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Antheindurolide A
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C(=C/CC1COC(=O)C1=C)/C[C@@H]1OC(=O)C(=C)C1 |
|---|---|
| InChI | InChI=1S/C15H18O4/c1-9(6-13-7-10(2)14(16)19-13)4-5-12-8-18-15(17)11(12)3/h4,12-13H,2-3,5-8H2,1H3/b9-4-/t12?,13-/m0/s1 |
| InChIKey | KHEYJBCVWLIDAG-HNINGHOPSA-N |
| Formula | C15H18O4 |
| HBA | 4 |
| HBD | 0 |
| MW | 262.3 |
| Rotatable Bonds | 4 |
| TPSA | 52.6 |
| LogP | 2.31 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.47 |
| Exact Mass | 262.12 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Anthemis pseudocotula | Asteraceae | Plantae | 158231 |
Showing of synonyms
Antheindurolide A
- El-Ela MA, Jakupovic J, et al. (1990). Seco-germacranolides from Anthemis pseudocotula.. Phytochemistry,1990, 29(8),2704-2706. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C1)CC=CCC2COC(=O)C2=C
Level: 1
Mol. Weight: 262.3 g/mol
SMILES: C=C1C(=O)OCC1
Level: 0
Mol. Weight: 262.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.05
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.88
- Plasma Protein Binding
- 43.89
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.23
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.25
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.04
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.48
- 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
- 1.34
- Rat (Acute)
- 2.67
- Rat (Chronic Oral)
- 1.7
- Fathead Minnow
- 4.48
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 346.13
- Hydration Free Energy
- -4.58
- Log(D) at pH=7.4
- 1.85
- Log(P)
- 1.84
- Log S
- -3.61
- Log(Vapor Pressure)
- -6.13
- Melting Point
- 60.16
- pKa Acid
- 7.73
- pKa Basic
- 6.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9671 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9671 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8506 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8506 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.8166 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.8166 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8115 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8115 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7593 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7593 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7479 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7479 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7463 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 2 | 0.7463 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7414 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7414 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7402 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7402 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7396 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 2 | 0.7396 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7388 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7388 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7382 |
| Carnitine O-acetyltransferase | P47934 | CACP_MOUSE | Mus musculus | 2 | 0.7382 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7303 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7303 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7299 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7299 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7298 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 2 | 0.7298 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7161 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7161 |
| Pyrrolysine--tRNA ligase | Q8PWY1 | PYLS_METMA | Methanosarcina mazei | 2 | 0.7125 |
| Pyrrolysine--tRNA ligase | Q8PWY1 | PYLS_METMA | Methanosarcina mazei | 2 | 0.7125 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7102 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 2 | 0.7102 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7099 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7099 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7094 |
| Quorum-sensing transcriptional activator | Q8XBD0 | Q8XBD0_ECO57 | Escherichia coli O157:H7 | 2 | 0.7094 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 2 | 0.7077 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 2 | 0.7077 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7034 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7034 |