1,5-dihydroxy-8-methoxyxanthone - Compound Card

1,5-dihydroxy-8-methoxyxanthone

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1,5-dihydroxy-8-methoxyxanthone

Structure
Zoomed Structure
  • Family: Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Methoxyxanthone
Canonical Smiles COc1ccc(c2c1c(=O)c1c(o2)cccc1O)O
InChI InChI=1S/C14H10O5/c1-18-9-6-5-8(16)14-12(9)13(17)11-7(15)3-2-4-10(11)19-14/h2-6,15-16H,1H3
InChIKey HUYOUKKMFHFSIU-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 roeperianum Hypericaceae Plantae —
2 Hypericum roeperianum Hypericaceae Plantae —
3 Psorospermum densipunctatum Hypericaceae Plantae 999533

Showing of synonyms

  • Demgne OMF, Damen F, et al. (2021). Botanicals and phytochemicals from the bark of Hypericum roeperianum (Hypericaceae) had strong antibacterial activity and showed synergistic effects with antibiotics against multidrug-resistant bacteria expressing active efflux pumps.. Journal of ethnopharmacology,2021, 277, 114257. [View] [PubMed]
  • Damen F, Simo Mpetga JD, et al. (2022). Roeperone A, a new tetraoxygenated xanthone and other compounds from the leaves of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2022, 36(8), 2071-2077. [View] [PubMed]
  • Sass G, Tsamo AT, et al. (2019). Vismione B Interferes with Trypanosoma cruzi Infection of Vero Cells and Human Stem Cell-Derived Cardiomyocytes.. The American journal of tropical medicine and hygiene,2019, 101(6), 1359-1368. [View] [PubMed]
Pubchem: 86088977
Nmrshiftdb2: 60070195

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 196.21 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
73.69
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
Non-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
3.980
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.200
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.140
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.700
Rat (Acute)
2.160
Rat (Chronic Oral)
2.630
Fathead Minnow
4.620
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
415.770
Hydration Free Energy
-11.030
Log(D) at pH=7.4
2.720
Log(P)
3.31
Log S
-4.37
Log(Vapor Pressure)
-7.32
Melting Point
199.52
pKa Acid
6.72
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9643
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9307
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9304
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9164
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9016
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8991
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8835
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8758
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8749
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8749
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8738
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8737
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8727
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8725
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8720
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8680
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8667
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8652
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8649
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8633
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8619
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8562
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8502
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.8472
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8445
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8397
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8311
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8238
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8236
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8171
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8105
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.8099
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8095
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8094
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8091
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8063
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8061
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8034
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8031
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8025
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7998
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7997
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7958
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7942
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7901
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7900
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7894
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7882
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7858
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7843
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7837
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7825
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7806
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7792
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7744
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7681
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7664
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7653
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7652
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7636
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7633
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7606
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7604
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7592
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7575
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7573
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7556
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7543
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7540
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7525
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7510
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7488
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7484
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7480
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7478
Ras-related protein Rap-1b P61224 RAP1B_HUMAN Homo sapiens 4 0.7474
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7447
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7443
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7442
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7440
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7439
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7438
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7427
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7404
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7400
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7395
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7372
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7342
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7337
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7328
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7323
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7312
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7296
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7294
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7282
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7271
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7260
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7259
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7249
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7244
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7243
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7243
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7241
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7239
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7236
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7227
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7223
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7206
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7205
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7197
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7190
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7186
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7184
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7182
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7178
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7175
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7174
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7173
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7155
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7147
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7127
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7123
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7122
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7116
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7107
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7103
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 3 0.7097
Dimethylglycine dehydrogenase, mitochondrial Q63342 M2GD_RAT Rattus norvegicus 4 0.7094
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7094
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7080
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7068
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7058
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7055
Aspartokinase 1, chloroplastic Q9LYU8 AK1_ARATH Arabidopsis thaliana 3 0.7048
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7038
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7032
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7029
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7029
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7028
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7027
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7027
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7025
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7012
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7011
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7003
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7002

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