(19E)-19-ethylidene-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: 5b0f947c-bbb8-4f6d-9036-d751dde4e1f6
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: (19E)-19-ethylidene-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): CC=C1C2CC3C4=C(CCN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)O)C6=CC=CC=C6N4
• SMILES (Isomeric): C/C=C/1\C2CC3C4=C(CCN3C(=O)C2=COC1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC=CC=C6N4
• InChI: InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11,15,18-19,21-23,25-27,29-32H,7-10H2,1H3/b12-2+/t15?,18?,19-,21-,22+,23-,25?,26+/m1/s1
• InChI Key: PICJWPHXKRFPKS-NTOFKXBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀N₂O₈
• Molecular Weight: 498.50 g/mol
• Exact Mass: 498.20021592 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.62
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7690	76.90%
Caco-2	-	0.7897	78.97%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.7445	74.45%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8181	81.81%
OATP1B3 inhibitior	+	0.9253	92.53%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9429	94.29%
P-glycoprotein inhibitior	+	0.5904	59.04%
P-glycoprotein substrate	-	0.5144	51.44%
CYP3A4 substrate	+	0.7125	71.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8391	83.91%
CYP2C9 inhibition	-	0.7967	79.67%
CYP2C19 inhibition	-	0.8328	83.28%
CYP2D6 inhibition	-	0.8643	86.43%
CYP1A2 inhibition	-	0.6315	63.15%
CYP2C8 inhibition	+	0.5908	59.08%
CYP inhibitory promiscuity	-	0.5454	54.54%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5464	54.64%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9751	97.51%
Skin irritation	-	0.7668	76.68%
Skin corrosion	-	0.9356	93.56%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7771	77.71%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.6067	60.67%
skin sensitisation	-	0.8730	87.30%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7825	78.25%
Acute Oral Toxicity (c)	III	0.5999	59.99%
Estrogen receptor binding	+	0.8740	87.40%
Androgen receptor binding	+	0.6981	69.81%
Thyroid receptor binding	+	0.5701	57.01%
Glucocorticoid receptor binding	+	0.6015	60.15%
Aromatase binding	-	0.6249	62.49%
PPAR gamma	+	0.6107	61.07%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8261	82.61%

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	98.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.71%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	96.55%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	96.11%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.54%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.51%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.18%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.20%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.01%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.46%	99.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.84%	95.83%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.34%	85.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.87%	94.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.63%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.19%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.93%	95.89%
CHEMBL5028	O14672	ADAM10	80.27%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.20%	90.08%

Plants that contains it

• Nauclea orientalis

Cross-Links

• PubChem: 5315222
• LOTUS: LTS0146239
• wikiData: Q105209432