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Joziknipholone A
- Family: Asphodelaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Dimeric Phenylanthraquinone
| Canonical Smiles | COc1cc(O)c(c(c1C(=O)C)O)c1c(C)cc(c2c1C(=O)c1ccc(c(c1C2=O)O)[C@H]1c2cccc(c2C(=O)c2c1c(c(cc2O)C)c1c(O)cc(c(c1O)C(=O)C)OC)O)O |
|---|---|
| InChI | InChI=1S/C48H36O15/c1-16-12-24(52)39-41(30(16)37-26(54)14-28(62-5)32(18(3)49)45(37)58)34(20-8-7-9-23(51)35(20)47(39)60)21-10-11-22-36(43(21)56)48(61)40-25(53)13-17(2)31(42(40)44(22)57)38-27(55)15-29(63-6)33(19(4)50)46(38)59/h7-15,34,51-56,58-59H,1-6H3/t34-/m1/s1 |
| InChIKey | RZVXPJMOIKHWFB-UUWRZZSWSA-N |
| Formula | C48H36O15 |
| HBA | 15 |
| HBD | 8 |
| MW | 852.8 |
| Rotatable Bonds | 7 |
| TPSA | 265.65 |
| LogP | 7.2 |
| Number Rings | 8 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 63 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.15 |
| Exact Mass | 852.21 |
| Number of Lipinski Rule Violations | 4 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Bulbine frutescens | Asphodelaceae | Plantae | 210954 |
| 2 | Kniphofia foliosa | Asphodelaceae | Plantae | 214838 |
Showing of synonyms
Joziknipholone A
CHEMBL5201440
- Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [View] [PubMed]
- Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1ccccc1-c2cccc(c23)C(=O)c4c(C3=O)ccc(c4)C5c(cccc6)c6C(=O)c(c57)cccc7-c8ccccc8
Level: 3
Mol. Weight: 552.63 g/mol
SMILES: c1ccccc1-c2cccc(c23)C(=O)c4c(cccc4)C3c(c5)ccc(c56)C(=O)c7c(C6=O)cccc7
Level: 2
Mol. Weight: 476.53 g/mol
SMILES: c1ccccc1-c2cccc(c23)C(=O)c4c(C3=O)ccc(c4)C(c(c56)cccc6)c7c(C5=O)cccc7
Level: 2
Mol. Weight: 476.53 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)C(c(c45)cccc5)c6c(C4=O)cccc6
Level: 1
Mol. Weight: 400.43 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4
Level: 1
Mol. Weight: 284.31 g/mol
SMILES: c1cccc(C2=O)c1Cc(c23)c(ccc3)-c4ccccc4
Level: 1
Mol. Weight: 270.33 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 208.22 g/mol
SMILES: c1cccc(c12)Cc3c(C2=O)cccc3
Level: 0
Mol. Weight: 194.23 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
Anti-plasmodial
Antileukemia
Absorption
- Caco-2 (logPapp)
- -5.75
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 981.480
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 129132.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.150
- Plasma Protein Binding
- 91.42
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 8.120
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -3000.420
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.250
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.350
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- 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
- -234362969.670
- Rat (Acute)
- 2.470
- Rat (Chronic Oral)
- 4.600
- Fathead Minnow
- 295842.680
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 26351005.450
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.670
- Log(P)
- 8.47
- Log S
- -9.78
- Log(Vapor Pressure)
- -867699.34
- Melting Point
- 347.1
- pKa Acid
- -6281.31
- pKa Basic
- -21.14
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8700 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8700 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8675 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8675 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8609 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.8609 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8589 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8589 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8458 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8458 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.8200 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.8200 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8107 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8107 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7978 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7978 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7951 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7951 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7947 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.7947 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7757 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7757 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7708 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7708 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.7336 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.7336 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P47228 | BPHC_PARXL | Paraburkholderia xenovorans | 4 | 0.7267 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P47228 | BPHC_PARXL | Paraburkholderia xenovorans | 4 | 0.7267 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7203 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7203 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7064 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7064 |