6-methylanthragallol 3-methyl ether - Compound Card

6-methylanthragallol 3-methyl ether

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6-methylanthragallol 3-methyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1cc2C(=O)c3cc(C)ccc3C(=O)c2c(c1O)O
InChI InChI=1S/C16H12O5/c1-7-3-4-8-9(5-7)13(17)10-6-11(21-2)15(19)16(20)12(10)14(8)18/h3-6,19-20H,1-2H3
InChIKey INLJMGJYPZLNJN-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: 9971104

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)
-4.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
66.95
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
7.600
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.560
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
4.340
Rat (Acute)
2.590
Rat (Chronic Oral)
3.020
Fathead Minnow
4.490
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
408.890
Hydration Free Energy
-7.440
Log(D) at pH=7.4
1.810
Log(P)
2.98
Log S
-5.75
Log(Vapor Pressure)
-7.38
Melting Point
219.78
pKa Acid
5.64
pKa Basic
4.38
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 0.9686
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9175
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9133
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9120
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9060
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9056
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8997
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8977
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8925
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8921
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8775
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8754
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8753
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8699
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8663
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8626
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8606
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8599
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8580
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8516
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8463
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8413
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8345
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8331
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8319
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8298
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8275
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8267
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8231
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8181
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8173
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8131
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8122
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8105
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8084
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8048
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8035
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8023
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8018
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7969
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7943
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7931
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7900
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7885
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7856
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.7847
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7782
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7754
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7743
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7704
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7652
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7640
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7631
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7599
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7596
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7589
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7577
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7565
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7539
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7536
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7529
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7516
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7507
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7492
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7451
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7444
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7432
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7406
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7404
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7400
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7397
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 4 0.7393
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7376
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7374
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7371
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7359
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7355
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7339
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7320
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7311
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7306
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7305
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7304
Bifunctional F420 biosynthesis protein FbiB P9WP79 FBIB_MYCTU Mycobacterium tuberculosis 5 0.7296
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7296
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7284
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7266
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7260
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7260
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7256
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7244
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7242
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7240
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7240
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 4 0.7236
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7221
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7216
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7200
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7163
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7150
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7148
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7143
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7136
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7115
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7100
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7099
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7097
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7093
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7092
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7081
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7068
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7064
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7061
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7060
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7058
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7039
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7034
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7030
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7029
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7024
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7022
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7013
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7010

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