Methyl 8-hydroxy-1,4,6,7-tetramethoxy-2-naphthoate - Compound Card

Methyl 8-hydroxy-1,4,6,7-tetramethoxy-2-naphthoate

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Methyl 8-hydroxy-1,4,6,7-tetramethoxy-2-naphthoate

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Naphthalene Derivative
Canonical Smiles COC(=O)c1cc(OC)c2c(c1OC)c(O)c(c(c2)OC)OC
InChI InChI=1S/C16H18O7/c1-19-10-7-9(16(18)23-5)14(21-3)12-8(10)6-11(20-2)15(22-4)13(12)17/h6-7,17H,1-5H3
InChIKey UTWVKRMPKJSGEW-UHFFFAOYSA-N
Formula C16H18O7
HBA 7
HBD 1
MW 322.31
Rotatable Bonds 5
TPSA 83.45
LogP 2.37
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 322.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas bussei Rubiaceae Plantae 387051

Showing of synonyms

  • Bukuru J, De Kimpe N, et al. (2003). Isolation and structural elucidation of natural products from Pentas bussei K. Krause, Pentas lanceolata (Forsk.) Deflers and Pentas parvifolia Hiern (Rubiaceae). Ph.D. Thesis, University of Ghent, Faculty of Bioscience Engineering, Belgium,2003. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 322.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
40.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
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
4.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.930
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.160
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.950
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
3.110
Rat (Acute)
2.260
Rat (Chronic Oral)
2.880
Fathead Minnow
4.750
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.530
Hydration Free Energy
-7.390
Log(D) at pH=7.4
4.210
Log(P)
2.76
Log S
-4.3
Log(Vapor Pressure)
-6.13
Melting Point
132.98
pKa Acid
7.77
pKa Basic
-0.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9481
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9481
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9324
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9324
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9314
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9314
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9171
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9171
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9130
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9130
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9111
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9111
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9110
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9110
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9081
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9081
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9036
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9036
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9019
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9019
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8995
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8995
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8965
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8965
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8911
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8911
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8893
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8893
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8797
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8797
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8791
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8791
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8751
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8751
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8734
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8734
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8662
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8662
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8516
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8516
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8479
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8479
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8457
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8457
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8376
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8376
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8286
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8286
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8275
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8275
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8242
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8242
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8194
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8194
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.8182
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.8182
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.8166
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.8166
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8011
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8011
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7986
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7986
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7972
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7972
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7866
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7866
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7821
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7821
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7799
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7799
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7796
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7796
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7735
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7735
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7646
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7646
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7629
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7629
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7583
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7583
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7576
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7576
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7543
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7543
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7525
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7525
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7521
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7521
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7467
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7467
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7447
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7447
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7437
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7437
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7386
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7386
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7376
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7376
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7355
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7355
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 3 0.7340
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 3 0.7340
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7319
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7319
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7313
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7313
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7303
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7303
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7292
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7292
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7279
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7279
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7270
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7259
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7259
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7238
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7238
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7218
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7218
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7199
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7199
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7190
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7190
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7163
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7163
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7148
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7148
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7141
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7141
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7128
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7128
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7096
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7096
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7076
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7065
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7065
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7029
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7029
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7026
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7026
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7025
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7025

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