4-O-demethylisobutyrolactone II - Compound Card

4-O-demethylisobutyrolactone II

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4-O-demethylisobutyrolactone II

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Butyrolactone Derivative
Canonical Smiles Oc1ccc(cc1)C[C@@]1(O)OC(=O)C(=C1c1ccc(cc1)O)O
InChI InChI=1S/C17H14O6/c18-12-5-1-10(2-6-12)9-17(22)14(15(20)16(21)23-17)11-3-7-13(19)8-4-11/h1-8,18-20,22H,9H2/t17-/m1/s1
InChIKey UJWXDHBTYAGSML-QGZVFWFLSA-N
Formula C17H14O6
HBA 6
HBD 4
MW 314.29
Rotatable Bonds 3
TPSA 107.22
LogP 1.85
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 314.08
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: 122204306
Nmrshiftdb2: 70007033

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 314.29 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 314.29 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 314.29 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 314.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.930
Plasma Protein Binding
69.96
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.070
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.570
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.780
Micronucleos
Toxic
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
1.440
Rat (Acute)
2.280
Rat (Chronic Oral)
3.110
Fathead Minnow
4.140
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
449.990
Hydration Free Energy
-10.350
Log(D) at pH=7.4
1.220
Log(P)
0.5
Log S
-2.38
Log(Vapor Pressure)
-7.54
Melting Point
221.87
pKa Acid
7.69
pKa Basic
2.35
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9193
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9193
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9158
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9158
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9034
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9034
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9015
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9015
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8921
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8921
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8887
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8887
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8843
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8843
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8774
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8774
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8708
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8708
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8653
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8653
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8531
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8531
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8478
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8478
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8408
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8408
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8326
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8326
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8277
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8277
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8257
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8257
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8238
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8238
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.8189
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 3 0.8189
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.8069
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.8069
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.8058
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.8058
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8053
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8053
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7993
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7993
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7979
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7979
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7924
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7924
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7890
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7890
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7871
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7871
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7682
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7682
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7679
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7679
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7675
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7675
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7657
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7657
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7636
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7636
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7597
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7597
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7590
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7590
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7568
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7568
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7559
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7559
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7537
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7537
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7508
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7508
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7504
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7504
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7481
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7481
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7470
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7459
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7459
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7420
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 3 0.7420
GCN5-related N-acetyltransferase Q3M362 Q3M362_TRIV2 Trichormus variabilis 3 0.7416
GCN5-related N-acetyltransferase Q3M362 Q3M362_TRIV2 Trichormus variabilis 3 0.7416
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7411
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7411
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7377
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7377
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7376
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7376
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7353
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7353
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7301
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7301
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7281
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7281
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7275
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7275
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7241
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7241
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7235
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7235
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7217
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7217
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7215
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7207
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7207
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7194
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7194
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7186
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7186
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7177
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7177
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7159
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7159
Ribosomal RNA large subunit methyltransferase H P0C1V0 RLMH_STAAU Staphylococcus aureus 3 0.7156
Ribosomal RNA large subunit methyltransferase H P0C1V0 RLMH_STAAU Staphylococcus aureus 3 0.7156
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7149
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7149
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7132
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7132
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7115
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7115
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7103
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7103
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7095
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7095
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 3 0.7081
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 3 0.7081
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7050
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7050
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7040
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7040
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7031
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7031
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7017
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 3 0.7017
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7013
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7013
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7012
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7012

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