7-methylanthragallol 1,3-dimethyl ether - Compound Card

7-methylanthragallol 1,3-dimethyl ether

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7-methylanthragallol 1,3-dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1c(O)c(OC)cc2c1C(=O)c1cc(C)ccc1C2=O
InChI InChI=1S/C17H14O5/c1-8-4-5-9-10(6-8)15(19)13-11(14(9)18)7-12(21-2)16(20)17(13)22-3/h4-7,20H,1-3H3
InChIKey QWWWXMJAWBZPLB-UHFFFAOYSA-N
Formula C17H14O5
HBA 5
HBD 1
MW 298.29
Rotatable Bonds 2
TPSA 72.83
LogP 2.49
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 298.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Galium sinaicum Rubiaceae Plantae 25168

Showing of synonyms

  • El-Gamal A.A, Takeya K, et al. (1992). Anthraquinones from Galium sinaicum. Phytochemistry, 1992, 31(1), 355-360. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 298.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.030
Plasma Protein Binding
61.28
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.850
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
3.940
Rat (Acute)
2.440
Rat (Chronic Oral)
2.740
Fathead Minnow
4.700
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
410.880
Hydration Free Energy
-6.970
Log(D) at pH=7.4
2.110
Log(P)
2.8
Log S
-5.82
Log(Vapor Pressure)
-6.96
Melting Point
204.28
pKa Acid
6.16
pKa Basic
3.45
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 0.9571
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9481
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9168
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9136
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9045
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8928
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8803
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8775
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8757
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8711
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8631
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8594
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8576
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8556
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8555
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8429
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8407
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8390
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8305
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8196
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8183
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8138
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8126
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8123
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8123
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8122
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8103
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8096
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8089
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8066
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8044
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8006
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8006
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7999
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7984
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.7974
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7958
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7954
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7947
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7909
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7877
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7876
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7859
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7837
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7810
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7795
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7780
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7774
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7723
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7722
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7714
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7705
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7686
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7657
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7652
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7638
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7632
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7599
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7584
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7582
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7576
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7575
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7545
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7526
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7524
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7522
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7517
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7513
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7505
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7503
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7486
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7477
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7475
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7457
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7453
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7440
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7435
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7413
AppA, antirepressor of ppsR, sensor of blue light Q3J677 Q3J677_RHOS4 Rhodobacter sphaeroides 5 0.7412
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7362
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7351
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7333
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7326
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7321
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7281
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 4 0.7273
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7261
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7259
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7259
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7242
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7236
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7228
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7195
Flavodoxin 1 P61949 FLAV_ECOLI Escherichia coli 6 0.7188
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7182
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7179
Isopentenyl-diphosphate delta-isomerase P61615 IDI2_SACSH Saccharolobus shibatae 6 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7172
Ferric-chelate reductase (NAD(P)H) O29428 FERCR_ARCFU Archaeoglobus fulgidus 6 0.7164
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7145
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7142
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7140
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7136
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 3 0.7121
Protein-tyrosine kinase 2-beta Q14289 FAK2_HUMAN Homo sapiens 4 0.7120
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7120
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7107
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7106
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7104
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7103
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7063
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7047
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7038
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7038
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7035
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7034
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7032
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7032
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7022
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7021
Ferric-chelate reductase (NAD(P)H) O29428 FERCR_ARCFU Archaeoglobus fulgidus 6 0.7020
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7019
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 4 0.7018
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7018
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7017
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7009
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7002
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7002

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