1,3,5-trihydroxyxanthone - Compound Card

1,3,5-trihydroxyxanthone

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1,3,5-trihydroxyxanthone

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles Oc1cc(O)c2c(c1)oc1c(c2=O)cccc1O
InChI InChI=1S/C13H8O5/c14-6-4-9(16)11-10(5-6)18-13-7(12(11)17)2-1-3-8(13)15/h1-5,14-16H
InChIKey XESIWQIMUSNPRO-UHFFFAOYSA-N
Formula C13H8O5
HBA 5
HBD 3
MW 244.2
Rotatable Bonds 0
TPSA 90.9
LogP 2.06
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 244.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Garcinia polyantha Guttiferae Plantae 469941

Showing of synonyms

  • Louh GN, Lannang AM, et al. (2008). Polyanxanthone A, B and C, three xanthones from the wood trunk of Garcinia polyantha Oliv.. Phytochemistry,2008, 69(4), 1013-1017. [View] [PubMed]
Pubchem: 5281663
Kegg Ligand: C10094
Chebi: 514
Nmrshiftdb2: 60029554
Metabolights: MTBLC514
Bindingdb: 50155436

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 244.2 g/mol

Anticholinesterase

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
73.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.77
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.27
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.46
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.24
Rat (Acute)
2.0
Rat (Chronic Oral)
3.0
Fathead Minnow
4.33
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
431.45
Hydration Free Energy
-12.32
Log(D) at pH=7.4
2.86
Log(P)
2.83
Log S
-3.98
Log(Vapor Pressure)
-7.73
Melting Point
279.34
pKa Acid
4.72
pKa Basic
7.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9436
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9270
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9270
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9247
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9216
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9013
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8942
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8914
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8893
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8840
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8836
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8786
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8779
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8765
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8762
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8741
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8721
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8675
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8672
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8646
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8644
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8614
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8613
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8551
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8515
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8435
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8419
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 4 0.8395
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8394
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8357
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8354
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8345
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.8340
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8318
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8316
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8261
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 4 0.8259
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.8231
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8230
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8203
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8135
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8115
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8108
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8077
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8074
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8066
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8060
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8042
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8021
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8006
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7996
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7967
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7958
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7954
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7935
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7931
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7927
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7925
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7895
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7891
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7885
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7877
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7876
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7876
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7862
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7853
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7852
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7827
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7791
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7788
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7777
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7766
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7745
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7709
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7701
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7693
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7680
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7671
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7661
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7658
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7650
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7609
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7606
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7599
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7576
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7568
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7548
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7547
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7542
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7539
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7523
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7505
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7493
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7475
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7469
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7464
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7457
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7434
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7423
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7418
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7398
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7391
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7391
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7389
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7387
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7384
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7380
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7359
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7359
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7356
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7350
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7343
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7336
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7332
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7316
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7313
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7295
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7290
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7283
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7281
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7274
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7270
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7264
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7264
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7249
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7243
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7242
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7240
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7234
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7228
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7227
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7226
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7221
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7219
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7219
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7205
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7203
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7200
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7200
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7188
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7176
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7172
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7163
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7152
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7141
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7141
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7128
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7120
Adenosine receptor A2a P29274 AA2AR_HUMAN Homo sapiens 4 0.7108
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7107
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7104
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7099
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7098
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7096
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7076
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7075
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7074
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7066
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7064
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7062
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7062
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7061
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7061
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7049
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7046
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7042
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7034
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7028
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7026
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7018
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7013
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7007
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7007

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