1,6-dihydroxy-2,3,5-trimethoxy-8-methyl-9H-xanthen-9-one - Compound Card

1,6-dihydroxy-2,3,5-trimethoxy-8-methyl-9H-xanthen-9-one

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1,6-dihydroxy-2,3,5-trimethoxy-8-methyl-9H-xanthen-9-one

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc2oc3c(OC)c(O)cc(c3c(=O)c2c(c1OC)O)C
InChI InChI=1S/C17H16O7/c1-7-5-8(18)15(22-3)17-11(7)13(19)12-9(24-17)6-10(21-2)16(23-4)14(12)20/h5-6,18,20H,1-4H3
InChIKey YMJKCJXHXKSOLV-UHFFFAOYSA-N
Formula C17H16O7
HBA 7
HBD 2
MW 332.31
Rotatable Bonds 3
TPSA 98.36
LogP 2.69
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 332.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ledebouria ovatifolia Hyacinthaceae Plantae 1069013

Showing of synonyms

  • Waller CP, Thumser AE, et al. (2013). COX-2 inhibitory activity of homoisoflavanones and xanthones from the bulbs of the Southern African Ledebouria socialis and Ledebouria ovatifolia (Hyacinthaceae: Hyacinthoideae). Phytochemistry, 2013, 95, 284–290. [View]
Pubchem: 162864727

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 332.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
68.32
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
5.900
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.000
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
3.580
Rat (Acute)
2.070
Rat (Chronic Oral)
2.630
Fathead Minnow
4.910
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
449.970
Hydration Free Energy
-9.630
Log(D) at pH=7.4
2.410
Log(P)
3.14
Log S
-4.74
Log(Vapor Pressure)
-7.01
Melting Point
200.88
pKa Acid
6.3
pKa Basic
3.38
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 0.9386
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9304
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9185
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.9058
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9010
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8991
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8904
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8851
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8831
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8806
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8803
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8737
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8722
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8687
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8686
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 4 0.8645
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8624
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8526
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8484
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8442
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8440
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8439
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8419
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8406
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8289
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8244
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8220
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8220
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8218
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8201
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8161
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8145
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8071
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8070
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8062
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8056
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8010
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8008
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8005
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8002
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7996
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7981
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7972
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7944
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7925
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7881
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7871
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7870
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7797
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7776
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7769
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7765
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7718
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7710
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7677
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7658
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7637
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7630
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7607
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7575
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7563
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7553
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7535
Riboflavin kinase Q969G6 RIFK_HUMAN Homo sapiens 4 0.7527
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7512
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7500
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7499
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7498
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7480
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7467
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7466
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7458
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7449
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7446
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7446
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7421
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7400
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7397
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7388
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7365
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7351
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7336
mitogen-activated protein kinase kinase Q7YTF7 Q7YTF7_PLAF7 Plasmodium falciparum 4 0.7333
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7332
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7330
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7321
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7316
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7310
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7295
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7283
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7280
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7276
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 5 0.7246
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7242
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7241
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7241
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7235
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7232
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7216
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7212
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7208
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7199
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7153
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7149
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7130
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7124
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7112
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7111
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7109
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7099
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7095
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7092
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7091
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7069
NADPH--cytochrome P450 reductase P00388 NCPR_RAT Rattus norvegicus 4 0.7054
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7051
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7031
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7024
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7021
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7019
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7008

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