(1R,4R,6S,8aR)-1-(furan-2-yl)-4,6-dihydroxy-5,8a-dimethyl-4,6,7,8-tetrahydro-1H-isochromen-3-one

Details

• Internal ID: ad953e2a-813e-410f-ba36-40b5e21b28b8
• Taxonomy: Organoheterocyclic compounds > Benzopyrans
• IUPAC Name: (1R,4R,6S,8aR)-1-(furan-2-yl)-4,6-dihydroxy-5,8a-dimethyl-4,6,7,8-tetrahydro-1H-isochromen-3-one
• SMILES (Canonical): CC1=C2C(C(=O)OC(C2(CCC1O)C)C3=CC=CO3)O
• SMILES (Isomeric): CC1=C2[C@H](C(=O)O[C@H]([C@@]2(CC[C@@H]1O)C)C3=CC=CO3)O
• InChI: InChI=1S/C15H18O5/c1-8-9(16)5-6-15(2)11(8)12(17)14(18)20-13(15)10-4-3-7-19-10/h3-4,7,9,12-13,16-17H,5-6H2,1-2H3/t9-,12+,13-,15+/m0/s1
• InChI Key: BEESSGBQWOGPBY-BYDSVVRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 79.90 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.72
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	-	0.5775	57.75%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8223	82.23%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9223	92.23%
OATP1B3 inhibitior	+	0.9308	93.08%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9554	95.54%
P-glycoprotein inhibitior	-	0.8979	89.79%
P-glycoprotein substrate	-	0.8634	86.34%
CYP3A4 substrate	+	0.5845	58.45%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.8009	80.09%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8410	84.10%
CYP2C19 inhibition	-	0.8670	86.70%
CYP2D6 inhibition	-	0.8613	86.13%
CYP1A2 inhibition	-	0.6976	69.76%
CYP2C8 inhibition	-	0.8842	88.42%
CYP inhibitory promiscuity	-	0.7644	76.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4632	46.32%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9578	95.78%
Skin irritation	-	0.5210	52.10%
Skin corrosion	-	0.8724	87.24%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4701	47.01%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5180	51.80%
skin sensitisation	-	0.8155	81.55%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4937	49.37%
Acute Oral Toxicity (c)	I	0.4113	41.13%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.7291	72.91%
Glucocorticoid receptor binding	+	0.5694	56.94%
Aromatase binding	-	0.5866	58.66%
PPAR gamma	+	0.5364	53.64%
Honey bee toxicity	-	0.8836	88.36%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9681	96.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.71%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.21%	91.11%
CHEMBL2581	P07339	Cathepsin D	86.60%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.32%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.65%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.50%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.50%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.46%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.46%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.14%	97.14%

Plants that contains it

• Dictamnus dasycarpus

Cross-Links

• PubChem: 163012284
• LOTUS: LTS0148181
• wikiData: Q104932777