1,8-dihydroxy-3-methoxy-6-methylxanthone - Compound Card

1,8-dihydroxy-3-methoxy-6-methylxanthone

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1,8-dihydroxy-3-methoxy-6-methylxanthone

Structure
Zoomed Structure
  • Family: Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)c(O)cc(c1)C
InChI InChI=1S/C15H12O5/c1-7-3-9(16)13-11(4-7)20-12-6-8(19-2)5-10(17)14(12)15(13)18/h3-6,16-17H,1-2H3
InChIKey QQWCJIAJCYGAIK-UHFFFAOYSA-N
Formula C15H12O5
HBA 5
HBD 2
MW 272.26
Rotatable Bonds 1
TPSA 79.9
LogP 2.67
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 272.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cassia obtusifolia Leguminosae/Fabaceae Plantae 346985

Showing of synonyms

  • Sob S, Wabo H, et al. (2010). Anthraquinones, sterols, triterpenoids and xanthones from Cassia obtusifolia. Biochemical Systematics and Ecology, 2010, 38(3), 342-345. [View]
Pubchem: 25034673
Chebi: 68287
Nmrshiftdb2: 60076495
Metabolights: MTBLC68287

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)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.320
Plasma Protein Binding
71.81
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.730
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.010
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.650
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
4.480
Rat (Acute)
2.070
Rat (Chronic Oral)
2.650
Fathead Minnow
4.660
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
414.440
Hydration Free Energy
-10.530
Log(D) at pH=7.4
3.000
Log(P)
4.03
Log S
-5.05
Log(Vapor Pressure)
-7.07
Melting Point
246.79
pKa Acid
9.05
pKa Basic
4.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9727
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9357
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9356
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9321
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9284
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9239
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9190
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9121
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.9014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8959
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8944
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8923
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8861
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8783
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8744
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8715
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8679
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8627
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8586
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8577
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8497
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8462
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8460
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8436
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8424
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8419
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8399
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8380
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8366
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8363
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8342
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.8293
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8283
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8280
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8242
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8234
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8233
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8231
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8211
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8197
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8177
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8168
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.8160
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.8081
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8079
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8077
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8073
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8069
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8069
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8067
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8048
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8032
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8013
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7986
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7971
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7955
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7890
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7877
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7836
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7834
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7833
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7810
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7788
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7780
Putative polyketide cyclase P23154 CYPC_STRCO Streptomyces coelicolor / M145) 5 0.7771
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7767
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7759
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7743
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7734
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7724
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7722
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7713
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7663
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7636
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7629
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7617
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7597
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7587
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7577
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7574
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7566
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7560
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7542
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7532
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7531
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7527
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7527
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7510
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7506
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7492
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7489
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7464
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7445
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7436
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7425
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7417
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7401
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7395
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7377
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7376
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7363
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7341
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7333
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7316
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7307
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7294
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7276
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7269
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7267
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7262
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7256
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7254
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7252
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7251
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7248
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7235
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7232
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7229
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7220
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7211
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7211
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7208
Fatty acid synthase P49327 FAS_HUMAN Homo sapiens 3 0.7207
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7204
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7192
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7179
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7178
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7178
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 3 0.7175
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7174
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7173
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7165
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7159
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7157
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7153
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7147
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7137
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 2 0.7136
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7131
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7130
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7124
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7120
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7112
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7098
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7096
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7080
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7070
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7050
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7036
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7031
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7027
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7026
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7023
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7023
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7009

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