Select a section from the left sidebar
Gaboxanthone
- Family: Plantae - Guttiferae
- Kingdom: Plantae
- Class: Xanthone
| Canonical Smiles | COc1cc2c(c(c1OC)O)oc1c(c2=O)c(O)c2c(c1CC=C(C)C)OC(C=C2)(C)C |
|---|---|
| InChI | InChI=1S/C25H26O7/c1-12(2)7-8-14-21-13(9-10-25(3,4)32-21)18(26)17-19(27)15-11-16(29-5)24(30-6)20(28)23(15)31-22(14)17/h7,9-11,26,28H,8H2,1-6H3 |
| InChIKey | CAEVETBYJYICTB-UHFFFAOYSA-N |
| Formula | C25H26O7 |
| HBA | 7 |
| HBD | 2 |
| MW | 438.48 |
| Rotatable Bonds | 4 |
| TPSA | 98.36 |
| LogP | 5.07 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.32 |
| Exact Mass | 438.17 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Symphonia globulifera | Clusiaceae | Plantae | 156483 |
| 2 | Symphonia globulifera | Guttiferae | Plantae | 156483 |
Showing of synonyms
Gaboxanthone
5,10-dihydroxy-8,9-dimethoxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
5,10-dihydroxy-8,9-dimethoxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano(3,2-b)xanthen-6-one
876171-25-4
- Ngouela S, Lenta BN, et al. (2006). Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.. Phytochemistry,2006, 67(3), 302-306. [View] [PubMed]
- Nguengang RT, Tchegnitegni BT, et al. (2023). Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities. Molecules. 2023, 28(6), 2473. [View] [PubMed]
No compound-protein relationship available.
SMILES: O1CC=Cc(c2)c1cc(c23)oc4c(c3=O)cccc4
Level: 0
Mol. Weight: 438.48 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.820
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.380
- Plasma Protein Binding
- 55.14
- 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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.390
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.540
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.740
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.740
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -55.210
- Rat (Acute)
- 2.460
- Rat (Chronic Oral)
- 2.720
- Fathead Minnow
- 5.680
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 504.510
- Hydration Free Energy
- -3.390
- Log(D) at pH=7.4
- 3.300
- Log(P)
- 5.59
- Log S
- -6.23
- Log(Vapor Pressure)
- -8.61
- Melting Point
- 193.41
- pKa Acid
- 7.19
- pKa Basic
- 5.54
| 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 | 0.9359 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9326 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9210 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8865 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8771 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.8586 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8146 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8123 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8022 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7833 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7751 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7727 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7664 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7389 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7321 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7318 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7256 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7237 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7210 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7209 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7197 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7162 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7147 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7131 |
| Peripheral plasma membrane protein CASK | O14936 | CSKP_HUMAN | Homo sapiens | 3 | 0.7069 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7069 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7063 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7059 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7016 |