(8R)-8-[(3S)-3-hydroperoxy-4-methylpent-4-enyl]-8-methylpyrano[2,3-f]chromen-2-one

Details

• Internal ID: dd64f032-4bf7-424a-96ca-5036e32ebc39
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: (8R)-8-[(3S)-3-hydroperoxy-4-methylpent-4-enyl]-8-methylpyrano[2,3-f]chromen-2-one
• SMILES (Canonical): CC(=C)C(CCC1(C=CC2=C(O1)C=CC3=C2OC(=O)C=C3)C)OO
• SMILES (Isomeric): CC(=C)[C@H](CC[C@@]1(C=CC2=C(O1)C=CC3=C2OC(=O)C=C3)C)OO
• InChI: InChI=1S/C19H20O5/c1-12(2)15(24-21)9-11-19(3)10-8-14-16(23-19)6-4-13-5-7-17(20)22-18(13)14/h4-8,10,15,21H,1,9,11H2,2-3H3/t15-,19-/m0/s1
• InChI Key: QGZAVSKJRVEPBX-KXBFYZLASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.13107373 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.17
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9619	96.19%
Caco-2	-	0.5686	56.86%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7158	71.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.8396	83.96%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7946	79.46%
P-glycoprotein inhibitior	-	0.6244	62.44%
P-glycoprotein substrate	-	0.6539	65.39%
CYP3A4 substrate	+	0.5795	57.95%
CYP2C9 substrate	-	0.6381	63.81%
CYP2D6 substrate	-	0.8137	81.37%
CYP3A4 inhibition	-	0.6710	67.10%
CYP2C9 inhibition	-	0.5693	56.93%
CYP2C19 inhibition	-	0.5568	55.68%
CYP2D6 inhibition	-	0.8532	85.32%
CYP1A2 inhibition	+	0.5086	50.86%
CYP2C8 inhibition	-	0.5822	58.22%
CYP inhibitory promiscuity	-	0.5186	51.86%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6132	61.32%
Eye corrosion	-	0.9835	98.35%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.7115	71.15%
Skin corrosion	-	0.9059	90.59%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8612	86.12%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5605	56.05%
skin sensitisation	-	0.7709	77.09%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5420	54.20%
Acute Oral Toxicity (c)	III	0.4668	46.68%
Estrogen receptor binding	+	0.8354	83.54%
Androgen receptor binding	+	0.7072	70.72%
Thyroid receptor binding	+	0.6493	64.93%
Glucocorticoid receptor binding	+	0.8385	83.85%
Aromatase binding	+	0.7668	76.68%
PPAR gamma	+	0.7937	79.37%
Honey bee toxicity	-	0.7723	77.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5450	54.50%
Fish aquatic toxicity	+	0.9944	99.44%

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	96.50%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.49%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	86.95%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	85.38%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.92%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.95%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.16%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.14%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.12%	95.56%

Plants that contains it

• Boronia lanceolata

Cross-Links

• PubChem: 162985002
• LOTUS: LTS0045705
• wikiData: Q105220781