4-hydroxy-1,3-dimethoxyxanthone - Compound Card

4-hydroxy-1,3-dimethoxyxanthone

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4-hydroxy-1,3-dimethoxyxanthone

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Xanthone Derivative
Canonical Smiles c1(=O)c2c(cc(c(c2oc2ccccc12)O)OC)OC
InChI InChI=1S/C15H12O5/c1-18-10-7-11(19-2)14(17)15-12(10)13(16)8-5-3-4-6-9(8)20-15/h3-7,17H,1-2H3
InChIKey XXWWXKFWYAFNSV-UHFFFAOYSA-N
Formula C15H12O5
HBA 5
HBD 1
MW 272.26
Rotatable Bonds 2
TPSA 68.9
LogP 2.67
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 272.07
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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 272.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.25
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.51
Plasma Protein Binding
76.61
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.92
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
4.11
Rat (Acute)
2.09
Rat (Chronic Oral)
2.53
Fathead Minnow
4.93
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
393.46
Hydration Free Energy
-9.03
Log(D) at pH=7.4
1.92
Log(P)
2.67
Log S
-4.66
Log(Vapor Pressure)
-6.6
Melting Point
171.96
pKa Acid
6.24
pKa Basic
2.46
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 0.9655
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9433
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9431
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9327
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9294
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9274
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9228
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9191
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9153
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9108
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9070
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9061
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8979
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8964
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8949
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8930
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8925
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8897
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8782
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8772
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8751
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8743
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8714
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8703
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8703
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8699
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8641
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8615
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8599
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8572
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8563
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8557
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8556
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8502
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8495
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8482
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8432
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8393
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8386
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8374
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8333
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8320
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8319
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8308
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8267
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8204
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8202
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8134
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8131
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8103
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.8079
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8051
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8041
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8023
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.8017
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7974
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7970
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7970
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7881
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7872
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7821
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7818
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7815
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7815
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7813
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7774
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7773
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7772
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7767
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7750
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7735
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7732
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7723
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7705
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7700
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7688
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7682
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7674
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7664
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7659
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7646
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7645
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7623
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7618
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7585
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7574
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7569
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7559
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7553
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7551
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7551
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7551
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7529
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7527
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7514
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7496
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7495
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7492
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7487
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7482
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 3 0.7481
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7471
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7468
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7468
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7461
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7448
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7445
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7431
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7423
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7413
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7412
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7410
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7409
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7400
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7397
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7392
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7389
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7382
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7375
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7372
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7342
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7337
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7335
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7329
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7318
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7309
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7307
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7294
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7288
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7288
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7284
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7280
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7276
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7268
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7267
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7232
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7232
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7229
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7224
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7222
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7210
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7200
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7196
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7195
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7194
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7186
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7183
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7178
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7169
Tyrosine-protein kinase receptor TYRO3 P55144 TYRO3_MOUSE Mus musculus 3 0.7168
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7166
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7155
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7133
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7118
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7109
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7101
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7101
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7085
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7066
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7060
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7055
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7054
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7052
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7041
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7021
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7016
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7005

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