(5aS,10bS)-1,3,9-trihydroxy-8,10-dimethoxy-5a-[(2S,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]oxy-10bH-indeno[2,3-b][1]benzofuran-6-one

Details

• Internal ID: ac3109db-7a29-4c45-939f-372677854252
• Taxonomy: Benzenoids > Indanes > Indanones
• IUPAC Name: (5aS,10bS)-1,3,9-trihydroxy-8,10-dimethoxy-5a-[(2S,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]oxy-10bH-indeno[2,3-b][1]benzofuran-6-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC34C(C5=C(C(=C(C=C5C3=O)OC)O)OC)C6=C(C=C(C=C6O4)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@]34[C@@H](C5=C(C(=C(C=C5C3=O)OC)O)OC)C6=C(C=C(C=C6O4)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H34O17/c1-8-18(32)21(35)23(37)27(43-8)42-7-14-19(33)22(36)24(38)28(44-14)46-29-17(16-11(31)4-9(30)5-12(16)45-29)15-10(26(29)39)6-13(40-2)20(34)25(15)41-3/h4-6,8,14,17-19,21-24,27-28,30-38H,7H2,1-3H3/t8-,14+,17-,18-,19+,21+,22-,23+,24+,27+,28-,29-/m0/s1
• InChI Key: GRQAFLHJGNYVJK-HVDMQONLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₇
• Molecular Weight: 654.60 g/mol
• Exact Mass: 654.17959961 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): -2.09
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5397	53.97%
Caco-2	-	0.8892	88.92%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6863	68.63%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.8311	83.11%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6375	63.75%
P-glycoprotein inhibitior	-	0.4863	48.63%
P-glycoprotein substrate	+	0.5214	52.14%
CYP3A4 substrate	+	0.6657	66.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.8275	82.75%
CYP2C9 inhibition	-	0.8658	86.58%
CYP2C19 inhibition	-	0.7950	79.50%
CYP2D6 inhibition	-	0.8859	88.59%
CYP1A2 inhibition	-	0.8254	82.54%
CYP2C8 inhibition	+	0.6553	65.53%
CYP inhibitory promiscuity	-	0.6540	65.40%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5746	57.46%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.8221	82.21%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.5645	56.45%
Human Ether-a-go-go-Related Gene inhibition	-	0.3970	39.70%
Micronuclear	+	0.6792	67.92%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8838	88.38%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8894	88.94%
Acute Oral Toxicity (c)	III	0.6565	65.65%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.6580	65.80%
Thyroid receptor binding	+	0.5555	55.55%
Glucocorticoid receptor binding	+	0.6972	69.72%
Aromatase binding	+	0.6275	62.75%
PPAR gamma	+	0.7124	71.24%
Honey bee toxicity	-	0.7121	71.21%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8655	86.55%

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	99.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.14%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.06%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.79%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.55%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	94.14%	94.75%
CHEMBL2581	P07339	Cathepsin D	93.20%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.85%	95.56%
CHEMBL4208	P20618	Proteasome component C5	89.83%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	87.91%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.06%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.24%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.53%	99.15%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.89%	82.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.67%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.21%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.15%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.94%	96.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.32%	94.80%
CHEMBL1255126	O15151	Protein Mdm4	80.62%	90.20%
CHEMBL1951	P21397	Monoamine oxidase A	80.13%	91.49%

Plants that contains it

• Aconitum variegatum
• Hemionitis pteridioides
• Ostrya carpinifolia
• Stephania dielsiana
• Vangueria agrestis

Cross-Links

• PubChem: 56925408
• NPASS: NPC2556