3,8-dihydroxy-6-methoxy-1-methylanthraquinone-2-carboxylic acid - Compound Card

3,8-dihydroxy-6-methoxy-1-methylanthraquinone-2-carboxylic acid

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3,8-dihydroxy-6-methoxy-1-methylanthraquinone-2-carboxylic acid

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(C)c(c(c1)O)C(=O)O
InChI InChI=1S/C17H12O7/c1-6-12-9(5-11(19)13(6)17(22)23)15(20)8-3-7(24-2)4-10(18)14(8)16(12)21/h3-5,18-19H,1-2H3,(H,22,23)
InChIKey NXISGLZWGQEYED-UHFFFAOYSA-N
Formula C17H12O7
HBA 6
HBD 3
MW 328.28
Rotatable Bonds 2
TPSA 121.13
LogP 1.89
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 328.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gladiolus segetum Iridaceae Plantae 1007786

Showing of synonyms

  • Ali AA, Abdallah M, et al. (1989). Anthraquinone derivatives from Gladiolus segetum. Phytochemistry,1989,28(1),281-282. [View]
Pubchem: 14213578
Nmrshiftdb2: 60078376

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 328.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.64
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-4.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
60.06
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
9.080
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.920
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
5.110
Rat (Acute)
2.190
Rat (Chronic Oral)
3.190
Fathead Minnow
3.890
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
498.960
Hydration Free Energy
-6.470
Log(D) at pH=7.4
0.130
Log(P)
3.73
Log S
-3.54
Log(Vapor Pressure)
-10.05
Melting Point
257.49
pKa Acid
6.18
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9426
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9426
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9350
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9350
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9284
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9284
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9155
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9155
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9151
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9151
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9097
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9097
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9087
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9087
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8921
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8921
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8882
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8882
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8746
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8746
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8707
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8707
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8686
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8686
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8650
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8650
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8624
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8624
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8603
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8603
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8602
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8602
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8601
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8601
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8577
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8577
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8529
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8529
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8524
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8524
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8353
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8353
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8301
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8301
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8279
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8279
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8239
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8239
Tryptophan synthase alpha chain P16608 TRPA_THET2 Thermus thermophilus 3 0.8220
Tryptophan synthase alpha chain P16608 TRPA_THET2 Thermus thermophilus 3 0.8220
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8219
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8219
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8208
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8208
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8172
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8172
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.8158
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.8158
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8043
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8043
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7985
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7985
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7961
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7961
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7954
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7954
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.7953
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.7953
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7949
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7949
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7938
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7938
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7920
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7920
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7915
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7915
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7895
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7895
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7870
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7870
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7861
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7861
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7811
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7811
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7743
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7743
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7694
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7694
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7691
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7691
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7555
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7555
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7536
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 3 0.7536
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7510
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7510
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7487
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7487
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7441
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7441
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7436
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7436
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7366
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7366
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7346
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7346
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7338
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7338
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7297
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7297
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7284
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7284
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7282
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7280
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7273
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7273
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7232
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7232
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7217
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7217
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7197
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7197
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7175
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7175
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7132
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7132
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7129
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7129
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7119
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7119
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7111
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7111
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7104
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7104
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7088
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7088
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7079
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7079
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7057
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7057
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7040
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7040
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7016
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7016
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7001
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7001

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