Rubraxanthone - Compound Card

Rubraxanthone

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Rubraxanthone

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc2c(c1C/C=C(/CCC=C(C)C)\C)c(=O)c1c(o2)cc(cc1O)O
InChI InChI=1S/C24H26O6/c1-13(2)6-5-7-14(3)8-9-16-21-20(12-18(27)24(16)29-4)30-19-11-15(25)10-17(26)22(19)23(21)28/h6,8,10-12,25-27H,5,7,9H2,1-4H3/b14-8+
InChIKey JLTSTSRANGPLOQ-RIYZIHGNSA-N
Formula C24H26O6
HBA 6
HBD 3
MW 410.47
Rotatable Bonds 6
TPSA 100.13
LogP 5.31
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 410.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pentadesma butyracea Clusiaceae Plantae 198785
2 Allanblackia floribunda Guttiferae Plantae 469914

Showing of synonyms

  • Azebaze AG, Teinkela JE, et al. (2015). Antiplasmodial activity of some phenolic compounds from Cameroonians Allanblackia.. African health sciences,2015, 15(3), 835-840. [View] [PubMed]
  • Zelefack F, Guilet D, et al. (2009). Cytotoxic and antiplasmodial xanthones from Pentadesma butyracea.. Journal of natural products,2009, 72(5), 954-957. [View] [PubMed]
Pubchem: 9953366
Chebi: 66318
Nmrshiftdb2: 60030286
Metabolights: MTBLC66318

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 410.47 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.34
Human Oral Bioavailability 20%
Non-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
-0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
58.65
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.740
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.770
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.690
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-14.750
Rat (Acute)
2.160
Rat (Chronic Oral)
3.420
Fathead Minnow
5.940
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
490.870
Hydration Free Energy
-7.400
Log(D) at pH=7.4
3.540
Log(P)
6.22
Log S
-6.02
Log(Vapor Pressure)
-8.72
Melting Point
195.73
pKa Acid
8.87
pKa Basic
6.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9231
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9201
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9198
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.9096
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9068
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8948
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8882
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8845
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8780
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8763
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8758
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8756
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8735
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8640
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8544
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8522
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8521
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8502
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8501
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8491
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8469
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8453
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8444
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8436
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.8423
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8421
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8408
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8347
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8340
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8327
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8316
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8301
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8299
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8297
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8291
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8261
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8257
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8241
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8220
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8160
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.8153
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8125
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8103
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8088
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8085
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8074
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8073
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8068
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8049
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8021
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8015
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8000
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7967
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7962
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7960
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7955
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7915
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7915
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7846
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7831
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7815
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7800
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7789
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7772
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7765
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7744
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7740
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7731
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7730
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7715
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7713
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7703
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7702
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7685
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7685
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7682
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7678
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7672
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7665
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7642
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7623
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7617
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7616
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7610
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7575
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7573
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7571
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7564
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7523
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7510
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7499
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7499
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7486
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7483
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7466
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7465
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7459
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7442
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7441
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7437
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7426
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7423
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7410
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7406
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7386
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7383
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7374
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7370
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7362
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7348
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7341
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7334
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7326
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7318
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7317
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7310
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7308
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7306
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 4 0.7296
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7293
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7289
NAD(P)H dehydrogenase (quinone) Q9I509 NQOR_PSEAE Pseudomonas aeruginosa 5 0.7287
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7285
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7284
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7284
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7274
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7274
Diguanylate phosphodiesterase A6T8V8 A6T8V8_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7267
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7259
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7259
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7248
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7243
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7232
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7222
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7199
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 4 0.7191
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7176
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7171
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7161
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7154
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7150
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7126
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7120
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7101
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7088
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7086
Dihydroorotate dehydrogenase B (NAD(+)), catalytic subunit P54322 PYRDB_LACLM Lactococcus lactis subsp. cremoris 5 0.7067
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7064
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7060
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 4 0.7052
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7052
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7042
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7030
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7027
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7013
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7008
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7003

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