(2S,3S,4S,5R,6R)-4,5,6-trihydroxy-15-methoxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,18-diazatetracyclo[9.7.0.02,8.012,17]octadeca-1(11),12(17),13,15-tetraen-7-one

Details

• Internal ID: 5cf4a9a1-8f29-4b88-8873-3696a598be42
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: (2S,3S,4S,5R,6R)-4,5,6-trihydroxy-15-methoxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,18-diazatetracyclo[9.7.0.02,8.012,17]octadeca-1(11),12(17),13,15-tetraen-7-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=C(N2)C4C(C(C(C(C(=O)N4CC3)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C(N2)[C@H]4[C@@H]([C@H]([C@H]([C@H](C(=O)N4CC3)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C23H30N2O11/c1-34-8-2-3-9-10-4-5-25-14(13(10)24-11(9)6-8)21(18(30)17(29)19(31)22(25)33)36-23-20(32)16(28)15(27)12(7-26)35-23/h2-3,6,12,14-21,23-24,26-32H,4-5,7H2,1H3/t12-,14+,15-,16+,17-,18+,19-,20-,21+,23+/m1/s1
• InChI Key: WDPFRGQQVWGXLZ-MWMWEDMNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀N₂O₁₁
• Molecular Weight: 510.50 g/mol
• Exact Mass: 510.18495978 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.12
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6479	64.79%
Caco-2	-	0.8619	86.19%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Nucleus	0.4209	42.09%
OATP2B1 inhibitior	-	0.8526	85.26%
OATP1B1 inhibitior	+	0.8567	85.67%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5984	59.84%
P-glycoprotein inhibitior	-	0.6600	66.00%
P-glycoprotein substrate	-	0.6539	65.39%
CYP3A4 substrate	+	0.6599	65.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8223	82.23%
CYP3A4 inhibition	-	0.8289	82.89%
CYP2C9 inhibition	-	0.7152	71.52%
CYP2C19 inhibition	-	0.7936	79.36%
CYP2D6 inhibition	-	0.7636	76.36%
CYP1A2 inhibition	-	0.7492	74.92%
CYP2C8 inhibition	-	0.7125	71.25%
CYP inhibitory promiscuity	+	0.6190	61.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6593	65.93%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9508	95.08%
Skin irritation	-	0.7903	79.03%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4655	46.55%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6728	67.28%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8655	86.55%
Acute Oral Toxicity (c)	III	0.5931	59.31%
Estrogen receptor binding	+	0.7440	74.40%
Androgen receptor binding	+	0.6418	64.18%
Thyroid receptor binding	-	0.5363	53.63%
Glucocorticoid receptor binding	-	0.5122	51.22%
Aromatase binding	+	0.5791	57.91%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8357	83.57%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8419	84.19%

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	98.66%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.47%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.47%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.20%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.25%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.38%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	91.55%	91.49%
CHEMBL4208	P20618	Proteasome component C5	90.89%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.42%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.20%	86.92%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.80%	85.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.68%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.88%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.83%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.05%	99.17%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	84.08%	85.00%
CHEMBL220	P22303	Acetylcholinesterase	83.38%	94.45%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	82.49%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.12%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.33%	89.00%

Plants that contains it

• Banisteriopsis caapi

Cross-Links

• PubChem: 163193728
• LOTUS: LTS0040754
• wikiData: Q105302576