Epicoccolide B

Details

• Internal ID: 13072ff9-b2e9-4e91-a46b-c9e3fba4ee43
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-(2-formyl-3,4,5-trihydroxy-6-methylphenyl)-6,7-dihydroxy-5-methyl-1-benzofuran-4-carbaldehyde
• SMILES (Canonical): CC1=C(C2=C(C(=C1O)O)OC(=C2)C3=C(C(=C(C(=C3C=O)O)O)O)C)C=O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1O)O)OC(=C2)C3=C(C(=C(C(=C3C=O)O)O)O)C)C=O
• InChI: InChI=1S/C18H14O8/c1-6-9(4-19)8-3-11(26-18(8)17(25)13(6)21)12-7(2)14(22)16(24)15(23)10(12)5-20/h3-5,21-25H,1-2H3
• InChI Key: HTCVSLIHSFBUEL-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄O₈
• Molecular Weight: 358.30 g/mol
• Exact Mass: 358.06886740 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• CHEMBL3104855
• Epicoccolide B_130095
• SCHEMBL14563907
• BDBM50445474
• 2-(2-formyl-3,4,5-trihydroxy-6-methyl-phenyl)-6,7-dihydroxy-5-methyl-benzofuran-4-carbaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9520	95.20%
Caco-2	-	0.5194	51.94%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7362	73.62%
OATP2B1 inhibitior	+	0.5882	58.82%
OATP1B1 inhibitior	-	0.3638	36.38%
OATP1B3 inhibitior	+	0.9047	90.47%
MATE1 inhibitior	-	0.5800	58.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6280	62.80%
P-glycoprotein inhibitior	-	0.8657	86.57%
P-glycoprotein substrate	-	0.8194	81.94%
CYP3A4 substrate	-	0.5089	50.89%
CYP2C9 substrate	-	0.6433	64.33%
CYP2D6 substrate	-	0.8552	85.52%
CYP3A4 inhibition	-	0.6876	68.76%
CYP2C9 inhibition	+	0.6310	63.10%
CYP2C19 inhibition	-	0.7938	79.38%
CYP2D6 inhibition	-	0.9047	90.47%
CYP1A2 inhibition	+	0.8712	87.12%
CYP2C8 inhibition	-	0.6391	63.91%
CYP inhibitory promiscuity	+	0.6124	61.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5285	52.85%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.5846	58.46%
Skin irritation	-	0.6410	64.10%
Skin corrosion	-	0.8817	88.17%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4246	42.46%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8065	80.65%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6673	66.73%
Acute Oral Toxicity (c)	III	0.6072	60.72%
Estrogen receptor binding	+	0.8738	87.38%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	-	0.5800	58.00%
Glucocorticoid receptor binding	+	0.7408	74.08%
Aromatase binding	+	0.5617	56.17%
PPAR gamma	+	0.7433	74.33%
Honey bee toxicity	-	0.8661	86.61%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9818	98.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	250 nM; 250 nM	IC50; IC50	via Super-PRED; PMID: 24328302
CHEMBL2695	Q05397	Focal adhesion kinase 1	800 nM; 800 nM	IC50; IC50	via Super-PRED; PMID: 24328302
CHEMBL3717	P08581	Hepatocyte growth factor receptor	1120 nM	IC50	PMID: 24328302
CHEMBL325	Q13547	Histone deacetylase 1	8800 nM	IC50	PMID: 24328302
CHEMBL5103	Q969S8	Histone deacetylase 10	8100 nM	IC50	PMID: 24328302
CHEMBL1937	Q92769	Histone deacetylase 2	9100 nM	IC50	PMID: 24328302
CHEMBL1829	O15379	Histone deacetylase 3	6900 nM	IC50	PMID: 24328302
CHEMBL1865	Q9UBN7	Histone deacetylase 6	6500 nM	IC50	PMID: 24328302
CHEMBL3192	Q9BY41	Histone deacetylase 8	2100 nM	IC50	PMID: 24328302
CHEMBL1957	P08069	Insulin-like growth factor I receptor	150 nM; 150 nM	IC50; IC50	PMID: 24328302; via Super-PRED
CHEMBL5784	O60285	NUAK family SNF1-like kinase 1	3770 nM	IC50	PMID: 24328302
CHEMBL3384	Q16512	Protein kinase N1	9000 nM	IC50	PMID: 24328302
CHEMBL4282	P31749	Serine/threonine-protein kinase AKT	4070 nM	IC50	PMID: 24328302
CHEMBL2185	Q96GD4	Serine/threonine-protein kinase Aurora-B	7290 nM	IC50	PMID: 24328302
CHEMBL3835	P51955	Serine/threonine-protein kinase NEK2	3780 nM	IC50	PMID: 24328302
CHEMBL4309	Q9HC98	Serine/threonine-protein kinase NEK6	1850 nM	IC50	PMID: 24328302
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	4440 nM	IC50	PMID: 24328302
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	6310 nM	IC50	PMID: 24328302
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	220 nM; 220 nM	IC50; IC50	PMID: 24328302; via Super-PRED
CHEMBL267	P12931	Tyrosine-protein kinase SRC	490 nM; 490 nM	IC50; IC50	via Super-PRED; PMID: 24328302
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	390 nM; 390 nM	IC50; IC50	via Super-PRED; PMID: 24328302

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	98.32%	98.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.38%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.27%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.21%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.02%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.44%	94.73%
CHEMBL2581	P07339	Cathepsin D	90.53%	98.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.91%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.10%	94.00%

Plants that contains it

• Aconitum liangshanicum
• Aconitum sachalinense
• Ageratina gracilis
• Alstonia deplanchei
• Asteriscus graveolens
• Baccharis megapotamica
• Centrosema pascuorum
• Ceratozamia fuscoviridis
• Citrus glauca
• Critonia quadrangularis
• Ficus simplicissima
• Flemingia macrophylla
• Gynura bicolor
• Haplophyllum dauricum
• Marrubium supinum
• Metalasia capitata
• Orthosphenia mexicana
• Oxyanthus speciosus
• Quercus dentata
• Rheum tanguticum
• Rhynchopsidium pumilum
• Senecio latifolius
• Senecio peripotamus
• Solanum elaeagnifolium
• Stevia mercedensis
• Strychnos tabascana
• Styrax hookeri
• Swinglea glutinosa
• Theobroma cacao
• Thuja standishii
• Verbesina rupestris

Cross-Links

• PubChem: 11210533
• NPASS: NPC277510
• ChEMBL: CHEMBL3104855
• LOTUS: LTS0252556
• wikiData: Q77281364