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Butyrolactone IV
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Lignan
| Canonical Smiles | COC(=O)[C@]1(Cc2ccc3c(c2)C[C@@H](O3)C(O)(C)C)OC(=O)C(=C1c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C24H24O8/c1-23(2,29)18-11-15-10-13(4-9-17(15)31-18)12-24(22(28)30-3)19(20(26)21(27)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-26,29H,11-12H2,1-3H3/t18-,24-/m1/s1 |
| InChIKey | NVAIFFOQCAKMAH-HOYKHHGWSA-N |
| Formula | C24H24O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 440.45 |
| Rotatable Bonds | 5 |
| TPSA | 122.52 |
| LogP | 2.45 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.33 |
| Exact Mass | 440.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus versicolor | Trichocomaceae | Fungi | 46472 |
Showing of synonyms
Butyrolactone IV
Butylrolactone IV
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-(((2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl)methyl)-5-oxo-2,5-dihydrofuran-2-carboxylic acid
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-(((2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl)methyl)-5-oxofuran-2-carboxylate
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl]-5-oxofuran-2-carboxylate
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-{[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]methyl}-5-oxo-2,5-dihydrofuran-2-carboxylic acid
CHEMBL2035562
CHEBI:201657
BDBM50453564
CCG-208783
Methyl (2R)-4-hydroxy-3-(4-hydroxyphenyl)-2-[[(2R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzouran-5-yl]methyl]-5-oxouran-2-carboxylate
- Mohamed G, Ibrahim S, et al. (2020). Antimicrobial metabolites from the endophytic fungus Aspergillus versicolor. Phytochemistry Letters,2020,35,152–155. [View]
Pubchem:
11743953
Zinc:
ZINC000035466088
Nmrshiftdb2:
70046692
Chembl:
CHEMBL2035562
Bindingdb:
50453564
No compound-protein relationship available.
SMILES: C1COc(c12)ccc(c2)CC3OC(=O)C=C3c4ccccc4
Level: 2
Mol. Weight: 440.45 g/mol
SMILES: O=C1C=CC(O1)Cc(c2)ccc(c23)OCC3
Level: 1
Mol. Weight: 440.45 g/mol
SMILES: C1OC(=O)C=C1c2ccccc2
Level: 1
Mol. Weight: 440.45 g/mol
SMILES: C1COc(c12)cccc2
Level: 0
Mol. Weight: 440.45 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 440.45 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 440.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.31
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.860
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.54
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.950
- Plasma Protein Binding
- 75.89
- 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
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.170
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.180
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.360
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.050
- 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
- -76.530
- Rat (Acute)
- 2.300
- Rat (Chronic Oral)
- 2.530
- Fathead Minnow
- 4.860
- 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
- 486.200
- Hydration Free Energy
- -2.810
- Log(D) at pH=7.4
- 2.410
- Log(P)
- 1.87
- Log S
- -3.69
- Log(Vapor Pressure)
- -9.54
- Melting Point
- 231.73
- pKa Acid
- 7.54
- pKa Basic
- 4.16
| 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 | 0.9394 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.9338 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8991 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8939 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8855 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8811 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8749 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8730 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8527 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8447 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.8439 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8222 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8171 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8064 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8015 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.7937 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7850 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.7830 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7825 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7797 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.7755 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.7744 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7737 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7721 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7651 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7605 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7583 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7558 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7554 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7500 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7427 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7422 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7408 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7400 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7393 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7389 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 4 | 0.7347 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7336 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7321 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7317 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7297 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7291 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7256 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7254 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7250 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7246 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7204 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7190 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.7123 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7085 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7066 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7063 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 3 | 0.7061 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7036 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7011 |