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Newbouldiaquinone A
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Anthraquinone
- Subclass: Naphthoquinone-Anthraquinone
| Canonical Smiles | Cc1cc2c(cc1OC1=C(O)C(=O)c3c(C1=O)cccc3)C(=O)c1c(C2=O)cccc1 |
|---|---|
| InChI | InChI=1S/C25H14O6/c1-12-10-17-18(21(27)14-7-3-2-6-13(14)20(17)26)11-19(12)31-25-23(29)16-9-5-4-8-15(16)22(28)24(25)30/h2-11,30H,1H3 |
| InChIKey | QKINIMTZORONMA-UHFFFAOYSA-N |
| Formula | C25H14O6 |
| HBA | 6 |
| HBD | 1 |
| MW | 410.38 |
| Rotatable Bonds | 2 |
| TPSA | 97.74 |
| LogP | 4.0 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.04 |
| Exact Mass | 410.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Newbouldia laevis | Bignoniaceae | Plantae | 211924 |
Showing of synonyms
Newbouldiaquinone A
2-(3-hydroxy-1,4-dioxonaphthalen-2-yl)oxy-3-methylanthracene-9,10-dione
884651-63-2
CHEMBL1909777
2-[(3-hydroxy-1,4-dioxo-2-naphthyl)oxy]-3-methyl-anthracene-9,10-dione
Pubchem:
135461057
Cas:
884651-63-2
Zinc:
ZINC000038268502
Nmrshiftdb2:
70064671
Chembl:
CHEMBL1909777
CPRiL:
69258
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC(C4=O)=CC(=O)c(c45)cccc5
Level: 1
Mol. Weight: 410.38 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 410.38 g/mol
SMILES: c1cccc(c12)C(=O)C=CC2=O
Level: 0
Mol. Weight: 410.38 g/mol
Antimalarial
Antimicrobial
Absorption
- Caco-2 (logPapp)
- -4.58
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.6
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.6
- Plasma Protein Binding
- 84.08
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Non-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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.44
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.79
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.8
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.76
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- 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
- -70.39
- Rat (Acute)
- 2.9
- Rat (Chronic Oral)
- 2.61
- Fathead Minnow
- 5.6
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 542.05
- Hydration Free Energy
- -3.01
- Log(D) at pH=7.4
- 2.5
- Log(P)
- 4.55
- Log S
- -6.08
- Log(Vapor Pressure)
- -10.83
- Melting Point
- 339.51
- pKa Acid
- 5.02
- pKa Basic
- 1.5
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9299 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.9173 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9038 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8550 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8547 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.8485 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8441 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.8358 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8330 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.8133 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8072 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8012 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7946 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 4 | 0.7937 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7873 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 5 | 0.7871 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.7815 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7801 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7793 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7724 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7653 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7650 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7568 |
| 2-Hydroxyacid oxidase 1 | Q9UJM8 | HAOX1_HUMAN | Homo sapiens | 3 | 0.7548 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7528 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7509 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7492 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7480 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7478 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7466 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7454 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7453 |
| Sodium-dependent dopamine transporter | Q7K4Y6 | DAT_DROME | Drosophila melanogaster | 2 | 0.7437 |
| Three-prime repair exonuclease 1 | Q91XB0 | TREX1_MOUSE | Mus musculus | 2 | 0.7391 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7383 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 2 | 0.7379 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7334 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7326 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7277 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7261 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7258 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7253 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7247 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7246 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7237 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7203 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7199 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7180 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7172 |
| Decaprenylphosphoryl-beta-D-ribose oxidase | I6X8C4 | I6X8C4_MYCTU | Mycobacterium tuberculosis | 3 | 0.7171 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7169 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 2 | 0.7162 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7146 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.7137 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7127 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7125 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7119 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 2 | 0.7114 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7102 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7093 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7090 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7080 |
| Metallo-beta-lactamase type 2 | P25910 | BLAB_BACFG | Bacteroides fragilis | 3 | 0.7060 |
| Sepiapterin reductase | P35270 | SPRE_HUMAN | Homo sapiens | 3 | 0.7030 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7013 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7011 |