(2S)-2-[(2R)-2-hydroxy-1-[(2R)-4-(hydroxymethyl)-5-oxo-2H-furan-2-yl]propan-2-yl]-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one

Details

• Internal ID: fdefc937-4a8b-40a2-a52e-44ea1d752209
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > p-Dioxolo[2,3-h]coumarins
• IUPAC Name: (2S)-2-[(2R)-2-hydroxy-1-[(2R)-4-(hydroxymethyl)-5-oxo-2H-furan-2-yl]propan-2-yl]-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• SMILES (Canonical): CC(CC1C=C(C(=O)O1)CO)(C2COC3=C(O2)C4=C(C=C3)C=CC(=O)O4)O
• SMILES (Isomeric): C[C@@](C[C@@H]1C=C(C(=O)O1)CO)([C@@H]2COC3=C(O2)C4=C(C=C3)C=CC(=O)O4)O
• InChI: InChI=1S/C19H18O8/c1-19(23,7-12-6-11(8-20)18(22)25-12)14-9-24-13-4-2-10-3-5-15(21)27-16(10)17(13)26-14/h2-6,12,14,20,23H,7-9H2,1H3/t12-,14-,19+/m0/s1
• InChI Key: GDPHCYVELMTBIG-PTAUBWNISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.92
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.7595	75.95%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7913	79.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8921	89.21%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7212	72.12%
P-glycoprotein inhibitior	-	0.4724	47.24%
P-glycoprotein substrate	-	0.7035	70.35%
CYP3A4 substrate	+	0.5587	55.87%
CYP2C9 substrate	-	0.6092	60.92%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.7916	79.16%
CYP2C9 inhibition	-	0.8144	81.44%
CYP2C19 inhibition	-	0.7744	77.44%
CYP2D6 inhibition	-	0.8989	89.89%
CYP1A2 inhibition	-	0.7585	75.85%
CYP2C8 inhibition	-	0.6310	63.10%
CYP inhibitory promiscuity	-	0.8578	85.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5032	50.32%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9635	96.35%
Skin irritation	-	0.7326	73.26%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4269	42.69%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.5729	57.29%
skin sensitisation	-	0.8070	80.70%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6905	69.05%
Acute Oral Toxicity (c)	III	0.4156	41.56%
Estrogen receptor binding	+	0.9158	91.58%
Androgen receptor binding	+	0.7238	72.38%
Thyroid receptor binding	-	0.5712	57.12%
Glucocorticoid receptor binding	+	0.8061	80.61%
Aromatase binding	+	0.6922	69.22%
PPAR gamma	+	0.7506	75.06%
Honey bee toxicity	-	0.8199	81.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	94.30%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.14%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.88%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.85%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	87.60%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.98%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.90%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.33%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.57%	100.00%

Plants that contains it

• Clausena excavata

Cross-Links

• PubChem: 162972426
• LOTUS: LTS0029531
• wikiData: Q105006863