Isobutyrolactone II - Compound Card

Isobutyrolactone II

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Isobutyrolactone II

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Butyrolactone Derivative
Canonical Smiles CO[C@]1(Cc2ccc(cc2)O)OC(=O)C(=C1c1ccc(cc1)O)O
InChI InChI=1S/C18H16O6/c1-23-18(10-11-2-6-13(19)7-3-11)15(16(21)17(22)24-18)12-4-8-14(20)9-5-12/h2-9,19-21H,10H2,1H3/t18-/m1/s1
InChIKey NIRMZWVJIJSJIF-GOSISDBHSA-N
Formula C18H16O6
HBA 6
HBD 3
MW 328.32
Rotatable Bonds 4
TPSA 96.22
LogP 2.51
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 328.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • 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]
Pubchem: 122204305
Nmrshiftdb2: 70007032

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 328.32 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 328.32 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 328.32 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 328.32 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 328.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
61.2
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.550
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.640
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
1.230
Rat (Acute)
2.240
Rat (Chronic Oral)
2.620
Fathead Minnow
4.350
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
438.130
Hydration Free Energy
-9.250
Log(D) at pH=7.4
1.940
Log(P)
1.07
Log S
-3.09
Log(Vapor Pressure)
-7.51
Melting Point
211.27
pKa Acid
7.56
pKa Basic
2.57
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 0.9416
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9416
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9197
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9197
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9074
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9074
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9051
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.9051
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9031
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8944
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8944
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8837
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8837
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8835
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8835
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8797
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8797
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8710
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8710
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8545
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8545
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8451
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8451
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8398
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8398
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8351
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8351
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8207
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.8207
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8167
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8167
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8161
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8161
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8128
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8128
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.8104
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.8104
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8001
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8001
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7913
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7913
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7903
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7903
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7819
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.7819
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7743
Acetolactate synthase catalytic subunit, mitochondrial P07342 ILVB_YEAST Saccharomyces cerevisiae 3 0.7743
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7735
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7735
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7667
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7667
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7649
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7649
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7642
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7642
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7575
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7575
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7575
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7575
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7574
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 3 0.7574
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7558
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7558
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7523
GCN5-related N-acetyltransferase Q3M362 Q3M362_TRIV2 Trichormus variabilis 3 0.7523
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7523
GCN5-related N-acetyltransferase Q3M362 Q3M362_TRIV2 Trichormus variabilis 3 0.7523
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7507
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7507
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7507
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7507
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7505
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7505
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7435
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7435
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7424
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7424
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7407
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7407
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7404
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7404
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7371
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7371
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7360
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7360
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7359
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7359
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7321
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7301
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7301
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7301
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7301
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7287
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7287
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7258
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7258
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7258
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7258
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7252
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7252
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7220
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7220
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7214
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7214
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 3 0.7209
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 3 0.7209
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7200
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7200
Ribosomal RNA large subunit methyltransferase H P0C1V0 RLMH_STAAU Staphylococcus aureus 3 0.7198
Ribosomal RNA large subunit methyltransferase H P0C1V0 RLMH_STAAU Staphylococcus aureus 3 0.7198
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7197
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7197
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7185
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7185
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7183
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7183
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7183
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7183
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7183
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7183
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7167
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7167
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7165
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7165
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7164
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7164
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7162
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7162
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7143
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7143
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7123
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7123
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7118
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7118
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7115
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7115
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7103
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7103
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 2 0.7100
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 2 0.7100
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7084
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7084
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7079
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7079
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7047
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7047
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7025
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7025
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7025
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7025
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7024
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7024
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7024
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7024
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7010
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7010
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7005
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7005

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