(2R)-6',10-Dihydroxy-7',9'-dimethoxy-4',5',9-trioxo-4,4',5',9-tetrahydrospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[1,2-b]furan]-7-carboxylic acid methyl ester

Details

• Internal ID: 064c3a98-aa1d-4eaf-9c66-5e9c343d21f9
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Pyranochromenes
• IUPAC Name: methyl (2R)-6',10-dihydroxy-7',9'-dimethoxy-4',5',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[g][1]benzofuran]-7-carboxylate
• SMILES (Canonical): COC1=CC(=C(C2=C1C3=C(CC4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)C(=O)C2=O)O)OC
• SMILES (Isomeric): COC1=CC(=C(C2=C1C3=C(C[C@@]4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)C(=O)C2=O)O)OC
• InChI: InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)24-12(19(28)21(18)30)9-27(39-24)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)22(31)23(10)38-27/h6-8,29,31H,4-5,9H2,1-3H3/t27-/m0/s1
• InChI Key: XJHXEXQIVULOSF-MHZLTWQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₀O₁₂
• Molecular Weight: 536.40 g/mol
• Exact Mass: 536.09547607 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9130	91.30%
Caco-2	-	0.7561	75.61%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8585	85.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8255	82.55%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9252	92.52%
P-glycoprotein inhibitior	+	0.7201	72.01%
P-glycoprotein substrate	+	0.5356	53.56%
CYP3A4 substrate	+	0.6780	67.80%
CYP2C9 substrate	+	0.6272	62.72%
CYP2D6 substrate	-	0.8565	85.65%
CYP3A4 inhibition	-	0.6126	61.26%
CYP2C9 inhibition	-	0.7026	70.26%
CYP2C19 inhibition	-	0.6307	63.07%
CYP2D6 inhibition	-	0.8153	81.53%
CYP1A2 inhibition	+	0.5155	51.55%
CYP2C8 inhibition	+	0.6446	64.46%
CYP inhibitory promiscuity	-	0.5587	55.87%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.6827	68.27%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.8607	86.07%
Skin irritation	-	0.7355	73.55%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4633	46.33%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.5174	51.74%
skin sensitisation	-	0.8261	82.61%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8395	83.95%
Acute Oral Toxicity (c)	I	0.4997	49.97%
Estrogen receptor binding	+	0.8013	80.13%
Androgen receptor binding	+	0.7382	73.82%
Thyroid receptor binding	+	0.5241	52.41%
Glucocorticoid receptor binding	+	0.8867	88.67%
Aromatase binding	+	0.7145	71.45%
PPAR gamma	+	0.7214	72.14%
Honey bee toxicity	-	0.7990	79.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9830	98.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.82%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.84%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.73%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.57%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.15%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.11%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.66%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.97%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	90.12%	94.42%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.86%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.88%	95.56%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.10%	96.67%
CHEMBL4208	P20618	Proteasome component C5	85.90%	90.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.77%	96.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.25%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.77%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.83%	95.89%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	82.52%	91.79%
CHEMBL2535	P11166	Glucose transporter	81.84%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.59%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	81.49%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.80%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.49%	89.00%

Plants that contains it

• Allium ampeloprasum
• Artemisia gmelinii
• Drimia altissima
• Helenium amarum
• Scutellaria viscidula
• Senecio retrorsus
• Taxus wallichiana

Cross-Links

• PubChem: 97042233
• NPASS: NPC85728