Garcinone E - Compound Card

Garcinone E

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Garcinone E

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles CC(=CCc1c(O)c(O)c(c2c1c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)O)CC=C(C)C)C
InChI InChI=1S/C28H32O6/c1-14(2)7-10-17-20(29)13-21-23(24(17)30)27(33)22-18(11-8-15(3)4)25(31)26(32)19(28(22)34-21)12-9-16(5)6/h7-9,13,29-32H,10-12H2,1-6H3
InChIKey WVJYEKGQSBGNRP-UHFFFAOYSA-N
Formula C28H32O6
HBA 6
HBD 4
MW 464.56
Rotatable Bonds 6
TPSA 111.13
LogP 6.29
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 464.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pentadesma butyracea Clusiaceae Plantae 198785

Showing of synonyms

  • Lenta BN, Kamdem LM, et al. (2011). Antiplasmodial constituents from the fruit pericarp of Pentadesma butyracea.. Planta medica,2011, 77(4), 377-379. [View] [PubMed]
Pubchem: 10298511
Chebi: 185712
Nmrshiftdb2: 60030285
Bindingdb: 50242205
CPRiL: 81697
Structure

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

Level: 0

Mol. Weight: 464.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.0
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.99
Plasma Protein Binding
51.31
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
5.35
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.23
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.16
Micronucleos
Toxic
NR-AhR
Safe
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
-98.14
Rat (Acute)
2.2
Rat (Chronic Oral)
3.28
Fathead Minnow
6.05
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
547.24
Hydration Free Energy
-3.5
Log(D) at pH=7.4
3.44
Log(P)
8.13
Log S
-6.36
Log(Vapor Pressure)
-9.81
Melting Point
199.09
pKa Acid
6.49
pKa Basic
7.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8607
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8442
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8407
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8395
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8313
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8254
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8170
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7912
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7829
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7671
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7581
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7578
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7537
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7513
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7429
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7411
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7361
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7314
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 5 0.7169
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7163
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7153
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7148
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7135
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7100
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7067
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7067
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7055
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7037
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7037
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7019
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7016

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