7-methyl-anthragallol 2-methyl ether - Compound Card

7-methyl-anthragallol 2-methyl ether

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7-methyl-anthragallol 2-methyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1c(O)cc2c(c1O)C(=O)c1c(C2=O)ccc(c1)C
InChI InChI=1S/C16H12O5/c1-7-3-4-8-9(5-7)14(19)12-10(13(8)18)6-11(17)16(21-2)15(12)20/h3-6,17,20H,1-2H3
InChIKey QZWWTQJLGUJNEA-UHFFFAOYSA-N
Formula C16H12O5
HBA 5
HBD 2
MW 284.27
Rotatable Bonds 1
TPSA 83.83
LogP 2.19
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 284.07
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]
Pubchem: 69164487

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 284.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.43
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
67.72
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
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
7.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.830
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
4.000
Rat (Acute)
2.590
Rat (Chronic Oral)
3.090
Fathead Minnow
4.410
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
401.660
Hydration Free Energy
-7.320
Log(D) at pH=7.4
2.410
Log(P)
3.24
Log S
-5.99
Log(Vapor Pressure)
-7.04
Melting Point
227.8
pKa Acid
6.58
pKa Basic
3.69
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 0.9445
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9259
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9156
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.9061
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9026
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8878
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8843
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8817
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8810
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8792
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8730
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8714
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8690
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8662
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8616
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8548
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8534
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8530
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8468
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8415
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8368
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8353
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8340
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8336
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8271
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8227
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8208
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8196
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8178
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8154
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8148
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8131
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8123
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8117
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8103
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8100
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8008
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8000
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7994
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7965
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7964
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7930
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7911
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7902
Bifunctional dihydrofolate reductase-thymidylate synthase Q27783 DRTS_TRYBB Trypanosoma brucei brucei 5 0.7857
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7853
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7840
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7835
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7823
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7816
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7816
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7793
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7786
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7778
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7770
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7759
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7751
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 5 0.7705
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7699
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7696
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7696
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7684
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7672
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7646
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7625
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7623
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7621
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7594
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7574
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7546
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7519
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7514
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7497
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7485
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7482
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7481
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.7476
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7475
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7473
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7472
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7468
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7465
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7451
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7447
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7442
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7419
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7414
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7409
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7405
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7402
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7398
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7386
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7376
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7376
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7371
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7356
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7353
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7338
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7302
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7265
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7265
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7220
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7219
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7212
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7211
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7206
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7204
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7193
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7191
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7190
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7187
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7164
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7153
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7148
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7141
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7127
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7127
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7126
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7117
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7111
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7102
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7091
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7082
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7076
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7073
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7071
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7059
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7052
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7036
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7016
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7006

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