(1S,18S,19S,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2(11),4,6,8,15-pentaene-10,14-dione

Details

• Internal ID: bff7b968-903c-458a-801f-5f06c231ddac
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: (1S,18S,19S,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2(11),4,6,8,15-pentaene-10,14-dione
• SMILES (Canonical): C=CC1C2CC3C4=C(CN3C(=O)C2=COC1OC5C(C(C(C(O5)O)O)O)O)C(=O)C6=CC=CC=C6N4
• SMILES (Isomeric): C=C[C@H]1[C@@H]2C[C@H]3C4=C(CN3C(=O)C2=CO[C@H]1O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)O)O)O)O)C(=O)C6=CC=CC=C6N4
• InChI: InChI=1S/C25H26N2O9/c1-2-10-12-7-16-17-13(18(28)11-5-3-4-6-15(11)26-17)8-27(16)22(32)14(12)9-34-24(10)36-25-21(31)19(29)20(30)23(33)35-25/h2-6,9-10,12,16,19-21,23-25,29-31,33H,1,7-8H2,(H,26,28)/t10-,12-,16-,19-,20-,21+,23-,24-,25-/m0/s1
• InChI Key: UFBOMADLIBHVPD-YOCPMGRGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆N₂O₉
• Molecular Weight: 498.50 g/mol
• Exact Mass: 498.16383041 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.25
• H-Bond Acceptor: 9
• 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	+	0.8310	83.10%
Caco-2	-	0.8198	81.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5522	55.22%
OATP2B1 inhibitior	-	0.8509	85.09%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7657	76.57%
P-glycoprotein inhibitior	-	0.4552	45.52%
P-glycoprotein substrate	-	0.5627	56.27%
CYP3A4 substrate	+	0.7021	70.21%
CYP2C9 substrate	-	0.6038	60.38%
CYP2D6 substrate	-	0.8555	85.55%
CYP3A4 inhibition	-	0.7430	74.30%
CYP2C9 inhibition	-	0.7716	77.16%
CYP2C19 inhibition	-	0.8052	80.52%
CYP2D6 inhibition	-	0.8417	84.17%
CYP1A2 inhibition	-	0.5866	58.66%
CYP2C8 inhibition	+	0.6690	66.90%
CYP inhibitory promiscuity	-	0.6964	69.64%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5525	55.25%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9593	95.93%
Skin irritation	-	0.7674	76.74%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3800	38.00%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.5236	52.36%
skin sensitisation	-	0.8575	85.75%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5787	57.87%
Acute Oral Toxicity (c)	III	0.5476	54.76%
Estrogen receptor binding	+	0.7932	79.32%
Androgen receptor binding	+	0.6987	69.87%
Thyroid receptor binding	+	0.6011	60.11%
Glucocorticoid receptor binding	+	0.5980	59.80%
Aromatase binding	+	0.5236	52.36%
PPAR gamma	+	0.6415	64.15%
Honey bee toxicity	-	0.7170	71.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9891	98.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.19%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.03%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.11%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.75%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.66%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.63%	96.09%
CHEMBL4302	P08183	P-glycoprotein 1	92.55%	92.98%
CHEMBL2581	P07339	Cathepsin D	91.85%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.20%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.52%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.85%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.77%	86.92%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.79%	88.56%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.84%	85.00%
CHEMBL255	P29275	Adenosine A2b receptor	82.04%	98.59%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.72%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.53%	95.89%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.52%	95.56%

Plants that contains it

• Nauclea orientalis

Cross-Links

• PubChem: 161074405
• LOTUS: LTS0000072
• wikiData: Q105271348