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Epicoccolide B

Family: Fungi - Didymellaceae
Kingdom: Fungi
Class: Phenolic

Canonical Smiles	O=Cc1c(c2cc3c(o2)c(O)c(c(c3C=O)C)O)c(C)c(c(c1O)O)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
InChIKey	HTCVSLIHSFBUEL-UHFFFAOYSA-N
Formula	C₁₈H₁₄O₈
HBA	8
HBD	5
MW	358.3
Rotatable Bonds	3
TPSA	148.43
LogP	2.87
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.11
Exact Mass	358.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Epicoccum nigrum	Incertae sedis	Fungi	105696
2	Epicoccum sp.	Didymellaceae	Fungi	1859956

Showing of synonyms

Talontsi FM, Dittrich B, et al. (2013). Epicoccolides: Antimicrobial and Antifungal Polyketides from an Endophytic Fungus Epicoccum sp. Associated with Theobroma cacao. Eur. J. Org. Chem., 2013: 3174-3180. [View]
El Amrani M, Lai D, et al. (2014). Protein kinase and HDAC inhibitors from the endophytic fungus epicoccum nigrum. Journal of Natural Products,2014,77(1),49-56. [View] [PubMed]

Pubchem: 11210533

Gnps: CCMSLIB00000478515

Zinc: ZINC000103236203

Nmrshiftdb2: 70007608

Chembl: CHEMBL3104855

Bindingdb: 50445474

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(c2)-c3ccccc3

Level: 1

Mol. Weight: 358.3 g/mol

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 358.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.3 g/mol

Antimicrobial

Cell proliferation inhibition

Hdac inhibition

Protein kinase inhibition

Absorption

Caco-2 (logPapp): -5.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.42
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.45

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.4
Plasma Protein Binding: 67.25
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.46
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.99
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.89
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.07
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.36
Rat (Acute): 2.42
Rat (Chronic Oral): 3.05
Fathead Minnow: 4.32
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 525.83
Hydration Free Energy: -9.85
Log(D) at pH=7.4: 1.08
Log(P): 3.09
Log S: -3.81
Log(Vapor Pressure): -9.57
Melting Point: 252.67
pKa Acid: 4.97
pKa Basic: 4.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9260
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9260
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8802
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8802
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8449
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8449
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8443
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8443
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8322
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8322
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8304
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8304
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8212
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8212
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8195
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8195
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8143
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8143
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8042
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8042
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8012
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8012
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7938
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7938
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7936
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7936
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7871
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7871
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7794
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7794
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7734
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7734
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7692
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7692
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7646
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.7646
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7640
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7640
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7589
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7589
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7586
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7586
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	4	0.7560
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	4	0.7560
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7553
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7553
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7530
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7530
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7518
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7518
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7504
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7504
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7421
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7421
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7312
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	3	0.7312
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7284
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7284
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7271
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7271
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7219
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7219
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7196
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7196
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7142
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7142
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7124
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7124
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7089
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7089
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7086
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7086
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7076
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7076
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7076
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7076
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7072
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7072
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7058
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7058
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	4	0.7036
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	4	0.7036

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