Anthragallol 1,3-dimethyl ether - Compound Card

Anthragallol 1,3-dimethyl ether

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Anthragallol 1,3-dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1c2C(=O)c3ccccc3C(=O)c2cc(c1OC)O
InChI InChI=1S/C16H12O5/c1-20-15-11(17)7-10-12(16(15)21-2)14(19)9-6-4-3-5-8(9)13(10)18/h3-7,17H,1-2H3
InChIKey HVGBWHWYZSXFQX-UHFFFAOYSA-N
Formula C16H12O5
HBA 5
HBD 1
MW 284.27
Rotatable Bonds 2
TPSA 72.83
LogP 2.18
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

  • Halim A, Abd El-Fattah H, et al. (1992). Anthraquinones from Galium sinaicum. Phytochemistry, 1992, 31(1), 355-356. [View]
Pubchem: 57509304
Nmrshiftdb2: 60079538

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)
-4.48
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.38
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
61.04
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
7.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.21
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
3.92
Rat (Acute)
2.44
Rat (Chronic Oral)
2.65
Fathead Minnow
4.69
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
401.03
Hydration Free Energy
-7.39
Log(D) at pH=7.4
1.86
Log(P)
2.93
Log S
-5.42
Log(Vapor Pressure)
-6.68
Melting Point
204.73
pKa Acid
6.51
pKa Basic
1.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9761
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9353
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9325
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9317
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9316
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9144
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.9133
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9014
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8988
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8913
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8890
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8877
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8760
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8714
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8707
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8695
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8650
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8634
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8627
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8614
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8585
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8570
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8553
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8473
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8470
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8340
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8294
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8267
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8251
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8221
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8193
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8192
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8180
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8125
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8125
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8094
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8089
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8062
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8040
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8016
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8006
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8004
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7991
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7959
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7928
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7921
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7914
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7888
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7859
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7852
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7845
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7828
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7795
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7778
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7747
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7732
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7695
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7671
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7636
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7625
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7598
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7597
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7592
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7581
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7548
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7545
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7538
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7535
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7523
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7517
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7505
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7499
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7499
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7495
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7489
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7488
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7481
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7480
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 0.7470
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7463
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7428
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7423
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7418
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7418
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7410
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7405
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7401
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7388
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7387
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7381
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7376
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7369
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7366
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7349
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7342
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7338
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7312
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7311
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7310
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7287
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7282
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7279
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7269
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7267
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7263
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7262
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7255
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7250
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7248
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7248
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7238
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7237
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7228
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7216
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7206
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7200
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7193
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7189
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7187
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7181
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7178
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7176
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7162
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7158
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7156
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7156
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7152
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7151
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7149
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7144
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7133
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7130
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7128
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7124
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7122
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7120
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7120
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7111
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7111
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7110
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7109
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7105
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7101
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7097
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7089
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7085
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7073
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7072
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7068
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7058
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7046
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7036
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7029
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7018
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7012
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7007
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7000

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