6-hydroxyanthragallol 1,3-dimethyl ether - Compound Card

6-hydroxyanthragallol 1,3-dimethyl ether

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6-hydroxyanthragallol 1,3-dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1cc2C(=O)c3cc(O)ccc3C(=O)c2c(c1O)OC
InChI InChI=1S/C16H12O6/c1-21-11-6-10-12(16(22-2)15(11)20)14(19)8-4-3-7(17)5-9(8)13(10)18/h3-6,17,20H,1-2H3
InChIKey ZOTYVTMFTQVAFY-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 Galium sinaicum Rubiaceae Plantae 25168
2 Galium sinaicum Rubiaceae Plantae 25168

Showing of synonyms

  • Halim A, Abd El-Fattah H, et al. (1992). Anthraquinones from Galium sinaicum. Phytochemistry, 1992, 31(1), 355-356. [View]
  • El-Gamal A.A, Takeya K, et al. (1996). Anthraquinones from the polar fractions of Galium sinaicum. Phytochemistry, 1996, 42(4), 1149-55. [View] [PubMed]
Pubchem: 15118826
Nmrshiftdb2: 70014156

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.4
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
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)
0.960
Plasma Protein Binding
59.78
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
9.830
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.400
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.990
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
4.160
Rat (Acute)
2.390
Rat (Chronic Oral)
3.080
Fathead Minnow
4.510
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
433.520
Hydration Free Energy
-8.380
Log(D) at pH=7.4
2.010
Log(P)
2.18
Log S
-6.46
Log(Vapor Pressure)
-7.15
Melting Point
237.04
pKa Acid
6.21
pKa Basic
3.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9478
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9263
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9211
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9123
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9095
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9045
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9021
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8989
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8930
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8802
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8748
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8713
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8690
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8678
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8631
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8548
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8458
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8440
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8429
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8384
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8374
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8342
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8325
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8225
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8222
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8185
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8182
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8171
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8157
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8120
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8104
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.8093
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8086
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8010
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7995
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7980
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7977
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7974
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7954
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7950
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7906
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7898
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7875
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7863
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7856
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7838
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7825
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7815
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7804
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7754
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7742
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7737
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7720
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7695
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7643
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7640
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7614
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7612
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7583
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7581
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7575
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7567
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7561
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7552
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7539
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7527
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7509
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7507
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7496
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7486
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7460
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7458
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7448
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7426
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7408
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7382
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7371
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7369
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7352
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7337
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7337
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7333
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7327
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7279
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7263
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7254
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7244
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7227
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7224
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7201
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7201
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7199
dTDP-epi-vancosaminyltransferase P96558 GTFA_AMYOR Amycolatopsis orientalis 5 0.7192
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7181
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7175
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7162
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7152
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7147
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7139
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7134
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7132
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7120
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7110
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7106
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7104
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7104
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7080
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7077
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7076
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7064
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7052
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7050
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7012
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7012
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7006

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