3,5,10,11-tetrahydroxy-9-methoxy-13-[(4-methoxyphenyl)methyl]-13H-naphtho[1,2-b]xanthene-7,14-dione

Details

• Internal ID: 187b848c-e69c-4de0-a7bf-f2d0867d0c13
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 3,5,10,11-tetrahydroxy-9-methoxy-13-[(4-methoxyphenyl)methyl]-13H-naphtho[1,2-b]xanthene-7,14-dione
• SMILES (Canonical): COC1=CC=C(C=C1)CC2C3=CC(=C(C(=C3OC4=C2C(=O)C5=C6C=CC(=CC6=C(C=C5C4=O)O)O)OC)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)CC2C3=CC(=C(C(=C3OC4=C2C(=O)C5=C6C=CC(=CC6=C(C=C5C4=O)O)O)OC)O)O
• InChI: InChI=1S/C30H22O9/c1-37-15-6-3-13(4-7-15)9-18-19-11-22(33)26(35)30(38-2)28(19)39-29-24(18)27(36)23-16-8-5-14(31)10-17(16)21(32)12-20(23)25(29)34/h3-8,10-12,18,31-33,35H,9H2,1-2H3
• InChI Key: MSWPRHPOWDEIGL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₉
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.12638228 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.73
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9517	95.17%
Caco-2	-	0.8204	82.04%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7225	72.25%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8298	82.98%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9116	91.16%
P-glycoprotein inhibitior	+	0.8041	80.41%
P-glycoprotein substrate	+	0.5490	54.90%
CYP3A4 substrate	+	0.6877	68.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7736	77.36%
CYP3A4 inhibition	-	0.6834	68.34%
CYP2C9 inhibition	+	0.7351	73.51%
CYP2C19 inhibition	+	0.7370	73.70%
CYP2D6 inhibition	-	0.6642	66.42%
CYP1A2 inhibition	+	0.7395	73.95%
CYP2C8 inhibition	+	0.8542	85.42%
CYP inhibitory promiscuity	+	0.7510	75.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5958	59.58%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.8022	80.22%
Skin irritation	-	0.7137	71.37%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6943	69.43%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5342	53.42%
skin sensitisation	-	0.7975	79.75%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9058	90.58%
Acute Oral Toxicity (c)	III	0.5035	50.35%
Estrogen receptor binding	+	0.9010	90.10%
Androgen receptor binding	+	0.8073	80.73%
Thyroid receptor binding	+	0.5971	59.71%
Glucocorticoid receptor binding	+	0.7770	77.70%
Aromatase binding	-	0.6208	62.08%
PPAR gamma	+	0.7509	75.09%
Honey bee toxicity	-	0.8040	80.40%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9781	97.81%

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	99.29%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.06%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.00%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.83%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.82%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.30%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.76%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.75%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.65%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.60%	95.89%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	90.43%	96.09%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	89.21%	92.68%
CHEMBL2535	P11166	Glucose transporter	88.46%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.30%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	87.31%	93.18%
CHEMBL3401	O75469	Pregnane X receptor	86.34%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.33%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.73%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.86%	99.23%
CHEMBL1907	P15144	Aminopeptidase N	84.41%	93.31%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.97%	96.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.59%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.41%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.14%	89.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.88%	95.53%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.78%	86.92%

Plants that contains it

• Dendrobium moniliforme

Cross-Links

• PubChem: 44235856
• LOTUS: LTS0218463
• wikiData: Q105171491