7-hydroxy-methyl anthragallol 1,3-dimethyl ether - Compound Card

7-hydroxy-methyl anthragallol 1,3-dimethyl ether

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7-hydroxy-methyl anthragallol 1,3-dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles OCc1ccc2c(c1)C(=O)c1c(C2=O)cc(c(c1OC)O)OC
InChI InChI=1S/C17H14O6/c1-22-12-6-11-13(17(23-2)16(12)21)15(20)10-5-8(7-18)3-4-9(10)14(11)19/h3-6,18,21H,7H2,1-2H3
InChIKey FEPQYNZVPFDTIU-UHFFFAOYSA-N
Formula C17H14O6
HBA 6
HBD 2
MW 314.29
Rotatable Bonds 3
TPSA 93.06
LogP 1.68
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 314.08
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. (1996). Anthraquinones from the polar fractions of Galium sinaicum. Phytochemistry, 1996, 42(4), 1149-55. [View] [PubMed]
Pubchem: 15118828
Nmrshiftdb2: 70092136

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 314.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
55.3
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
8.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.22
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.39
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
2.98
Rat (Acute)
2.31
Rat (Chronic Oral)
3.12
Fathead Minnow
4.52
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
435.26
Hydration Free Energy
-8.55
Log(D) at pH=7.4
1.28
Log(P)
1.63
Log S
-5.07
Log(Vapor Pressure)
-7.4
Melting Point
186.1
pKa Acid
5.92
pKa Basic
3.82
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 0.9481
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9206
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9045
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8826
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8783
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8776
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8751
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8631
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8571
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8567
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8531
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.8454
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8429
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8394
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8320
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8301
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8223
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8154
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8135
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8111
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8109
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8058
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8051
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8042
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8028
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8019
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8004
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7956
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7949
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7947
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7893
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7877
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7849
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7829
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7823
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7805
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7723
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7630
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7592
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7582
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7579
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7577
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7575
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 5 0.7553
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7547
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7535
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7526
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7492
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7486
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7466
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7452
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7430
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7405
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7400
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7392
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7366
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7356
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7349
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7349
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7325
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7306
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7281
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7272
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7267
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7265
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.7264
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7253
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7248
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7243
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7225
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7225
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7203
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7197
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7190
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7157
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7148
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7142
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7142
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7116
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7111
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7106
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7101
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7101
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7097
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7086
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7084
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7061
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7056
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7046
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7036
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7033
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7031
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7020
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 3 0.7012
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7001

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