Butyraxanthone A - Compound Card

Butyraxanthone A

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Butyraxanthone A

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1c(O)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)C/C=C(/CCC=C(C)C)\C)O
InChI InChI=1S/C29H34O6/c1-16(2)8-7-9-18(5)11-13-19-21(30)14-24-26(27(19)32)28(33)25-20(12-10-17(3)4)29(34-6)22(31)15-23(25)35-24/h8,10-11,14-15,30-32H,7,9,12-13H2,1-6H3/b18-11+
InChIKey ABFFWBKBJIQSFF-WOJGMQOQSA-N
Formula C29H34O6
HBA 6
HBD 3
MW 478.59
Rotatable Bonds 8
TPSA 100.13
LogP 6.82
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.34
Exact Mass 478.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pentadesma butyracea Clusiaceae Plantae 198785

Showing of synonyms

  • 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: 44138727
Nmrshiftdb2: 70022000

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 478.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.33
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.240
Plasma Protein Binding
51.97
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.270
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.620
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.460
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
-183.510
Rat (Acute)
2.100
Rat (Chronic Oral)
3.370
Fathead Minnow
6.650
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
519.430
Hydration Free Energy
-3.130
Log(D) at pH=7.4
4.020
Log(P)
8.5
Log S
-6.49
Log(Vapor Pressure)
-9.22
Melting Point
177.96
pKa Acid
8.96
pKa Basic
7.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9340
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9176
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9111
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8959
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8936
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8936
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8824
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8785
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8666
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8658
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8603
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8581
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8538
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8498
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8491
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8422
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8396
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8310
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8239
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8222
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8194
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8185
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8129
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8110
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8102
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8072
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8035
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8032
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8032
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7968
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7943
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7927
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7910
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7909
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7902
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7889
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7864
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7795
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7763
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7755
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 4 0.7752
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7716
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7712
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7701
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7689
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7688
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7681
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7672
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7661
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7656
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7651
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7622
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7615
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7608
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7603
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7583
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7581
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7576
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7556
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7555
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7550
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7530
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7527
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7527
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7522
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7511
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7501
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7499
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7499
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7498
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7497
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7479
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7465
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7449
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7448
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7447
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7433
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7428
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7422
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7418
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7417
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7386
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7385
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7379
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7370
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7328
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7325
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7324
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7320
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7312
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7306
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7303
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7295
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7283
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7268
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7267
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7263
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7258
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7244
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7237
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7228
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7222
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7219
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7218
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7209
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7201
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7194
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7191
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7189
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7173
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7155
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7140
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7132
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7129
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7110
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7097
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7086
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7085
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7084
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7078
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7056
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7049
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7043
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7036
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7035
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7015
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7001

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