(3R,3'S,4'S,4'aS,5'aR)-4'-ethenyl-3'-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[1H-indole-3,6'-4,4a,5,5a,7,8-hexahydro-3H-pyrano[3,4-f]indolizine]-2,10'-dione

Details

• Internal ID: 2d14e8e2-dc57-4c86-bf5f-0c9ff5d03790
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3R,3'S,4'S,4'aS,5'aR)-4'-ethenyl-3'-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[1H-indole-3,6'-4,4a,5,5a,7,8-hexahydro-3H-pyrano[3,4-f]indolizine]-2,10'-dione
• SMILES (Canonical): C=CC1C2CC3C4(CCN3C(=O)C2=COC1OC5C(C(C(C(O5)CO)O)O)O)C6=CC=CC=C6NC4=O
• SMILES (Isomeric): C=C[C@H]1[C@@H]2C[C@@H]3[C@@]4(CCN3C(=O)C2=CO[C@H]1O[C@H]5[C@H]([C@@H]([C@@H]([C@@H](O5)CO)O)O)O)C6=CC=CC=C6NC4=O
• InChI: InChI=1S/C26H30N2O9/c1-2-12-13-9-18-26(15-5-3-4-6-16(15)27-25(26)34)7-8-28(18)22(33)14(13)11-35-23(12)37-24-21(32)20(31)19(30)17(10-29)36-24/h2-6,11-13,17-21,23-24,29-32H,1,7-10H2,(H,27,34)/t12-,13-,17-,18+,19+,20+,21-,23-,24-,26+/m0/s1
• InChI Key: UXDQUMNIWFOBFX-JCWKCVTPSA-N
• Popularity: 0 references 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): 158.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.64
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6316	63.16%
Caco-2	-	0.8534	85.34%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7150	71.50%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8300	83.00%
OATP1B3 inhibitior	+	0.9331	93.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4606	46.06%
P-glycoprotein inhibitior	-	0.4631	46.31%
P-glycoprotein substrate	-	0.5662	56.62%
CYP3A4 substrate	+	0.6901	69.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8559	85.59%
CYP3A4 inhibition	-	0.7723	77.23%
CYP2C9 inhibition	-	0.8280	82.80%
CYP2C19 inhibition	-	0.8859	88.59%
CYP2D6 inhibition	-	0.9099	90.99%
CYP1A2 inhibition	-	0.7578	75.78%
CYP2C8 inhibition	+	0.6465	64.65%
CYP inhibitory promiscuity	-	0.8288	82.88%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4937	49.37%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.9682	96.82%
Skin irritation	-	0.7574	75.74%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6707	67.07%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6341	63.41%
skin sensitisation	-	0.8457	84.57%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7186	71.86%
Acute Oral Toxicity (c)	III	0.5632	56.32%
Estrogen receptor binding	+	0.8501	85.01%
Androgen receptor binding	+	0.7142	71.42%
Thyroid receptor binding	-	0.4938	49.38%
Glucocorticoid receptor binding	+	0.5690	56.90%
Aromatase binding	+	0.5885	58.85%
PPAR gamma	+	0.6837	68.37%
Honey bee toxicity	-	0.7501	75.01%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9481	94.81%

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	97.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.03%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.71%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.47%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.03%	97.09%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.83%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.04%	94.62%
CHEMBL220	P22303	Acetylcholinesterase	89.88%	94.45%
CHEMBL4208	P20618	Proteasome component C5	88.25%	90.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.71%	96.61%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.65%	95.83%
CHEMBL3524	P56524	Histone deacetylase 4	85.96%	92.97%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.01%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.95%	95.89%
CHEMBL1937	Q92769	Histone deacetylase 2	84.73%	94.75%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.39%	94.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.14%	94.45%
CHEMBL228	P31645	Serotonin transporter	81.72%	95.51%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.63%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.99%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.57%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.54%	99.23%

Plants that contains it

• Alangium javanicum

Cross-Links

• PubChem: 162893352
• LOTUS: LTS0163861
• wikiData: Q105280734