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Butyrolactone III
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Lactone
- Subclass: Butyrolactone Derivative
| Canonical Smiles | COC(=O)C1(Cc2ccc(c(c2)CC2OC2(C)C)O)OC(=O)C(=C1c1ccc(cc1)O)O |
|---|---|
| InChI | InChI=1S/C24H24O8/c1-23(2)18(31-23)11-15-10-13(4-9-17(15)26)12-24(22(29)30-3)19(20(27)21(28)32-24)14-5-7-16(25)8-6-14/h4-10,18,25-27H,11-12H2,1-3H3 |
| InChIKey | FWHAYHIGJSFGKO-UHFFFAOYSA-N |
| Formula | C24H24O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 440.45 |
| Rotatable Bonds | 6 |
| TPSA | 125.82 |
| LogP | 2.8 |
| 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 terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Butyrolactone III
MLS000877035
MEGxm0_000070
CHEMBL1461124
ACon0_000894
ACon1_002214
HMS2270H16
NCGC00179715-01
SMR000440635
Methyl 2-[[3-[(3,3-dimethyloxiran-2-yl)methyl]-4-hydroxyphenyl]methyl]-4-hydroxy-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate
- Chen H, Daletos G, et al. (2015). Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture. Phytochemistry Letters,2015,12,35-41. [View]
No compound-protein relationship available.
SMILES: O1CC1Cc2cc(ccc2)CC3OC(=O)C=C3c4ccccc4
Level: 3
Mol. Weight: 440.45 g/mol
SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3
Level: 2
Mol. Weight: 440.45 g/mol
SMILES: O1CC1Cc2cc(ccc2)CC(O3)C=CC3=O
Level: 2
Mol. Weight: 440.45 g/mol
SMILES: O=C1C=CC(O1)Cc2ccccc2
Level: 1
Mol. Weight: 440.45 g/mol
SMILES: C1OC(=O)C=C1c2ccccc2
Level: 1
Mol. Weight: 440.45 g/mol
SMILES: O1CC1Cc2ccccc2
Level: 1
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
SMILES: C1CO1
Level: 0
Mol. Weight: 440.45 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -5.26
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.860
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.75
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.850
- Plasma Protein Binding
- 0.16
- 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
- Non-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
- 12.160
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.260
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.250
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.350
- 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
- -75.750
- Rat (Acute)
- 2.470
- Rat (Chronic Oral)
- 2.660
- Fathead Minnow
- 5.090
- 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
- 491.340
- Hydration Free Energy
- -2.950
- Log(D) at pH=7.4
- 2.120
- Log(P)
- 1.77
- Log S
- -3.48
- Log(Vapor Pressure)
- -8.22
- Melting Point
- 170.49
- pKa Acid
- 7.31
- pKa Basic
- 2.59
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9296 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9296 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.9054 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.9054 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.8985 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.8985 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8820 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8820 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8695 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8695 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8685 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8685 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8510 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8510 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8462 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8462 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8409 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8409 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8365 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8365 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8306 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 3 | 0.8306 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8258 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 3 | 0.8258 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.8210 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.8210 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8084 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8084 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8083 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8083 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8059 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8059 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8004 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8004 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7949 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7949 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7894 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7894 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7871 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7871 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7813 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7813 |
| GCN5-related N-acetyltransferase | Q3M362 | Q3M362_TRIV2 | Trichormus variabilis | 3 | 0.7812 |
| GCN5-related N-acetyltransferase | Q3M362 | Q3M362_TRIV2 | Trichormus variabilis | 3 | 0.7812 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7766 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7766 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7717 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7717 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7686 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7686 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 3 | 0.7666 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 3 | 0.7666 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7650 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7650 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7637 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7637 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7561 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7561 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7546 |
| Methylmalonyl-CoA decarboxylase | P52045 | SCPB_ECOLI | Escherichia coli | 3 | 0.7546 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7503 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7503 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7461 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7461 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7459 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7459 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7445 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7445 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7441 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7441 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7437 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7437 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7411 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7411 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7402 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7402 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7400 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7400 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7399 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7399 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7344 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7344 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7321 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7321 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7303 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7303 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7283 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7283 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7264 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7264 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7259 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7259 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7239 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7239 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7202 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7202 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7189 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7189 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7187 |
| Adenosine monophosphate-protein transferase | Q8ZVF7 | Q8ZVF7_PYRAE | Pyrobaculum aerophilum | 3 | 0.7187 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7150 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 2 | 0.7150 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7140 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7140 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7130 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7130 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7041 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7041 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7039 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7039 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.7033 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.7033 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7004 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7004 |