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Aspernolide F
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Terpenoid
| Canonical Smiles | CCOC1=C(c2ccc(cc2)O)[C@](OC1=O)(Cc1ccc(c(c1)CC=C(C)C)O)C(=O)OC |
|---|---|
| InChI | InChI=1S/C26H28O7/c1-5-32-23-22(18-9-11-20(27)12-10-18)26(25(30)31-4,33-24(23)29)15-17-7-13-21(28)19(14-17)8-6-16(2)3/h6-7,9-14,27-28H,5,8,15H2,1-4H3/t26-/m1/s1 |
| InChIKey | DQKWENVYPMUZIN-AREMUKBSSA-N |
| Formula | C26H28O7 |
| HBA | 7 |
| HBD | 2 |
| MW | 452.5 |
| Rotatable Bonds | 8 |
| TPSA | 102.29 |
| LogP | 4.07 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.31 |
| Exact Mass | 452.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Aspernolide F
Methyl (2R)-4-ethoxy-2-((4-hydroxy-3-(3-methylbut-2-enyl)phenyl)methyl)-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate
Methyl (2R)-4-ethoxy-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate
CHEBI:217160
Methyl (2R)-4-ethoxy-2-[[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]methyl]-3-(4-hydroxyphenyl)-5-oxouran-2-carboxylate
- Ibrahim S, Elkhayat E, et al. (2015). Aspernolides F and G, new butyrolactones from the endophytic fungus Aspergillus terreus. Phytochemistry Letters, 2015,14,84–90. [View]
No compound-protein relationship available.
SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3
Level: 2
Mol. Weight: 452.5 g/mol
SMILES: O=C1C=CC(O1)Cc2ccccc2
Level: 1
Mol. Weight: 452.5 g/mol
SMILES: C1OC(=O)C=C1c2ccccc2
Level: 1
Mol. Weight: 452.5 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 452.5 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 452.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.78
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.81
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.07
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.03
- Plasma Protein Binding
- 58.64
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.41
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.63
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.55
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.27
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -100.63
- Rat (Acute)
- 1.96
- Rat (Chronic Oral)
- 2.34
- Fathead Minnow
- 5.46
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 474.84
- Hydration Free Energy
- -2.7
- Log(D) at pH=7.4
- 3.45
- Log(P)
- 3.96
- Log S
- -4.63
- Log(Vapor Pressure)
- -8.69
- Melting Point
- 164.69
- pKa Acid
- 8.35
- pKa Basic
- 5.53
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9525 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.9314 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8715 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8632 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8446 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8429 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8377 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8344 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8342 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8051 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7848 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7819 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7794 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7666 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7664 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7622 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.7575 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7493 |
| Metallo-beta-lactamase type 2 | P52699 | BLAB_SERMA | Serratia marcescens | 3 | 0.7455 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7443 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7404 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7311 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7271 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7262 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7260 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.7251 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7239 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7213 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7122 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7117 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7085 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7052 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7035 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7015 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7009 |