Garcinone E - Compound Card

Garcinone E

Select a section from the left sidebar

Garcinone E

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles CC(=CCc1c(O)c(CC=C(C)C)c(c2c1oc1c(O)ccc(c1c2=O)O)O)C
InChI InChI=1S/C23H24O6/c1-11(2)5-7-13-19(26)14(8-6-12(3)4)22-18(20(13)27)21(28)17-15(24)9-10-16(25)23(17)29-22/h5-6,9-10,24-27H,7-8H2,1-4H3
InChIKey OJXQLGQIDIPMTE-UHFFFAOYSA-N
Formula C23H24O6
HBA 6
HBD 4
MW 396.44
Rotatable Bonds 4
TPSA 111.13
LogP 4.79
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 396.16
Number of Lipinski Rule Violations 0
# 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: 5281633
Kegg Ligand: C10063
Chebi: 5279
Nmrshiftdb2: 60025320
Metabolights: MTBLC5279
Bindingdb: 50311743
CPRiL: 81697
Structure

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

Level: 0

Mol. Weight: 396.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
58.22
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
4.67
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.78
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.29
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
-5.87
Rat (Acute)
2.34
Rat (Chronic Oral)
3.27
Fathead Minnow
5.3
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
509.11
Hydration Free Energy
-8.99
Log(D) at pH=7.4
3.25
Log(P)
6.48
Log S
-6.0
Log(Vapor Pressure)
-8.8
Melting Point
196.87
pKa Acid
6.08
pKa Basic
6.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9121
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8908
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8905
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8773
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8718
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.8479
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8423
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8175
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8093
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8016
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7976
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7943
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7895
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7864
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7821
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7711
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7642
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7553
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7525
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7517
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7516
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7470
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7455
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7439
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7438
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7437
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7396
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7392
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7385
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7358
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7330
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7319
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7317
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7314
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7245
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7241
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7236
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7220
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7166
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7111
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7087
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7084
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7080
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7070
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7053
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7039
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7030
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7005

Download SDF