[(9S,10S)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: c63abbc1-16e2-4900-adc2-29d41d32ae4c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [(9S,10S)-9-acetyloxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC1C(O1)(C)C(=O)OC2C(C(OC3=C2C4=C(C=C3)C=CC(=O)O4)(C)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1[C@](O1)(C)C(=O)O[C@@H]2[C@@H](C(OC3=C2C4=C(C=C3)C=CC(=O)O4)(C)C)OC(=O)C
• InChI: InChI=1S/C21H22O8/c1-10-21(5,28-10)19(24)27-17-15-13(29-20(3,4)18(17)25-11(2)22)8-6-12-7-9-14(23)26-16(12)15/h6-10,17-18H,1-5H3/t10-,17+,18+,21-/m1/s1
• InChI Key: LNVSQOCOMICZRK-QIBLFXCUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	+	0.6896	68.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6348	63.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9361	93.61%
OATP1B3 inhibitior	+	0.9741	97.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6238	62.38%
P-glycoprotein inhibitior	+	0.7978	79.78%
P-glycoprotein substrate	-	0.7601	76.01%
CYP3A4 substrate	+	0.5947	59.47%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.6787	67.87%
CYP2C9 inhibition	-	0.8726	87.26%
CYP2C19 inhibition	-	0.7304	73.04%
CYP2D6 inhibition	-	0.9347	93.47%
CYP1A2 inhibition	-	0.5813	58.13%
CYP2C8 inhibition	-	0.5744	57.44%
CYP inhibitory promiscuity	-	0.7617	76.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4982	49.82%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.7791	77.91%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7786	77.86%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5839	58.39%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.8100	81.00%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.6448	64.48%
Glucocorticoid receptor binding	+	0.6866	68.66%
Aromatase binding	-	0.4872	48.72%
PPAR gamma	+	0.6893	68.93%
Honey bee toxicity	-	0.7826	78.26%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9828	98.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.54%	83.82%
CHEMBL2581	P07339	Cathepsin D	97.14%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.71%	91.11%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	91.56%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.52%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.03%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.73%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.68%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.58%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.08%	86.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.70%	85.11%

Plants that contains it

• Krubera peregrina

Cross-Links

• PubChem: 162958614
• LOTUS: LTS0019900
• wikiData: Q105154522