS)-9-Hydroxy-10-methoxy-2,3a1,4,5,7,11b-hexahydro-1H-pyrrolo[3,2,1-de]phenanthridin-1-yl acetate
• (5-Hydroxy-4-methoxy-9-azatetracyclo[7.6.1.02,7.012,16]hexadeca-2,4,6,12-tetraen-15-yl) acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9493	94.93%
Caco-2	+	0.8882	88.82%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8730	87.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9223	92.23%
OATP1B3 inhibitior	+	0.9305	93.05%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.7217	72.17%
P-glycoprotein inhibitior	-	0.7661	76.61%
P-glycoprotein substrate	+	0.5069	50.69%
CYP3A4 substrate	+	0.6349	63.49%
CYP2C9 substrate	-	0.8071	80.71%
CYP2D6 substrate	+	0.4531	45.31%
CYP3A4 inhibition	-	0.8719	87.19%
CYP2C9 inhibition	-	0.8894	88.94%
CYP2C19 inhibition	-	0.7667	76.67%
CYP2D6 inhibition	+	0.7049	70.49%
CYP1A2 inhibition	-	0.5413	54.13%
CYP2C8 inhibition	-	0.6197	61.97%
CYP inhibitory promiscuity	-	0.6994	69.94%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5255	52.55%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9278	92.78%
Skin irritation	-	0.7660	76.60%
Skin corrosion	-	0.9389	93.89%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4023	40.23%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8474	84.74%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6676	66.76%
Acute Oral Toxicity (c)	III	0.5944	59.44%
Estrogen receptor binding	-	0.6370	63.70%
Androgen receptor binding	-	0.5250	52.50%
Thyroid receptor binding	-	0.5773	57.73%
Glucocorticoid receptor binding	+	0.7414	74.14%
Aromatase binding	-	0.7829	78.29%
PPAR gamma	+	0.5505	55.05%
Honey bee toxicity	-	0.7939	79.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6104	61.04%
Fish aquatic toxicity	+	0.8618	86.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.23%	85.14%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.94%	91.79%
CHEMBL217	P14416	Dopamine D2 receptor	89.60%	95.62%
CHEMBL340	P08684	Cytochrome P450 3A4	89.56%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.39%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.22%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.21%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.96%	94.45%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.06%	97.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.71%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.30%	95.89%
CHEMBL3820	P35557	Hexokinase type IV	84.75%	91.96%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.69%	90.24%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.77%	89.62%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	82.72%	96.86%
CHEMBL2535	P11166	Glucose transporter	81.01%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.89%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.79%	91.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.22%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.00%	94.00%

Plants that contains it

• Ammocharis coranica
• Brunsvigia radulosa
• Pancratium canariense

Cross-Links

• PubChem: 13918925
• LOTUS: LTS0042214
• wikiData: Q105156459