Butyraxanthone F - Compound Card

Butyraxanthone F

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Butyraxanthone F

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Xanthone
Canonical Smiles C=CC(c1cc(OC)c(c2c1oc1c(O)cccc1c2=O)O)(C)C
InChI InChI=1S/C19H18O5/c1-5-19(2,3)11-9-13(23-4)16(22)14-15(21)10-7-6-8-12(20)17(10)24-18(11)14/h5-9,20,22H,1H2,2-4H3
InChIKey AUAJMZPJYJKEQA-UHFFFAOYSA-N
Formula C19H18O5
HBA 5
HBD 2
MW 326.35
Rotatable Bonds 3
TPSA 79.9
LogP 3.83
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 326.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentadesma butyracea Guttiferae Plantae 198785

Showing of synonyms

  • Tala M, Wabo H, et al. (2013). A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea. Phytochemistry Letters, 2013, 6(3), 326-330. [View]
Pubchem: 102442689

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 326.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.53
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.46
Plasma Protein Binding
67.99
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.48
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.53
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
3.9
Rat (Acute)
2.27
Rat (Chronic Oral)
2.48
Fathead Minnow
4.95
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
426.24
Hydration Free Energy
-9.61
Log(D) at pH=7.4
2.99
Log(P)
4.61
Log S
-5.76
Log(Vapor Pressure)
-7.62
Melting Point
150.27
pKa Acid
6.89
pKa Basic
5.26
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 0.9305
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9201
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.9064
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8942
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8901
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8891
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8836
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8765
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8671
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8566
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8545
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.8507
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8444
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.8398
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8335
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8237
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 4 0.8199
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8159
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8137
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8098
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8095
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8082
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8054
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8053
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8048
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8029
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7999
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7991
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7974
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7973
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7946
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7938
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7936
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7904
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7903
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7895
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7889
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7845
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7837
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7775
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7730
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7728
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7721
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7704
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7660
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7648
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7615
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7576
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7573
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7553
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7549
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7547
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7540
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7516
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7507
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7498
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7448
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7419
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7390
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7370
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7369
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7366
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7358
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7345
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7344
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7336
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7321
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7315
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7288
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7282
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7281
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7271
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7260
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7260
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7259
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7247
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7247
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7243
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7238
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7228
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7220
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7214
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7211
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7195
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7188
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7188
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7179
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7174
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7173
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7159
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7156
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7136
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7134
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7129
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7129
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7126
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 4 0.7111
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7098
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7079
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7064
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7051
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7048
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7041
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7038
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7024
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7018
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7018
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7005
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7004
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7000
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7000

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