Qianhucoumarin B

Details

• Internal ID: 1521c596-0da4-45c2-8fc8-9a09b0ee56cb
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [(9S,10S)-10-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] acetate
• InChI: InChI=1S/C16H16O6/c1-8(17)20-15-13(19)12-10(22-16(15,2)3)6-4-9-5-7-11(18)21-14(9)12/h4-7,13,15,19H,1-3H3/t13-,15-/m0/s1
• InChI Key: WGBFEDHNTNVZGG-ZFWWWQNUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.29 g/mol
• Exact Mass: 304.09468823 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 152615-14-0
• [(9S,10S)-10-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-9-yl] acetate
• DTXSID00165087
• 2H,8H-Benzo(1,2-b:3,4-b')dipyran-2-one, 9-(acetyloxy)-9,10-dihydro-10-hydroxy-8,8-dimethyl-, (9S-cis)-
• ((9S,10S)-10-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano(2,3-f)chromen-9-yl) acetate
• RefChem:178006
• DTXCID5087578
• orb1943430
• HY-N11791
• CS-0851552
• G89047

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9506	95.06%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7338	73.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9320	93.20%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6563	65.63%
P-glycoprotein inhibitior	-	0.4812	48.12%
P-glycoprotein substrate	-	0.8903	89.03%
CYP3A4 substrate	+	0.5387	53.87%
CYP2C9 substrate	-	0.8175	81.75%
CYP2D6 substrate	-	0.8404	84.04%
CYP3A4 inhibition	-	0.8035	80.35%
CYP2C9 inhibition	-	0.8744	87.44%
CYP2C19 inhibition	-	0.9103	91.03%
CYP2D6 inhibition	-	0.9503	95.03%
CYP1A2 inhibition	-	0.7274	72.74%
CYP2C8 inhibition	-	0.6782	67.82%
CYP inhibitory promiscuity	-	0.8987	89.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5005	50.05%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8625	86.25%
Skin irritation	-	0.7732	77.32%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4729	47.29%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8816	88.16%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6258	62.58%
Acute Oral Toxicity (c)	III	0.6858	68.58%
Estrogen receptor binding	+	0.8066	80.66%
Androgen receptor binding	+	0.6200	62.00%
Thyroid receptor binding	-	0.5772	57.72%
Glucocorticoid receptor binding	+	0.5770	57.70%
Aromatase binding	+	0.5619	56.19%
PPAR gamma	-	0.5928	59.28%
Honey bee toxicity	-	0.8157	81.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9760	97.60%

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	98.41%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.81%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.06%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.28%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.89%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.37%	96.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.83%	81.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.10%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.79%	91.19%

Plants that contains it

• Angelica decursiva
• Kitagawia praeruptora

Cross-Links

• PubChem: 197634
• NPASS: NPC301224
• LOTUS: LTS0139752
• wikiData: Q83034238