Epicoccolide A - Compound Card

Epicoccolide A

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Epicoccolide A

Structure
Zoomed Structure
  • Family: Fungi - Didymellaceae
  • Kingdom: Fungi
  • Class: Phenolic
Canonical Smiles O=Cc1c2[C@H]3O[C@@H](Oc2c(c(c1C)O)O)c1c(C3=O)c(C)c(c(c1O)O)O
InChI InChI=1S/C18H14O9/c1-4-6(3-19)8-16-13(23)7-5(2)11(21)14(24)12(22)9(7)18(26-16)27-17(8)15(25)10(4)20/h3,16,18,20-22,24-25H,1-2H3/t16-,18+/m1/s1
InChIKey VFBCGYVZJVAFIO-AEFFLSMTSA-N
Formula C18H14O9
HBA 9
HBD 5
MW 374.3
Rotatable Bonds 1
TPSA 153.75
LogP 1.99
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 374.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 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]
Pubchem: 71732639
Nmrshiftdb2: 80020113

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C3Oc4c(C(O3)C2=O)cccc4

Level: 0

Mol. Weight: 374.3 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-6.38
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.31
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.71

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
79.68
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.91
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.58
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.38
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.52
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
-2.06
Rat (Acute)
2.52
Rat (Chronic Oral)
3.22
Fathead Minnow
4.28
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
527.56
Hydration Free Energy
-9.75
Log(D) at pH=7.4
0.66
Log(P)
1.72
Log S
-3.92
Log(Vapor Pressure)
-8.91
Melting Point
250.78
pKa Acid
5.85
pKa Basic
4.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 5 0.7388
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7292
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7254
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7196
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7119

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