2-(5,6-Dihydro-9-hydroxy-2-methyl-2,6-methano-2H-1-benzoxocin-4-yl)-5a,10a-dihydro-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-butenyl)-11H-benzofuro[3,2-b][1]benzopyran-11-one

Details

• Internal ID: 6080cd93-2b69-4897-8c22-c905b2ba23a9
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Chromones
• IUPAC Name: 1,3,8,10a-tetrahydroxy-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
• SMILES (Canonical): CC(=CCC12C3=C(C=C(C=C3)O)OC1(C(=O)C4=C(O2)C=C(C(=C4O)C5=CC6(CC(C5)C7=C(O6)C=C(C=C7)O)C)O)O)C
• SMILES (Isomeric): CC(=CCC12C3=C(C=C(C=C3)O)OC1(C(=O)C4=C(O2)C=C(C(=C4O)C5=CC6(CC(C5)C7=C(O6)C=C(C=C7)O)C)O)O)C
• InChI: InChI=1S/C33H30O9/c1-16(2)8-9-32-22-7-5-20(35)12-25(22)42-33(32,39)30(38)28-26(41-32)13-23(36)27(29(28)37)18-10-17-14-31(3,15-18)40-24-11-19(34)4-6-21(17)24/h4-8,11-13,15,17,34-37,39H,9-10,14H2,1-3H3
• InChI Key: GJKQLIDFFREHGO-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₀O₉
• Molecular Weight: 570.60 g/mol
• Exact Mass: 570.18898253 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.53
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• SCHEMBL17523342
• BDBM50377903
• 2-(5,6-Dihydro-9-hydroxy-2-methyl-2,6-methano-2H-1-benzoxocin-4-yl)-5a,10a-dihydro-1,3,8,10a-tetrahydroxy-5a-(3-methyl-2-butenyl)-11H-benzofuro[3,2-b][1]benzopyran-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9773	97.73%
Caco-2	-	0.8064	80.64%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6932	69.32%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8419	84.19%
OATP1B3 inhibitior	-	0.2216	22.16%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9911	99.11%
P-glycoprotein inhibitior	+	0.8343	83.43%
P-glycoprotein substrate	+	0.6922	69.22%
CYP3A4 substrate	+	0.6958	69.58%
CYP2C9 substrate	+	0.5923	59.23%
CYP2D6 substrate	-	0.8095	80.95%
CYP3A4 inhibition	-	0.7039	70.39%
CYP2C9 inhibition	+	0.5532	55.32%
CYP2C19 inhibition	-	0.5285	52.85%
CYP2D6 inhibition	-	0.8822	88.22%
CYP1A2 inhibition	-	0.6880	68.80%
CYP2C8 inhibition	+	0.7614	76.14%
CYP inhibitory promiscuity	+	0.6442	64.42%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5151	51.51%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8633	86.33%
Skin irritation	-	0.6993	69.93%
Skin corrosion	-	0.9279	92.79%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3664	36.64%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.5653	56.53%
skin sensitisation	-	0.7986	79.86%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6766	67.66%
Acute Oral Toxicity (c)	I	0.6262	62.62%
Estrogen receptor binding	+	0.8601	86.01%
Androgen receptor binding	+	0.7984	79.84%
Thyroid receptor binding	+	0.5967	59.67%
Glucocorticoid receptor binding	+	0.8406	84.06%
Aromatase binding	+	0.6866	68.66%
PPAR gamma	+	0.7290	72.90%
Honey bee toxicity	-	0.8002	80.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL221	P23219	Cyclooxygenase-1	42000 nM	IC50	PMID: 16038536

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.82%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.87%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.91%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.83%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.87%	96.09%
CHEMBL236	P41143	Delta opioid receptor	93.01%	99.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.33%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.26%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.49%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.86%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.53%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	88.81%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.73%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.34%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.38%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.60%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.67%	91.38%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.63%	82.38%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.34%	93.40%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.66%	85.11%
CHEMBL217	P14416	Dopamine D2 receptor	81.58%	95.62%
CHEMBL240	Q12809	HERG	80.46%	89.76%
CHEMBL340	P08684	Cytochrome P450 3A4	80.43%	91.19%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.25%	97.50%
CHEMBL301	P24941	Cyclin-dependent kinase 2	80.05%	91.23%

Plants that contains it

• Morus alba
• Morus cathayana
• Morus mongolica

Cross-Links

• PubChem: 44559963
• NPASS: NPC292233
• ChEMBL: CHEMBL507430
• LOTUS: LTS0022385
• wikiData: Q105009448