Calyxanthone - Compound Card

Calyxanthone

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Calyxanthone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Xanthone
Canonical Smiles Oc1cc2oc3cc(C)cc(c3c(=O)c2c(c1)C(=O)O)O
InChI InChI=1S/C15H10O6/c1-6-2-9(17)13-10(3-6)21-11-5-7(16)4-8(15(19)20)12(11)14(13)18/h2-5,16-17H,1H3,(H,19,20)
InChIKey XSPSQSXYKJASKD-UHFFFAOYSA-N
Formula C15H10O6
HBA 5
HBD 3
MW 286.24
Rotatable Bonds 1
TPSA 107.97
LogP 2.36
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 286.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus wentii Trichocomaceae Fungi 5066

Showing of synonyms

  • Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]
Pubchem: 23902332
Nmrshiftdb2: 60076846

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 286.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.140
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
69.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.460
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.970
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
5.440
Rat (Acute)
1.800
Rat (Chronic Oral)
3.420
Fathead Minnow
3.920
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
468.510
Hydration Free Energy
-7.620
Log(D) at pH=7.4
0.580
Log(P)
3.35
Log S
-2.97
Log(Vapor Pressure)
-8.24
Melting Point
270.54
pKa Acid
8.45
pKa Basic
4.73
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 0.9626
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9216
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9119
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8983
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8772
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8636
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8629
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8607
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8532
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8499
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8493
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8455
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8403
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8298
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8221
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8159
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8128
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8102
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8079
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8042
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8036
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7981
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7969
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.7966
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7957
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7954
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7931
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7904
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7900
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7887
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7858
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7830
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7789
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7762
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7754
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7751
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7726
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7713
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 3 0.7708
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7658
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7559
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7525
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7519
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7513
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7507
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7463
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7452
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 4 0.7448
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7443
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7398
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7350
Stimulator of interferon genes protein Q3TBT3 STING_MOUSE Mus musculus 3 0.7331
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7317
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7307
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7300
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7299
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7297
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7281
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7252
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7245
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7238
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7233
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7209
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 3 0.7199
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7192
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7157
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7154
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7148
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7133
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7114
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7110
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7099
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7053
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7052
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7041
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7029
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7018
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7017
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7002

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