3,4,5-trihydroxyacetophenone - Compound Card

3,4,5-trihydroxyacetophenone

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3,4,5-trihydroxyacetophenone

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles CC(=O)c1cc(O)c(c(c1)O)O
InChI InChI=1S/C8H8O4/c1-4(9)5-2-6(10)8(12)7(11)3-5/h2-3,10-12H,1H3
InChIKey IBKQQKPQRYUGBJ-UHFFFAOYSA-N
Formula C8H8O4
HBA 4
HBD 3
MW 168.15
Rotatable Bonds 1
TPSA 77.76
LogP 1.01
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 168.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia gaditana Euphorbiaceae Plantae 3990

Showing of synonyms

  • Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
Pubchem: 36586

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 168.15 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
36.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
12.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.02
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.75
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.54
Micronucleos
Toxic
NR-AhR
Toxic
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
3.35
Rat (Acute)
1.94
Rat (Chronic Oral)
3.0
Fathead Minnow
3.85
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
335.33
Hydration Free Energy
-12.68
Log(D) at pH=7.4
0.1
Log(P)
0.23
Log S
-1.15
Log(Vapor Pressure)
-4.65
Melting Point
180.95
pKa Acid
6.76
pKa Basic
7.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9417
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9367
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9258
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9241
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9228
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9212
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9210
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9142
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9120
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8876
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8826
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8782
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8777
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8762
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8760
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8759
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8739
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8719
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8687
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8677
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8629
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8607
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8586
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.8565
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.8560
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8531
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8522
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8508
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8505
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8478
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8439
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8418
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8385
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.8368
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8363
Purine nucleoside phosphorylase P9WP00 PUNA_MYCTO Mycobacterium tuberculosis 4 0.8337
Glycogen synthase P0A6U8 GLGA_ECOLI Escherichia coli 3 0.8318
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8291
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8262
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8217
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8093
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 4 0.8085
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8059
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8044
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8040
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.8035
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 4 0.8026
S-methyl-5'-thioinosine phosphorylase Q9HZK1 MTIP_PSEAE Pseudomonas aeruginosa 4 0.7973
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7844
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7785
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7777
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7776
Uracil-DNA glycosylase P20536 UNG_VACCC Vaccinia virus 4 0.7747
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7740
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7694
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7677
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7655
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7620
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7595
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7591
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7586
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7581
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7554
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7536
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7514
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7505
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7493
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7490
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7456
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7436
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7415
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7411
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7392
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 4 0.7389
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7388
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7341
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7335
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7295
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7295
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7292
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7279
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7262
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7261
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7260
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7250
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 4 0.7244
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7244
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.7235
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7232
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7225
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7223
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7219
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7214
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7202
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7194
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7186
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7172
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7170
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7161
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7158
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7155
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7145
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7143
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7142
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7133
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7133
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7114
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7104
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7099
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7083
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7079
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7076
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7066
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7062
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7048
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7038
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7019
Ribosomal RNA small subunit methyltransferase Nep1 Q57977 NEP1_METJA Methanocaldococcus jannaschii 3 0.7014
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7009
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7004

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