5-hydroxy-6-hydroxymethyl anthragallol 1,3-dimethyl ether - Compound Card

5-hydroxy-6-hydroxymethyl anthragallol 1,3-dimethyl ether

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5-hydroxy-6-hydroxymethyl anthragallol 1,3-dimethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles OCc1ccc2c(c1O)C(=O)c1c(C2=O)c(OC)c(c(c1)OC)O
InChI InChI=1S/C17H14O7/c1-23-10-5-9-12(17(24-2)16(10)22)14(20)8-4-3-7(6-18)13(19)11(8)15(9)21/h3-5,18-19,22H,6H2,1-2H3
InChIKey CIYBOVCTYRLLSS-UHFFFAOYSA-N
Formula C17H14O7
HBA 7
HBD 3
MW 330.29
Rotatable Bonds 3
TPSA 113.29
LogP 1.38
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 330.07
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. (1996). Anthraquinones from the polar fractions of Galium sinaicum. Phytochemistry, 1996, 42(4), 1149-55. [View] [PubMed]
Pubchem: 10616395
Nmrshiftdb2: 70092144

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 330.29 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
61.14
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.04
Rat (Acute)
2.35
Rat (Chronic Oral)
3.32
Fathead Minnow
4.27
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
455.01
Hydration Free Energy
-10.61
Log(D) at pH=7.4
1.5
Log(P)
1.94
Log S
-5.42
Log(Vapor Pressure)
-7.39
Melting Point
196.3
pKa Acid
5.5
pKa Basic
3.83
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 0.9461
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9327
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9041
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8830
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8785
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8754
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8751
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8725
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8723
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8630
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8566
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8461
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8421
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8258
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8203
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8143
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8055
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.8011
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8008
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7994
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7988
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7969
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7957
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7930
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7871
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7856
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7855
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7837
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7825
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7791
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7782
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7753
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7735
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7732
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7657
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7596
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7588
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7584
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7584
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7576
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7564
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7523
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7517
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7516
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7486
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7456
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7440
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7400
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7372
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7345
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7324
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 4 0.7307
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7292
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7246
dTDP-epi-vancosaminyltransferase P96558 GTFA_AMYOR Amycolatopsis orientalis 5 0.7241
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7237
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7203
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7203
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7185
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7181
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7171
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7161
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7155
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7116
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7112
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7110
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7103
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7101
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7077
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7045
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7031
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7027
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7007
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7006

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