3,6-dihydroxy-1,2-dimethoxyanthraquinone - Compound Card

3,6-dihydroxy-1,2-dimethoxyanthraquinone

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3,6-dihydroxy-1,2-dimethoxyanthraquinone

Structure
Zoomed Structure
  • Family: Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c2C(=O)c3ccc(cc3C(=O)c2cc(c1OC)O)O
InChI InChI=1S/C16H12O6/c1-21-15-11(18)6-10-12(16(15)22-2)14(20)8-4-3-7(17)5-9(8)13(10)19/h3-6,17-18H,1-2H3
InChIKey CHHCJHSDDIKETO-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 2
MW 300.27
Rotatable Bonds 2
TPSA 93.06
LogP 1.89
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
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]
Pubchem: 156025502

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 208.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.48
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
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
61.68
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
10.04
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.56
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.14
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
4.2
Rat (Acute)
2.36
Rat (Chronic Oral)
3.05
Fathead Minnow
4.52
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
434.17
Hydration Free Energy
-8.14
Log(D) at pH=7.4
2.09
Log(P)
2.58
Log S
-6.23
Log(Vapor Pressure)
-7.04
Melting Point
245.88
pKa Acid
7.07
pKa Basic
2.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9317
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9316
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9280
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9197
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9013
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8939
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8923
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8912
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8888
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8877
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8765
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8755
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.8723
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8714
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8708
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8615
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8609
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8577
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8538
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8432
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8428
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8426
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8321
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8313
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8299
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8294
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8290
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8240
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8192
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8179
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8157
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8147
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8121
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8118
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8065
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8048
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8023
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8006
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8003
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7997
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7976
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7957
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7931
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7926
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7913
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7886
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7883
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7864
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7852
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7837
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7790
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7732
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7694
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7675
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7667
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7665
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7659
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7631
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7602
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7600
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7591
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7575
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7566
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7558
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7547
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7535
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7521
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7486
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7486
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7473
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7470
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7461
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7412
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7383
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7379
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7362
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7344
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7341
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7334
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7309
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7309
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7305
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7289
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7286
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7263
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7259
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7256
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7253
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7245
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7235
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7223
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7213
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7189
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7162
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7155
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7154
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7153
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7150
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7147
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7147
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7134
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7124
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7124
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7120
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7119
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7113
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7111
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7105
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7104
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7097
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7083
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7079
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7072
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7067
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7063
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7050
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7043
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7039
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7038
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7032
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7027
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7025
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7022
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7006
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7005

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