6-[(1R,2R)-1,2-dihydroxy-3-methylbut-3-enyl]-7,8-dimethoxychromen-2-one

Details

• Internal ID: 6ed70327-cf2e-4bc1-b2b5-bd225d1589a3
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 6-[(1R,2R)-1,2-dihydroxy-3-methylbut-3-enyl]-7,8-dimethoxychromen-2-one
• SMILES (Canonical): CC(=C)C(C(C1=C(C(=C2C(=C1)C=CC(=O)O2)OC)OC)O)O
• SMILES (Isomeric): CC(=C)[C@H]([C@@H](C1=C(C(=C2C(=C1)C=CC(=O)O2)OC)OC)O)O
• InChI: InChI=1S/C16H18O6/c1-8(2)12(18)13(19)10-7-9-5-6-11(17)22-14(9)16(21-4)15(10)20-3/h5-7,12-13,18-19H,1H2,2-4H3/t12-,13-/m1/s1
• InChI Key: OWNYOCZJNPJVQZ-CHWSQXEVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₆
• Molecular Weight: 306.31 g/mol
• Exact Mass: 306.11033829 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9408	94.08%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5894	58.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9435	94.35%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5909	59.09%
P-glycoprotein inhibitior	-	0.6928	69.28%
P-glycoprotein substrate	-	0.9049	90.49%
CYP3A4 substrate	-	0.5861	58.61%
CYP2C9 substrate	-	0.8331	83.31%
CYP2D6 substrate	-	0.8223	82.23%
CYP3A4 inhibition	-	0.6549	65.49%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	+	0.6132	61.32%
CYP2D6 inhibition	-	0.8888	88.88%
CYP1A2 inhibition	+	0.5168	51.68%
CYP2C8 inhibition	-	0.8393	83.93%
CYP inhibitory promiscuity	+	0.5493	54.93%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5653	56.53%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.8570	85.70%
Skin irritation	-	0.7046	70.46%
Skin corrosion	-	0.9623	96.23%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5880	58.80%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8066	80.66%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6216	62.16%
Acute Oral Toxicity (c)	II	0.4895	48.95%
Estrogen receptor binding	+	0.6327	63.27%
Androgen receptor binding	+	0.5357	53.57%
Thyroid receptor binding	+	0.5272	52.72%
Glucocorticoid receptor binding	+	0.6882	68.82%
Aromatase binding	+	0.6630	66.30%
PPAR gamma	+	0.6163	61.63%
Honey bee toxicity	-	0.8930	89.30%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	96.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.41%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.96%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.60%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.19%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.34%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.21%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	85.17%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.27%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.19%	96.95%
CHEMBL2535	P11166	Glucose transporter	81.96%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.79%	99.17%

Plants that contains it

• Fatoua villosa

Cross-Links

• PubChem: 49831604
• LOTUS: LTS0033553
• wikiData: Q105202160