Epicocconigrone B - Compound Card

Epicocconigrone B

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Epicocconigrone B

Structure
Zoomed Structure
  • Family: Fungi - Incertae sedis
  • Kingdom: Fungi
  • Class: Polyketide
Canonical Smiles Cc1c(O)c(O)c(c2c1C(=O)[C@]1([C@@](C2)(C)C(=C(C1=O)C)C)O)O
InChI InChI=1S/C17H18O6/c1-6-8(3)16(4)5-9-10(15(22)17(16,23)14(6)21)7(2)11(18)13(20)12(9)19/h18-20,23H,5H2,1-4H3/t16-,17-/m1/s1
InChIKey YKRJBZOAJFAGBE-IAGOWNOFSA-N
Formula C17H18O6
HBA 6
HBD 4
MW 318.32
Rotatable Bonds 0
TPSA 115.06
LogP 1.51
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 318.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Epicoccum nigrum Incertae sedis Fungi 105696

Showing of synonyms

  • 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: 163037185
Nmrshiftdb2: 80003386

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 318.32 g/mol

Cell proliferation inhibition
Hdac inhibition
Protein kinase inhibition

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
80.64
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
13.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.55
Micronucleos
Toxic
NR-AhR
Toxic
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
2.22
Rat (Acute)
2.37
Rat (Chronic Oral)
3.03
Fathead Minnow
4.04
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
425.51
Hydration Free Energy
-9.16
Log(D) at pH=7.4
1.03
Log(P)
1.6
Log S
-2.42
Log(Vapor Pressure)
-8.34
Melting Point
232.27
pKa Acid
4.03
pKa Basic
6.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8793
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8793
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7923
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7923
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7587
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7587
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 5 0.7497
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 5 0.7497
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7184
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7184
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7162
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7162
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7155
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7155
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7100
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7032
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7032
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7000
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7000

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