7-hydroxy-3-(2,3-dihydroxybutyl)-1(3H)-Isobenzofuranone - Compound Card

7-hydroxy-3-(2,3-dihydroxybutyl)-1(3H)-Isobenzofuranone

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7-hydroxy-3-(2,3-dihydroxybutyl)-1(3H)-Isobenzofuranone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Benzofuran
    • Subclass: Isobenzofuranone
Canonical Smiles CC(C(CC1OC(=O)c2c1cccc2O)O)O
InChI InChI=1S/C12H14O5/c1-6(13)9(15)5-10-7-3-2-4-8(14)11(7)12(16)17-10/h2-4,6,9-10,13-15H,5H2,1H3
InChIKey OZCHPBNVKNAWHM-UHFFFAOYSA-N
Formula C12H14O5
HBA 5
HBD 3
MW 238.24
Rotatable Bonds 3
TPSA 86.99
LogP 0.74
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 238.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus sp. Trichocomaceae Fungi —

Showing of synonyms

  • Jouda JB, Njoya EM, et al. (2023). Asperpyrone, a rare α-pyrone metabolite produced by an endophytic fungus Aspergillus sp. isolated from Garicinia smeathmannii (Planch. & Triana) Oliv.. Natural product research,2023, 37(1), 8-15. [View] [PubMed]
Pubchem: 11746674
Nmrshiftdb2: 20039295

No compound-protein relationship available.

Structure

SMILES: O=C1OCc(c12)cccc2

Level: 0

Mol. Weight: 238.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
1.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.51
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.82
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
2.53
Rat (Acute)
1.96
Rat (Chronic Oral)
2.59
Fathead Minnow
4.1
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
350.94
Hydration Free Energy
-10.34
Log(D) at pH=7.4
0.37
Log(P)
0.61
Log S
-1.71
Log(Vapor Pressure)
-6.33
Melting Point
135.04
pKa Acid
7.94
pKa Basic
2.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.9313
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9109
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8978
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8951
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8934
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8885
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8882
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8741
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8679
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8632
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8574
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8550
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8517
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8487
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8375
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8332
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8317
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8277
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8248
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8220
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8206
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8173
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8169
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8159
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.8156
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8099
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8078
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8066
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8038
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8026
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8016
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.8006
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7981
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7953
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7919
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7918
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7912
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7899
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7879
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7867
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7855
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7833
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7813
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7804
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7763
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 4 0.7740
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7740
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7700
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7649
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7591
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7588
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7574
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7544
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7544
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7538
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7529
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7525
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7519
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7512
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7510
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 4 0.7463
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7452
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7451
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 4 0.7447
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7423
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7420
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7391
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7391
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7385
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7372
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7365
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7360
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7342
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7335
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7321
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7315
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7310
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7303
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7302
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7293
Mevalonate kinase P17256 KIME_RAT Rattus norvegicus 3 0.7286
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7282
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7264
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7248
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7247
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7235
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7230
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7211
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7210
LD-carboxypeptidase A0A6L8PVW7 A0A1Q4LWC0_BACAN Bacillus anthracis 3 0.7204
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7201
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7197
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7195
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7186
Threonine--tRNA ligase editing subunit Q9YFY3 SYTE_AERPE Aeropyrum pernix 4 0.7182
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7182
HD domain protein Q836G9 Q836G9_ENTFA Enterococcus faecalis 3 0.7179
tRNA(Phe) (4-demethylwyosine(37)-C(7)) aminocarboxypropyltransferase O58523 TYW2_PYRHO Pyrococcus horikoshii 3 0.7177
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7175
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7172
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7165
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7165
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7153
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7148
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7147
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7146
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7136
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7119
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7116
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7109
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 3 0.7089
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7083
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7066
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7053
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7049
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7049
tRNA (cytosine(38)-C(5))-methyltransferase A0A2H1VE33 L7MTK8_SPOFR Spodoptera frugiperda 3 0.7047
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7035
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7034
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7019
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7014
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7010
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7009
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7007
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7002

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