(1R,18R,19R,20S)-19-ethenyl-16-hydroxy-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-14-one

Details

• Internal ID: fbdcdda5-5945-47d4-86fc-e526086acecb
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: (1R,18R,19R,20S)-19-ethenyl-16-hydroxy-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-14-one
• SMILES (Canonical): C=CC1C2CC3C4=C(CCN3C(=O)C2=C(OC1OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC=CC=C6N4
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2C[C@@H]3C4=C(CCN3C(=O)C2=C(O[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C6=CC=CC=C6N4
• InChI: InChI=1S/C26H30N2O9/c1-2-11-14-9-16-19-13(12-5-3-4-6-15(12)27-19)7-8-28(16)23(33)18(14)24(34)36-25(11)37-26-22(32)21(31)20(30)17(10-29)35-26/h2-6,11,14,16-17,20-22,25-27,29-32,34H,1,7-10H2/t11-,14+,16-,17-,20-,21+,22-,25+,26+/m1/s1
• InChI Key: OEZCKGRJVNYSLG-RSNGGLKUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀N₂O₉
• Molecular Weight: 514.50 g/mol
• Exact Mass: 514.19513054 g/mol
• Topological Polar Surface Area (TPSA): 165.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7874	78.74%
Caco-2	-	0.8432	84.32%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6856	68.56%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.8351	83.51%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7222	72.22%
P-glycoprotein inhibitior	-	0.5406	54.06%
P-glycoprotein substrate	-	0.5765	57.65%
CYP3A4 substrate	+	0.7084	70.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.7888	78.88%
CYP2C9 inhibition	-	0.8123	81.23%
CYP2C19 inhibition	-	0.8407	84.07%
CYP2D6 inhibition	-	0.8716	87.16%
CYP1A2 inhibition	-	0.6392	63.92%
CYP2C8 inhibition	+	0.5923	59.23%
CYP inhibitory promiscuity	-	0.7045	70.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5714	57.14%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9502	95.02%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6966	69.66%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.6284	62.84%
skin sensitisation	-	0.8577	85.77%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6294	62.94%
Acute Oral Toxicity (c)	III	0.5739	57.39%
Estrogen receptor binding	+	0.8531	85.31%
Androgen receptor binding	+	0.6687	66.87%
Thyroid receptor binding	+	0.5694	56.94%
Glucocorticoid receptor binding	+	0.5498	54.98%
Aromatase binding	+	0.5336	53.36%
PPAR gamma	+	0.6680	66.80%
Honey bee toxicity	-	0.6908	69.08%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8970	89.70%

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	99.22%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.33%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.90%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.77%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.30%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.37%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.96%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.45%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.20%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.81%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	89.76%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.16%	86.92%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.69%	90.08%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.11%	91.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.37%	88.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.04%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.06%	94.00%

Plants that contains it

• Adina racemosa
• Camptotheca acuminata
• Uncaria rhynchophylla

Cross-Links

• PubChem: 44567197
• NPASS: NPC97553