10-hydroxy-5,7-dimethoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one

Details

• Internal ID: 6f03870e-f3b5-486d-b010-e66b9f21fa2b
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 10-hydroxy-5,7-dimethoxy-3-methyl-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxybenzo[g]isochromen-1-one
• SMILES (Canonical): CC1=CC2=C(C(=C3C(=CC(=CC3=C2OC)OC)OC4C(C(C(C(O4)COC5C(C(C(CO5)O)O)O)O)O)O)O)C(=O)O1
• SMILES (Isomeric): CC1=CC2=C(C(=C3C(=CC(=CC3=C2OC)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO[C@H]5[C@@H]([C@H]([C@H](CO5)O)O)O)O)O)O)O)C(=O)O1
• InChI: InChI=1S/C27H32O15/c1-9-4-11-17(25(35)40-9)20(31)16-12(24(11)37-3)5-10(36-2)6-14(16)41-27-23(34)21(32)19(30)15(42-27)8-39-26-22(33)18(29)13(28)7-38-26/h4-6,13,15,18-19,21-23,26-34H,7-8H2,1-3H3/t13-,15+,18-,19+,21-,22+,23+,26-,27+/m0/s1
• InChI Key: QIZARGSUDZBXDB-JHVBERTJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.17412031 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.38
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5703	57.03%
Caco-2	-	0.8685	86.85%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5905	59.05%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.8478	84.78%
OATP1B3 inhibitior	+	0.9343	93.43%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6462	64.62%
P-glycoprotein inhibitior	-	0.5544	55.44%
P-glycoprotein substrate	-	0.5107	51.07%
CYP3A4 substrate	+	0.6619	66.19%
CYP2C9 substrate	-	0.6766	67.66%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.9546	95.46%
CYP2C9 inhibition	-	0.9698	96.98%
CYP2C19 inhibition	-	0.9420	94.20%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.9104	91.04%
CYP2C8 inhibition	+	0.4478	44.78%
CYP inhibitory promiscuity	-	0.9317	93.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6576	65.76%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9298	92.98%
Skin irritation	-	0.8443	84.43%
Skin corrosion	-	0.9679	96.79%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.6924	69.24%
skin sensitisation	-	0.9135	91.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9758	97.58%
Acute Oral Toxicity (c)	III	0.7255	72.55%
Estrogen receptor binding	+	0.8346	83.46%
Androgen receptor binding	-	0.5146	51.46%
Thyroid receptor binding	+	0.5441	54.41%
Glucocorticoid receptor binding	+	0.6200	62.00%
Aromatase binding	+	0.6395	63.95%
PPAR gamma	+	0.7074	70.74%
Honey bee toxicity	-	0.8115	81.15%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.7679	76.79%

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	99.66%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.51%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.43%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.13%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	92.27%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.04%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.12%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.10%	96.09%
CHEMBL1871	P10275	Androgen Receptor	88.59%	96.43%
CHEMBL3401	O75469	Pregnane X receptor	87.83%	94.73%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.80%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.28%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL4581	P52732	Kinesin-like protein 1	85.57%	93.18%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.39%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	84.88%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.89%	95.89%
CHEMBL2535	P11166	Glucose transporter	83.32%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.81%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.75%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.46%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.64%	95.83%

Plants that contains it

• Paepalanthus microphyllus

Cross-Links

• PubChem: 11082549
• LOTUS: LTS0094212
• wikiData: Q105222485