(2S,4aR,6aR,7R,10aS,10bS)-2-(furan-3-yl)-7-hydroxy-6a,10b-dimethyl-2,4a,5,6,7,10a-hexahydro-1H-benzo[f]isochromene-4,10-dione

Details

• Internal ID: 757342a5-d162-4e25-99c9-82bfd2f2ccd6
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (2S,4aR,6aR,7R,10aS,10bS)-2-(furan-3-yl)-7-hydroxy-6a,10b-dimethyl-2,4a,5,6,7,10a-hexahydro-1H-benzo[f]isochromene-4,10-dione
• SMILES (Canonical): CC12CCC3C(=O)OC(CC3(C1C(=O)C=CC2O)C)C4=COC=C4
• SMILES (Isomeric): C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@]3([C@@H]1C(=O)C=C[C@H]2O)C)C4=COC=C4
• InChI: InChI=1S/C19H22O5/c1-18-7-5-12-17(22)24-14(11-6-8-23-10-11)9-19(12,2)16(18)13(20)3-4-15(18)21/h3-4,6,8,10,12,14-16,21H,5,7,9H2,1-2H3/t12-,14-,15+,16+,18-,19+/m0/s1
• InChI Key: RKUPDDZLTBYXDN-RSDLCGCGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.40 g/mol
• Exact Mass: 330.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.70 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	+	0.5881	58.81%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8343	83.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7081	70.81%
OATP1B3 inhibitior	-	0.2808	28.08%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8358	83.58%
BSEP inhibitior	-	0.7077	70.77%
P-glycoprotein inhibitior	-	0.8423	84.23%
P-glycoprotein substrate	-	0.7137	71.37%
CYP3A4 substrate	+	0.6560	65.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8887	88.87%
CYP3A4 inhibition	-	0.7112	71.12%
CYP2C9 inhibition	-	0.9114	91.14%
CYP2C19 inhibition	-	0.9202	92.02%
CYP2D6 inhibition	-	0.9613	96.13%
CYP1A2 inhibition	-	0.8221	82.21%
CYP2C8 inhibition	-	0.8569	85.69%
CYP inhibitory promiscuity	-	0.9479	94.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5042	50.42%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9801	98.01%
Skin irritation	-	0.5751	57.51%
Skin corrosion	-	0.8355	83.55%
Ames mutagenesis	-	0.7170	71.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7543	75.43%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.8886	88.86%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5963	59.63%
Acute Oral Toxicity (c)	I	0.5683	56.83%
Estrogen receptor binding	+	0.7995	79.95%
Androgen receptor binding	+	0.6067	60.67%
Thyroid receptor binding	-	0.4906	49.06%
Glucocorticoid receptor binding	+	0.6560	65.60%
Aromatase binding	+	0.6989	69.89%
PPAR gamma	-	0.5884	58.84%
Honey bee toxicity	-	0.9025	90.25%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9953	99.53%

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	94.90%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.61%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.42%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.75%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.97%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.02%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.55%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.08%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.87%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.32%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	81.90%	90.17%

Plants that contains it

• Tinospora cordifolia

Cross-Links

• PubChem: 15215479
• LOTUS: LTS0189377
• wikiData: Q105239269