(3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 977a238c-e7a4-4448-8c87-ab4bee83be9e
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,3aS,9aS,9bS)-3,6-dimethyl-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1C2CCC(=C3C(C2OC1=O)C(=CC3=O)COC4C(C(C(C(O4)COC5C(C(C(C(O5)C)O)O)O)O)O)O)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CCC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)O)O)O)O)O)O)C
• InChI: InChI=1S/C27H38O13/c1-9-4-5-13-10(2)25(35)40-24(13)17-12(6-14(28)16(9)17)7-36-27-23(34)21(32)19(30)15(39-27)8-37-26-22(33)20(31)18(29)11(3)38-26/h6,10-11,13,15,17-24,26-27,29-34H,4-5,7-8H2,1-3H3/t10-,11-,13-,15+,17-,18-,19+,20+,21-,22+,23+,24-,26+,27+/m0/s1
• InChI Key: AIDJHLWRZXMPHP-NBZSIFSQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₁₃
• Molecular Weight: 570.60 g/mol
• Exact Mass: 570.23124126 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -1.93
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7547	75.47%
Caco-2	-	0.8600	86.00%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7970	79.70%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.8935	89.35%
OATP1B3 inhibitior	+	0.8945	89.45%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6081	60.81%
P-glycoprotein inhibitior	-	0.5741	57.41%
P-glycoprotein substrate	-	0.6106	61.06%
CYP3A4 substrate	+	0.6473	64.73%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.9013	90.13%
CYP3A4 inhibition	-	0.8921	89.21%
CYP2C9 inhibition	-	0.7963	79.63%
CYP2C19 inhibition	-	0.8362	83.62%
CYP2D6 inhibition	-	0.9096	90.96%
CYP1A2 inhibition	-	0.7621	76.21%
CYP2C8 inhibition	-	0.6013	60.13%
CYP inhibitory promiscuity	-	0.8633	86.33%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5662	56.62%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9397	93.97%
Skin irritation	-	0.6342	63.42%
Skin corrosion	-	0.9262	92.62%
Ames mutagenesis	-	0.7108	71.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.4177	41.77%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.8906	89.06%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7774	77.74%
Acute Oral Toxicity (c)	III	0.5960	59.60%
Estrogen receptor binding	+	0.7047	70.47%
Androgen receptor binding	+	0.6237	62.37%
Thyroid receptor binding	-	0.6210	62.10%
Glucocorticoid receptor binding	-	0.4940	49.40%
Aromatase binding	-	0.5113	51.13%
PPAR gamma	+	0.5572	55.72%
Honey bee toxicity	-	0.7941	79.41%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9417	94.17%

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	96.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.27%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.11%	97.36%
CHEMBL2581	P07339	Cathepsin D	91.48%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.61%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.43%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.72%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.04%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.76%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.95%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.89%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.04%	94.80%
CHEMBL3401	O75469	Pregnane X receptor	84.56%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.44%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.46%	99.17%
CHEMBL1871	P10275	Androgen Receptor	81.85%	96.43%
CHEMBL5255	O00206	Toll-like receptor 4	81.33%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.21%	99.23%

Plants that contains it

• Cichorium endivia

Cross-Links

• PubChem: 102476811
• LOTUS: LTS0051848
• wikiData: Q104912663