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Kengaquinone
- Family: Plantae - Hypericaceae
- Kingdom: Plantae
- Class: Anthraquinone
| Canonical Smiles | CC(=CCC1=C(O)c2c(C(=O)C1=O)cc1c(c2O)c(O)cc(c1CC=C(C)C)C)C |
|---|---|
| InChI | InChI=1S/C25H26O5/c1-12(2)6-8-15-14(5)10-19(26)20-17(15)11-18-21(25(20)30)22(27)16(9-7-13(3)4)23(28)24(18)29/h6-7,10-11,26-27,30H,8-9H2,1-5H3 |
| InChIKey | UDPFMIAKGCOHOV-UHFFFAOYSA-N |
| Formula | C25H26O5 |
| HBA | 5 |
| HBD | 3 |
| MW | 406.48 |
| Rotatable Bonds | 4 |
| TPSA | 94.83 |
| LogP | 5.46 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.28 |
| Exact Mass | 406.18 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Harungana madagascariensis | Hypericaceae | Plantae | 198768 |
| 2 | Psorospermum aurantiacum | Hypericaceae | Plantae | 999533 |
Showing of synonyms
Kengaquinone
4,5,10-trihydroxy-7-methyl-3,8-bis(3-methylbut-2-enyl)anthracene-1,2-dione
- Kouam SF, Khan SN, et al. (2006). Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis.. Journal of natural products,2006, 69(2), 229-233. [View] [PubMed]
- Tiani G, Ahmed I, et al. (2013). Kenganthranol F, a new Anthranol from Psorospermum aurantiacum.. Natural Product Communications, 2013, 8(1), 103-104. [View] [PubMed]
Pubchem:
11509704
No compound-protein relationship available.
SMILES: O=C1C(=O)C=Cc(c12)cc3c(c2)cccc3
Level: 0
Mol. Weight: 406.48 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.99
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.8
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.5
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.13
- Plasma Protein Binding
- 53.78
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.2
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.07
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.64
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.51
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -11.11
- Rat (Acute)
- 2.4
- Rat (Chronic Oral)
- 3.32
- Fathead Minnow
- 5.13
- 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
- 492.95
- Hydration Free Energy
- -6.68
- Log(D) at pH=7.4
- 3.83
- Log(P)
- 6.63
- Log S
- -6.13
- Log(Vapor Pressure)
- -9.2
- Melting Point
- 188.65
- pKa Acid
- 6.18
- pKa Basic
- 5.22
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.9224 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8945 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8867 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8801 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8448 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.8141 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7959 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7876 |
| 3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase | P19992 | HSD_STREX | Streptomyces exfoliatus | 3 | 0.7710 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 3 | 0.7706 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7690 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7649 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7641 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7584 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7426 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7426 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7365 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7294 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7254 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7188 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7150 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7145 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7050 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7039 |
| Genome polyprotein | A0EKU1 | A0EKU1_9FLAV | Meaban virus | 3 | 0.7026 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7024 |