1-hydroxy-7-methoxy-3-methylanthraquinone - Compound Card

1-hydroxy-7-methoxy-3-methylanthraquinone

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1-hydroxy-7-methoxy-3-methylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1ccc2c(c1)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C16H12O4/c1-8-5-12-14(13(17)6-8)16(19)11-7-9(20-2)3-4-10(11)15(12)18/h3-7,17H,1-2H3
InChIKey CBDWBGCZJGOSMX-UHFFFAOYSA-N
Formula C16H12O4
HBA 4
HBD 1
MW 268.27
Rotatable Bonds 1
TPSA 63.6
LogP 2.48
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 268.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cassia obtusifolia Leguminosae/Fabaceae Plantae 346985

Showing of synonyms

  • Sob S, Wabo H, et al. (2010). Anthraquinones, sterols, triterpenoids and xanthones from Cassia obtusifolia. Biochemical Systematics and Ecology, 2010, 38(3), 342-345. [View]
Pubchem: 12360346
Nmrshiftdb2: 60076491

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 268.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.430
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
57.39
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.220
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.220
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.840
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
4.750
Rat (Acute)
2.280
Rat (Chronic Oral)
2.560
Fathead Minnow
4.550
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
411.600
Hydration Free Energy
-8.570
Log(D) at pH=7.4
2.980
Log(P)
4.13
Log S
-6.41
Log(Vapor Pressure)
-6.94
Melting Point
189.5
pKa Acid
7.05
pKa Basic
4.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9685
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9456
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9334
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9154
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9134
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9131
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9100
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9013
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8869
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8808
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8722
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8656
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8655
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8556
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8556
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8515
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8486
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8391
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8342
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8259
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8254
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8245
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8171
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8142
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.8089
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8078
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8061
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8010
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8002
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7998
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7995
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7981
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7931
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7928
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7917
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7912
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7860
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7860
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7833
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7825
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7810
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7809
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7743
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7742
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7726
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7711
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7694
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7680
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7672
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7662
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7657
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7654
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7644
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7643
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7642
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7641
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7635
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7631
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7620
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7618
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7617
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7607
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7596
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7586
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7536
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7532
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7512
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7510
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7505
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7499
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7493
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7482
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7476
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7461
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7459
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7454
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7452
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7452
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 4 0.7450
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7431
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7431
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7420
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7416
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7409
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7362
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7352
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7350
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7347
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7329
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7320
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7314
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7312
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7304
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7300
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7293
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7283
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7263
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7257
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7252
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7249
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7230
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7213
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7209
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7204
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7188
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7177
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7161
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7153
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7135
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7109
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7105
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7098
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7096
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7090
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7089
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7088
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7086
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7058
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7053
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7050
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7045
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7010
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7009
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7007

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