1,3,6-trihydroxy-2-methoxyanthraquinone - Compound Card

1,3,6-trihydroxy-2-methoxyanthraquinone

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1,3,6-trihydroxy-2-methoxyanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c(O)cc2c(c1O)C(=O)c1c(C2=O)cc(cc1)O
InChI InChI=1S/C15H10O6/c1-21-15-10(17)5-9-11(14(15)20)13(19)7-3-2-6(16)4-8(7)12(9)18/h2-5,16-17,20H,1H3
InChIKey XUHCTZUMZGBPRV-UHFFFAOYSA-N
Formula C15H10O6
HBA 6
HBD 3
MW 286.24
Rotatable Bonds 1
TPSA 104.06
LogP 1.59
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 286.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morinda lucida Rubiaceae Plantae 339305

Showing of synonyms

  • Longue Ekon J, Zra T, et al. (2020). New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters, 2020, 39, 94-98. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 286.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
68.73
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.440
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.420
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
4.310
Rat (Acute)
2.520
Rat (Chronic Oral)
3.330
Fathead Minnow
4.220
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
433.620
Hydration Free Energy
-8.300
Log(D) at pH=7.4
2.060
Log(P)
2.59
Log S
-5.79
Log(Vapor Pressure)
-6.91
Melting Point
268.85
pKa Acid
6.85
pKa Basic
3.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9115
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9101
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9101
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9026
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8940
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8926
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8896
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8818
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8809
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8754
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8723
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8711
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8703
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8650
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8648
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8642
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8545
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8510
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8508
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8416
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.8415
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8390
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8389
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8345
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8343
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8338
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8313
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8311
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8298
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8280
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8266
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8247
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8235
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8223
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8118
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.8112
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8100
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8099
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8097
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8005
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7965
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7960
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7929
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7924
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7914
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7914
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7905
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7902
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7886
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7841
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7823
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 5 0.7809
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7757
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7737
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7735
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7735
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7723
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7687
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7679
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7677
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7660
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7660
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7654
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7633
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7612
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7591
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7591
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7576
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7576
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7570
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7553
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7537
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7501
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7493
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7475
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7463
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7457
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7452
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7451
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7446
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7439
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7438
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7411
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7407
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7403
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7398
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7395
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7369
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7366
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7355
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7349
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7302
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7283
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7280
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7277
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7256
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7248
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7225
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7210
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7198
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7197
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7196
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7196
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7188
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7182
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7165
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7162
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7161
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7141
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7132
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7128
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7125
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7120
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7116
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7096
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7092
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7091
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7089
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7087
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7080
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7069
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7047
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7035
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7023
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7020
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7008

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