Phyllocoumarin

Details

• Internal ID: 7e5d3e82-99ef-42af-b8a5-4e8975755b03
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-pyrano[2,3-f]chromen-8-one
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C=CC(=O)O3)O)C4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2C=CC(=O)O3)O)C4=CC(=C(C=C4)O)O)O
• InChI: InChI=1S/C18H14O7/c19-11-3-1-8(5-13(11)21)17-14(22)6-10-12(20)7-15-9(18(10)25-17)2-4-16(23)24-15/h1-5,7,14,17,19-22H,6H2/t14-,17+/m0/s1
• InChI Key: JXVQELAURPRTFD-WMLDXEAASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₇
• Molecular Weight: 342.30 g/mol
• Exact Mass: 342.07395278 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.95
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• CHEBI:167944
• LMPK12020070
• (2R,3S)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-pyrano[2,3-]chromen-8-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9353	93.53%
Caco-2	-	0.8279	82.79%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7416	74.16%
OATP2B1 inhibitior	+	0.5584	55.84%
OATP1B1 inhibitior	+	0.9418	94.18%
OATP1B3 inhibitior	+	0.8491	84.91%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7792	77.92%
P-glycoprotein inhibitior	-	0.7824	78.24%
P-glycoprotein substrate	-	0.8051	80.51%
CYP3A4 substrate	+	0.5335	53.35%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.7706	77.06%
CYP3A4 inhibition	-	0.9404	94.04%
CYP2C9 inhibition	-	0.8302	83.02%
CYP2C19 inhibition	-	0.9153	91.53%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.9311	93.11%
CYP2C8 inhibition	-	0.6087	60.87%
CYP inhibitory promiscuity	-	0.9703	97.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9916	99.16%
Eye irritation	+	0.7121	71.21%
Skin irritation	-	0.5844	58.44%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6525	65.25%
Micronuclear	+	0.8859	88.59%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8145	81.45%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8201	82.01%
Acute Oral Toxicity (c)	II	0.3483	34.83%
Estrogen receptor binding	+	0.7781	77.81%
Androgen receptor binding	+	0.7920	79.20%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	+	0.8455	84.55%
Aromatase binding	+	0.7082	70.82%
PPAR gamma	+	0.7352	73.52%
Honey bee toxicity	-	0.7813	78.13%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8718	87.18%

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	99.73%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.43%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.64%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.14%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.21%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.34%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.01%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.96%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.23%	99.15%
CHEMBL2535	P11166	Glucose transporter	84.67%	98.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.40%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	80.59%	94.73%

Plants that contains it

• Phyllocladus trichomanoides
• Schisandra lancifolia
• Smilax corbularia

Cross-Links

• PubChem: 44257095
• LOTUS: LTS0025543
• wikiData: Q76546125