1,3,5-trihydroxy-2-methoxyxanthone - Compound Card

1,3,5-trihydroxy-2-methoxyxanthone

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1,3,5-trihydroxy-2-methoxyxanthone

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc2c(c1O)c(=O)c1c(o2)c(O)ccc1
InChI InChI=1S/C14H10O6/c1-19-14-8(16)5-9-10(12(14)18)11(17)6-3-2-4-7(15)13(6)20-9/h2-5,15-16,18H,1H3
InChIKey JAOZFCHZESUBKS-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 Pentadesma butyracea Clusiaceae Plantae 198785
2 Manilkara obovata Sapotaceae Plantae 362719

Showing of synonyms

  • Lenta BN, Kamdem LM, et al. (2011). Antiplasmodial constituents from the fruit pericarp of Pentadesma butyracea.. Planta medica,2011, 77(4), 377-379. [View] [PubMed]
  • Akosung E, Kenmogne SB, et al. (2021). Bioactive constituents from Manilkara obovata (Sabine & G.Don) J.H.Hemsl.. Natural product research,2021, 35(22), 4347-4356. [View] [PubMed]
Pubchem: 5480342
Nmrshiftdb2: 60077503
Bindingdb: 50155424

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 274.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
72.87
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
6.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.090
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
4.410
Rat (Acute)
2.280
Rat (Chronic Oral)
3.050
Fathead Minnow
4.250
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
423.790
Hydration Free Energy
-10.420
Log(D) at pH=7.4
2.330
Log(P)
2.62
Log S
-4.39
Log(Vapor Pressure)
-6.62
Melting Point
235.71
pKa Acid
6.21
pKa Basic
4.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9231
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9208
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9164
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9128
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9015
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8932
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8930
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8872
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8836
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8814
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8804
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8799
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8742
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8684
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8630
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8535
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8510
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8493
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8428
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8426
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8412
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8341
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8279
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 4 0.8250
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8235
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8234
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8183
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 4 0.8180
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8126
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.8121
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8102
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8093
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8080
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8070
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8050
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.8035
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8025
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8005
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8002
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7982
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7948
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7947
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7860
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7850
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7844
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7825
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7806
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7799
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7798
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7788
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7772
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7767
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7759
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7757
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7746
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7734
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7734
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7720
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7717
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7690
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7681
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7678
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7677
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7628
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7626
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7565
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7560
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7547
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7543
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7532
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7500
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7488
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7485
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7484
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7471
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7467
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7465
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7464
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7454
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7450
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7449
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7430
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7429
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7427
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7420
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7400
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7392
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7380
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7374
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7367
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7366
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7356
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7351
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7350
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7347
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7341
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7339
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7336
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7331
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7316
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7309
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7294
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7280
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7277
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7252
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7236
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7235
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7221
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7218
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7205
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7199
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7196
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7183
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 4 0.7177
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7167
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7165
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7159
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7155
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7151
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7130
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7125
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7119
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7119
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7109
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7107
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7099
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7092
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7084
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7069
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7067
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7056
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7052
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7050
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7048
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7044
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7043
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7040
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7039
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7038
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7035
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7029
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7017
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7013
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7007
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7006
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7004

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