5-acetyl-6-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran - Compound Card

5-acetyl-6-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran

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5-acetyl-6-hydroxy-2-(1-hydroxy-1-methylethyl)benzofuran

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzofuran
Canonical Smiles CC(=O)c1cc2cc(oc2cc1O)C(O)(C)C
InChI InChI=1S/C13H14O4/c1-7(14)9-4-8-5-12(13(2,3)16)17-11(8)6-10(9)15/h4-6,15-16H,1-3H3
InChIKey KIMYVHHWVJXJAN-UHFFFAOYSA-N
Formula C13H14O4
HBA 4
HBD 2
MW 234.25
Rotatable Bonds 2
TPSA 70.67
LogP 2.57
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 234.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia dracunculus Asteraceae-Compositae Plantae 72341

Showing of synonyms

  • Talbi M, Saadali B, et al. (2016). Two natural compounds – a benzofuran and a phenylpropane – from Artemisia dracunculus. Journal of Asian natural products research, 2016, 18(8), 724-9. [View] [PubMed]
Pubchem: 11139042

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 118.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.43
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
47.52
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.89
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
3.12
Rat (Acute)
2.06
Rat (Chronic Oral)
2.57
Fathead Minnow
4.17
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
337.09
Hydration Free Energy
-11.6
Log(D) at pH=7.4
2.26
Log(P)
2.28
Log S
-3.17
Log(Vapor Pressure)
-6.15
Melting Point
169.23
pKa Acid
7.43
pKa Basic
4.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9338
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9038
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8997
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8990
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8983
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8960
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8938
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8859
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8681
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8674
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8630
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8516
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8338
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8284
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8273
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.8235
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 3 0.8234
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8200
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 3 0.8120
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8104
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8081
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8080
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8076
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8051
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8045
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.7985
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7979
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7964
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7963
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7949
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7942
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7864
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7864
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7844
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7838
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7818
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7808
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7806
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7780
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7764
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7760
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7755
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7741
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7738
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7704
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7688
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7671
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7650
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7642
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7634
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7631
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7599
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7545
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7543
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7541
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7537
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7513
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7494
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7490
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7489
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7485
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7475
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7473
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7466
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7465
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7447
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7439
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7416
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7409
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7398
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7397
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7390
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7381
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7375
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7339
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7335
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7329
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7324
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7295
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7293
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7263
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7261
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7248
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7236
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7236
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7235
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7233
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7231
MutT/nudix family protein O33199 O33199_MYCTO Mycobacterium tuberculosis 3 0.7226
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7225
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7213
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7196
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7195
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7187
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7169
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7158
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7153
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7144
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7141
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7122
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7116
DNA ligase P15042 DNLJ_ECOLI Escherichia coli 4 0.7114
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7109
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7106
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7103
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7102
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7083
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7081
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7080
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7071
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7064
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7049
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7016
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7015
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7010
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7007
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7003

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