Qianhucoumarin C

Details

• Internal ID: 0e890f26-22b5-4842-9ddb-4511384db10c
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: [(9R,10S)-9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H](C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)O
• InChI: InChI=1S/C16H16O6/c1-8(17)20-14-12-10(22-16(2,3)15(14)19)6-4-9-5-7-11(18)21-13(9)12/h4-7,14-15,19H,1-3H3/t14-,15+/m0/s1
• InChI Key: IPUBQCBQSUVXEV-LSDHHAIUSA-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

• 118492-23-2
• [(9R,10S)-9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] acetate
• DTXSID20152136

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9506	95.06%
Caco-2	-	0.5450	54.50%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7338	73.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9410	94.10%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5706	57.06%
P-glycoprotein inhibitior	-	0.6968	69.68%
P-glycoprotein substrate	-	0.8530	85.30%
CYP3A4 substrate	+	0.5346	53.46%
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	-	0.7063	70.63%
CYP inhibitory promiscuity	-	0.8987	89.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5005	50.05%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8884	88.84%
Skin irritation	-	0.7732	77.32%
Skin corrosion	-	0.9601	96.01%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5413	54.13%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8816	88.16%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.6685	66.85%
Acute Oral Toxicity (c)	III	0.6858	68.58%
Estrogen receptor binding	+	0.5562	55.62%
Androgen receptor binding	+	0.6390	63.90%
Thyroid receptor binding	-	0.6301	63.01%
Glucocorticoid receptor binding	+	0.6472	64.72%
Aromatase binding	-	0.6058	60.58%
PPAR gamma	+	0.6793	67.93%
Honey bee toxicity	-	0.7962	79.62%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	97.28%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.80%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.80%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.05%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.22%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.16%	94.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.68%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.10%	95.56%

Plants that contains it

• Kitagawia praeruptora

Cross-Links

• PubChem: 196741
• LOTUS: LTS0195301
• wikiData: Q83018737