(2S,3S)-3-hydroxy-6-methoxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione

Details

• Internal ID: d0542a2b-4b4e-422b-b4bc-1f5f2bc549c3
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (2S,3S)-3-hydroxy-6-methoxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzofuran-4,9-dione
• SMILES (Canonical): CC(=C)C1C(C2=C(O1)C(=O)C3=C(C2=O)C=C(C=C3)OC)O
• SMILES (Isomeric): CC(=C)[C@H]1[C@H](C2=C(O1)C(=O)C3=C(C2=O)C=C(C=C3)OC)O
• InChI: InChI=1S/C16H14O5/c1-7(2)15-14(19)11-12(17)10-6-8(20-3)4-5-9(10)13(18)16(11)21-15/h4-6,14-15,19H,1H2,2-3H3/t14-,15-/m0/s1
• InChI Key: ARZZPZBOYVGESN-GJZGRUSLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.7020	70.20%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7514	75.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9281	92.81%
OATP1B3 inhibitior	+	0.9577	95.77%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7484	74.84%
P-glycoprotein inhibitior	-	0.7636	76.36%
P-glycoprotein substrate	-	0.8455	84.55%
CYP3A4 substrate	+	0.5458	54.58%
CYP2C9 substrate	-	0.8093	80.93%
CYP2D6 substrate	-	0.8164	81.64%
CYP3A4 inhibition	+	0.5749	57.49%
CYP2C9 inhibition	+	0.6375	63.75%
CYP2C19 inhibition	+	0.7375	73.75%
CYP2D6 inhibition	-	0.8297	82.97%
CYP1A2 inhibition	+	0.8768	87.68%
CYP2C8 inhibition	-	0.9164	91.64%
CYP inhibitory promiscuity	+	0.8535	85.35%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.4169	41.69%
Eye corrosion	-	0.9678	96.78%
Eye irritation	+	0.8215	82.15%
Skin irritation	-	0.6667	66.67%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	+	0.5053	50.53%
Human Ether-a-go-go-Related Gene inhibition	-	0.7711	77.11%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	+	0.6801	68.01%
skin sensitisation	-	0.6218	62.18%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5350	53.50%
Acute Oral Toxicity (c)	II	0.4727	47.27%
Estrogen receptor binding	+	0.6799	67.99%
Androgen receptor binding	+	0.6701	67.01%
Thyroid receptor binding	-	0.5948	59.48%
Glucocorticoid receptor binding	+	0.5719	57.19%
Aromatase binding	-	0.4867	48.67%
PPAR gamma	+	0.5595	55.95%
Honey bee toxicity	-	0.7453	74.53%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9899	98.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.78%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.84%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	92.86%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.69%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.40%	94.00%
CHEMBL2581	P07339	Cathepsin D	89.29%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	86.16%	93.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.19%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.53%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.13%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.70%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.24%	93.65%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.90%	96.09%

Plants that contains it

• Radermachera sinica

Cross-Links

• PubChem: 162915362
• LOTUS: LTS0068416
• wikiData: Q104917698