1,5,6-trihydroxy-3,7-dimethoxyxanthone - Compound Card

1,5,6-trihydroxy-3,7-dimethoxyxanthone

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1,5,6-trihydroxy-3,7-dimethoxyxanthone

Structure
Zoomed Structure
  • Family: Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)cc(c(c1O)O)OC
InChI InChI=1S/C15H12O7/c1-20-6-3-8(16)11-9(4-6)22-15-7(12(11)17)5-10(21-2)13(18)14(15)19/h3-5,16,18-19H,1-2H3
InChIKey UBCXIVCXMABZNZ-UHFFFAOYSA-N
Formula C15H12O7
HBA 7
HBD 3
MW 304.25
Rotatable Bonds 2
TPSA 109.36
LogP 2.08
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 304.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Allanblackia floribunda Guttiferae Plantae 469914

Showing of synonyms

  • Nkengfack AE, Azebaze GA, et al. (2002). A prenylated xanthone from Allanblackia floribunda.. Phytochemistry,2002, 60(4), 381-384. [View] [PubMed]
Pubchem: 5479778
Nmrshiftdb2: 70096357

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 196.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.080
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
67.84
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
6.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.870
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.720
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
4.350
Rat (Acute)
2.280
Rat (Chronic Oral)
3.060
Fathead Minnow
4.450
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
450.980
Hydration Free Energy
-9.410
Log(D) at pH=7.4
2.120
Log(P)
2.28
Log S
-4.92
Log(Vapor Pressure)
-7.04
Melting Point
228.25
pKa Acid
7.12
pKa Basic
3.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9446
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9364
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9354
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9350
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9285
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9259
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9156
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9111
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9035
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.9022
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8949
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8839
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.8780
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8710
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8700
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8681
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8660
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8654
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8619
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8610
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8596
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8571
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8571
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8528
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8526
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8493
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8493
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8391
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8362
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8323
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 4 0.8209
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8183
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8150
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8110
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8103
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8070
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8065
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8062
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8049
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8046
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8020
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7999
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7970
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7947
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7926
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7886
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7864
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7831
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7819
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7819
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7793
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7784
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7780
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7772
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7760
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7757
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7744
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7667
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7659
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7651
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7644
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7642
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7597
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7587
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7552
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7549
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7532
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7529
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7525
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7511
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7499
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7442
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7441
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7427
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7416
(6-4) photolyase A9CH39 PHRB_AGRFC Agrobacterium fabrum) 6 0.7408
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7408
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7384
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7376
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7359
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7353
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7341
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7339
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7337
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7306
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7294
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7294
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7293
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7290
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7279
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7277
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7264
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7255
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7254
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7252
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7251
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7248
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7242
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7234
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7202
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7198
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7196
NAD(P)H dehydrogenase (quinone) Q9I509 NQOR_PSEAE Pseudomonas aeruginosa 5 0.7191
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7166
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7164
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7158
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7153
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7151
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7136
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 4 0.7129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7119
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7113
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7109
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7106
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7092
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7087
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7082
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7081
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7073
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7065
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7063
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component Q6Q272 HPAH_ACIBA Acinetobacter baumannii 4 0.7060
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7056
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7049
Insulin receptor P06213 INSR_HUMAN Homo sapiens 4 0.7040
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7037
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7034
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7028
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7027
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7019
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7016
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7009
Riboflavin kinase Q969G6 RIFK_HUMAN Homo sapiens 4 0.7006
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7004

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