Methyl 1,8-dihydroxy-4,6,7-trimethoxy-2-naphthoate - Compound Card

Methyl 1,8-dihydroxy-4,6,7-trimethoxy-2-naphthoate

Select a section from the left sidebar

Methyl 1,8-dihydroxy-4,6,7-trimethoxy-2-naphthoate

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Naphthohydroquinone
Canonical Smiles COC(=O)c1cc(OC)c2c(c1O)c(O)c(c(c2)OC)OC
InChI InChI=1S/C15H16O7/c1-19-9-6-8(15(18)22-4)12(16)11-7(9)5-10(20-2)14(21-3)13(11)17/h5-6,16-17H,1-4H3
InChIKey WHXSAEDTQLTZPH-UHFFFAOYSA-N
Formula C15H16O7
HBA 7
HBD 2
MW 308.29
Rotatable Bonds 4
TPSA 94.45
LogP 2.06
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 308.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas bussei Rubiaceae Plantae 387051
2 Pentas bussei Rubiaceae Plantae 387051
3 Pentas bussei Rubiaceae Plantae 387051
4 Pentas parvifolia Rubiaceae Plantae 296969
5 Pentas parvifolia Rubiaceae Plantae 296969

Showing of synonyms

  • Endale M, Ekberg A, et al. (2012). Busseihydroquinones A-D from the roots of Pentas bussei. Journal of Natural Products,2012,75(7),1299-1304. [View] [PubMed]
  • 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]
  • Abdissa N, Pan F, et al. (2016). Naphthalene derivatives from the roots of Pentas parvifolia and Pentas bussei. Journal of Natural Products,2016,79(9),2181-2187. [View] [PubMed]
Pubchem: 60201020
Nmrshiftdb2: 70065307

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 308.29 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.000
Plasma Protein Binding
49.14
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.900
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.340
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.630
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
3.560
Rat (Acute)
2.230
Rat (Chronic Oral)
3.240
Fathead Minnow
4.400
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
378.670
Hydration Free Energy
-8.340
Log(D) at pH=7.4
4.120
Log(P)
2.92
Log S
-5.34
Log(Vapor Pressure)
-5.54
Melting Point
153.94
pKa Acid
7.13
pKa Basic
1.04
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 0.9368
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9368
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9315
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9315
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9286
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9286
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9108
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9108
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9102
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9101
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9101
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9089
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9089
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9079
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9079
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9046
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9046
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8903
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8903
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8829
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8829
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8825
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8825
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8704
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8704
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8508
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8508
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8494
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8494
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8429
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8429
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8381
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8381
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8331
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8331
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8323
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8323
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8287
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8287
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.8196
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 4 0.8196
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.8186
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 4 0.8186
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8168
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8168
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8158
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8158
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8152
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8152
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8101
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8101
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.8056
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.8056
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8053
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8053
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7927
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7927
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7896
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7896
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7818
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7818
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7755
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7755
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7705
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7705
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7640
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7640
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7567
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7567
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
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7451
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7451
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7440
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7440
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7419
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7419
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7326
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7326
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7320
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7320
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7319
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7319
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7291
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7291
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7277
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7277
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7264
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7264
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7254
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7254
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7235
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7235
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7220
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7220
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7193
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7193
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7186
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 0.7185
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 0.7185
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7155
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7155
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7127
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7127
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7115
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7115
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7100
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7100
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7055
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7055
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7049
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7049
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7016
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7016
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7005
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7005

Download SDF