1,5,7-trihydroxy-6-methoxyxanthone - Compound Card

1,5,7-trihydroxy-6-methoxyxanthone

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1,5,7-trihydroxy-6-methoxyxanthone

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Methoxyxanthone
Canonical Smiles c1(=O)c2c(cccc2oc2c(c(c(cc12)O)OC)O)O
InChI InChI=1S/C14H10O6/c1-19-14-8(16)5-6-11(17)10-7(15)3-2-4-9(10)20-13(6)12(14)18/h2-5,15-16,18H,1H3
InChIKey FWRTWVHNNCEYOG-UHFFFAOYSA-N
Formula C14H10O6
HBA 6
HBD 3
MW 274.23
Rotatable Bonds 1
TPSA 100.13
LogP 2.07
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 274.05
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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 274.23 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.97
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.17
Plasma Protein Binding
73.96
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
5.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.12
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
4.35
Rat (Acute)
2.33
Rat (Chronic Oral)
3.22
Fathead Minnow
4.27
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
424.39
Hydration Free Energy
-9.82
Log(D) at pH=7.4
2.65
Log(P)
2.42
Log S
-4.2
Log(Vapor Pressure)
-6.73
Melting Point
236.93
pKa Acid
6.83
pKa Basic
4.39
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 0.9498
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9415
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9325
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9296
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9208
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9203
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9196
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9130
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9047
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8997
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8912
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8791
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8658
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8640
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8610
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8599
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8597
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8558
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8510
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8390
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8379
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8377
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8364
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8341
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8338
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8336
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8327
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8308
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8291
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8260
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8239
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8229
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8226
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8225
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8191
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8187
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8186
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8170
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8095
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8087
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8080
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8060
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8042
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8029
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8020
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8011
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8003
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7975
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7958
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7950
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7913
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7912
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7898
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7881
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7880
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7866
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7835
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7828
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7797
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7742
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7709
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7697
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7695
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7695
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7673
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7639
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7623
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7620
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7600
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7599
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7594
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7584
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7583
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7583
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7577
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7573
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7573
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7568
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7567
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7561
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7547
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7540
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7536
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7534
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7511
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7475
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7471
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7469
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7463
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7463
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7459
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7448
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7436
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7426
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7426
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7416
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7406
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7399
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7397
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7372
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7365
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7358
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7356
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7347
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7339
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7302
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7301
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7255
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7246
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7241
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7237
Insulin receptor P06213 INSR_HUMAN Homo sapiens 4 0.7230
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7222
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7222
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7216
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7215
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7210
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7205
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7203
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7201
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7193
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7192
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7179
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7170
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7169
Dimethylglycine dehydrogenase, mitochondrial Q63342 M2GD_RAT Rattus norvegicus 4 0.7162
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7162
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7162
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7162
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7146
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7143
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7143
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7140
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7118
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7111
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7110
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7105
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7101
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7076
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7074
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7070
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7063
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7060
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7058
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7047
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7042
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7041
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7034
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7024
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7009
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7001

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