1,5-dihydroxy-2-methoxyxanthone - Compound Card

1,5-dihydroxy-2-methoxyxanthone

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1,5-dihydroxy-2-methoxyxanthone

Structure
Zoomed Structure
  • Family: Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Xanthone Derivative
Canonical Smiles COc1ccc2c(c1O)c(=O)c1c(o2)c(O)ccc1
InChI InChI=1S/C14H10O5/c1-18-10-6-5-9-11(13(10)17)12(16)7-3-2-4-8(15)14(7)19-9/h2-6,15,17H,1H3
InChIKey IWDZOJJDTFMEHP-UHFFFAOYSA-N
Formula C14H10O5
HBA 5
HBD 2
MW 258.23
Rotatable Bonds 1
TPSA 79.9
LogP 2.37
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 258.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum riparium Hypericaceae Plantae 269018

Showing of synonyms

  • Tala MF, Talontsi FM, et al. (2015). Antimicrobial and cytotoxic constituents from native Cameroonian medicinal plant Hypericum riparium.. Fitoterapia,2015, 102, 149-155. [View] [PubMed]
Pubchem: 5377509
Nmrshiftdb2: 70076771

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 196.21 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.620
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
75.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
4.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.650
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.220
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.990
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
4.730
Rat (Acute)
2.040
Rat (Chronic Oral)
2.730
Fathead Minnow
4.530
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
407.810
Hydration Free Energy
-11.080
Log(D) at pH=7.4
2.720
Log(P)
3.1
Log S
-4.69
Log(Vapor Pressure)
-6.89
Melting Point
194.58
pKa Acid
5.42
pKa Basic
4.48
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9468
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9430
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9306
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9157
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.9036
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9003
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8937
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8909
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8893
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8889
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8841
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8840
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8835
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8829
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8750
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8744
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8726
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8635
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8630
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8627
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8576
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8563
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.8543
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.8518
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8516
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8504
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8416
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8408
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8408
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8278
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8235
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8218
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8176
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8148
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8145
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8112
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8109
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8093
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8089
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8089
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8086
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8029
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8007
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.8006
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8004
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7990
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7972
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7966
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7961
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7947
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7883
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7859
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7844
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7828
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7820
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7811
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7794
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7792
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7784
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7760
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7756
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7727
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7696
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7696
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7692
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7683
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7674
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7669
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7656
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7648
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7635
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7635
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7627
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7616
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7584
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7580
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7566
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7528
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7519
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7518
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7500
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7499
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7480
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7471
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7471
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7463
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7457
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7455
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7446
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7432
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7432
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7430
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7429
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7418
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7416
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7410
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7410
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7409
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7400
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7391
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7385
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7371
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7368
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7367
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7366
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7359
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7352
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7340
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 4 0.7338
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7315
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7310
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7306
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7302
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7301
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7299
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7293
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7282
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7267
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7255
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7248
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7246
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7232
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7228
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7221
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7210
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7209
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7204
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7203
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7188
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7176
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7169
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7166
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7151
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7151
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7146
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7145
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7137
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7135
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7128
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7126
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7117
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7111
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7096
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7096
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7090
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7086
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7071
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7059
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7051
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7046
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7045
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7044
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7039
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7028
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7015
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7013
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7012
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7001

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