1-hydroxy-2-methoxyanthraquinone - Compound Card

1-hydroxy-2-methoxyanthraquinone

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1-hydroxy-2-methoxyanthraquinone

Structure
Zoomed Structure
  • Family: Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1ccc2c(c1O)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C15H10O4/c1-19-11-7-6-10-12(15(11)18)14(17)9-5-3-2-4-8(9)13(10)16/h2-7,18H,1H3
InChIKey BYQWRZGQEZAOPQ-UHFFFAOYSA-N
Formula C15H10O4
HBA 4
HBD 1
MW 254.24
Rotatable Bonds 1
TPSA 63.6
LogP 2.18
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 254.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas schimperi Rubiaceae Plantae 25384

Showing of synonyms

  • Goffin E, Ziemons E, et al. (2002). In vitro antiplasmodial activity of Tithonia diversifolia and identification of its main active constituent: tagitinin C.. Planta medica,2002, 68(6), 543-545. [View] [PubMed]
Pubchem: 80103
Kegg Ligand: C10291
Chebi: 2575
Nmrshiftdb2: 60027350

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 208.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.370
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
59.5
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
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
6.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.270
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.230
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
4.210
Rat (Acute)
2.460
Rat (Chronic Oral)
2.700
Fathead Minnow
4.540
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
390.990
Hydration Free Energy
-7.040
Log(D) at pH=7.4
2.160
Log(P)
3.55
Log S
-5.58
Log(Vapor Pressure)
-7.06
Melting Point
190.7
pKa Acid
5.97
pKa Basic
3.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9614
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9482
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9455
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9338
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9297
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9225
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9182
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9111
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9063
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9062
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8960
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8941
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8908
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8848
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8802
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8713
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8635
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8606
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8571
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8497
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8428
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8387
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8343
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8298
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8295
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8284
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8278
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8275
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8236
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8231
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8201
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8180
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8143
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8111
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8058
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.8024
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7971
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7911
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7891
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7882
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7865
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7833
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7829
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7813
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7811
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7810
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7792
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7758
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7735
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7729
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7703
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7702
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7680
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7671
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7649
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7620
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7618
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7599
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7599
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7597
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7574
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7539
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7534
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7530
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7526
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7500
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7460
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7448
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7444
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7427
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7423
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7395
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7383
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7382
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7381
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7381
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7380
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7379
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7367
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7364
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7364
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7363
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7358
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7355
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7350
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7342
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7331
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7323
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7304
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7293
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7292
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7290
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7280
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7280
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7278
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7250
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7246
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7243
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7243
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7233
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7232
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7220
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7208
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7206
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7200
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7198
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7190
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7183
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7178
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7176
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7166
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7163
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7163
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7157
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7156
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7149
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7144
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7130
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7121
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7117
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7106
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7105
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7102
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7094
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7092
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7081
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7076
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7070
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7070
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7062
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7050
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7042
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7037
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7025
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7025
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7019
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7005

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