Epicoccamide - Compound Card

Epicoccamide

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Epicoccamide

Structure
Zoomed Structure
  • Family: Fungi - Didymellaceae
  • Kingdom: Fungi
  • Class: Alkaloid
Canonical Smiles OC[C@H]1O[C@@H](OCCCCCCCCCCCCCCC(/C(=C/2\C(=O)N(C(C2=O)C)C)/O)C)[C@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C29H51NO9/c1-19(23(32)22-24(33)20(2)30(3)28(22)37)16-14-12-10-8-6-4-5-7-9-11-13-15-17-38-29-27(36)26(35)25(34)21(18-31)39-29/h19-21,25-27,29,31-32,34-36H,4-18H2,1-3H3/b23-22+/t19?,20?,21-,25-,26+,27+,29-/m1/s1
InChIKey GLMMQSHEMIVRFP-TYNIBPNFSA-N
Formula C29H51NO9
HBA 9
HBD 5
MW 557.73
Rotatable Bonds 18
TPSA 156.99
LogP 2.75
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 557.36
Number of Lipinski Rule Violations 1
# 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: 54716910
Nmrshiftdb2: 70050096

No compound-protein relationship available.

Structure

SMILES: O=C1NCC(=O)C1=CCCCCCCCCCCCCCCCOC2CCCCO2

Level: 1

Mol. Weight: 557.73 g/mol

Structure

SMILES: C=C1C(=O)CNC1=O

Level: 0

Mol. Weight: 557.73 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 557.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.000
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.180
Plasma Protein Binding
91.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-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
0.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.960
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.500
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.010
Micronucleos
Safe
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
-1412.040
Rat (Acute)
2.530
Rat (Chronic Oral)
3.540
Fathead Minnow
4.800
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
520.310
Hydration Free Energy
-2.830
Log(D) at pH=7.4
2.970
Log(P)
3.51
Log S
-3.53
Log(Vapor Pressure)
-13.6
Melting Point
114.36
pKa Acid
5.32
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.9319
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9072
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8632
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8289
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8158
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7988
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7909
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7905
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7904
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7819
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7722
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7645
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7636
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7496
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7471
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7448
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7436
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7352
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7351
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7307
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7207
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7175
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7174
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7162
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7144
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7144
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7110
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7079
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7075
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7066
diphosphomevalonate decarboxylase Q9FD73 Q9FD73_STAEP Staphylococcus epidermidis 2 0.7057
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7004
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7001

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