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Quinizarine
- Family: Plantae - Verbenaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | Oc1ccc(c2c1C(=O)c1ccccc1C2=O)O |
|---|---|
| InChI | InChI=1S/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H |
| InChIKey | GUEIZVNYDFNHJU-UHFFFAOYSA-N |
| Formula | C14H8O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 240.21 |
| Rotatable Bonds | 0 |
| TPSA | 74.6 |
| LogP | 1.87 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 240.04 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tectona grandis | Verbenaceae | Plantae | 41396 |
Showing of synonyms
Quinizarine
Quinizarin
1,4-Dihydroxyanthraquinone
1,4-Dihydroxyanthra-9,10-quinone
CHEBI:37487
NSC-15367
NSC-646569
DIHYDROXYANTHRAQUINONE, 1,4-
201-368-7
81-64-1
1,4-dihydroxyanthracene-9,10-dione
Chinizarin
Solvent Orange 86
1,4-Dihydroxyanthrachinon
Smoke Orange R
1,4-Dihydroxy-9,10-anthraquinone
Macrolex Orange GG
9,10-Anthracenedione, 1,4-dihydroxy-
Anthraquinone, 1,4-dihydroxy-
1,4-Dioxyanthraquinone
103220-12-8
1,4-Doa
C.I. 58050
1,4-DIHYDROXY-9,10-ANTHRACENEDIONE
NSC 15367
NSC 646569
MFCD00001209
CHEMBL17594
8S496ZV3CS
DTXSID8044464
NSC646569
9, 1,4-dihydroxy-
1,4-dihydroxy-9,10-dihydroanthracene-9,10-dione
1,4-Dihydroxy-anthraquinone
1,4-Doa [Russian]
WLN: L C666 BV IVJ DQ GQ
CCRIS 3524
HSDB 5242
1,4-Dioxyanthraquinone [Russian]
1,4-Dihydroxyanthrachinon [Czech]
EINECS 201-368-7
UNII-8S496ZV3CS
CI 58050
AI3-17616
4,9-dihydroxy-1,10-anthraquinone
9,10-Dihydroxy-1,4-anthraquinone
Quinizarin, 96%
Solvent Orange 86
QUINIZARIN [MI]
EC 201-368-7
1,4 Dihydroxy-Anthraquinone
SCHEMBL160038
MEGxp0_001867
SCHEMBL2639287
DTXCID6024464
ACon1_000101
HY-D0226
NSC15367
NSC40899
Tox21_302041
BBL010354
BDBM50240382
CCG-48149
NSC-40899
NSC229036
STK264108
1,4-dihydroxy-anthracene-9,10-dione
AKOS001595052
1,4-Dihydroxy-9,10-anthracene-dione
1,4-Dihydroxyanthra-9,10-quinone #
9,10-Anthraquinone, 1,4-dihydroxy-
FD39689
NSC-229036
CAS-81-64-1
NCGC00160196-01
NCGC00160196-02
NCGC00255951-01
AC-11267
AS-14244
DA-57310
NCI60_001089
CS-0010138
D0243
NS00003772
F87345
EN300-6486266
AE-641/02529036
Q906609
SR-01000108129
1,4-DIHYDROXY-9,10-ANTHRACENEDIONE [HSDB]
Doi:10.14272/GUEIZVNYDFNHJU-UHFFFAOYSA-N.1
SR-01000108129-1
SR-01000637713-1
F1565-0160
1,4-Dihydroxyanthraquinone, purum, >=98.0% (HPLC), powder, red-brown
InChI=1/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16
- Kopa T, Tchinda A, et al. (2014). Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae). Phytochemistry Letters, 2014, 8, 41-45. [View]
Pubchem:
6688
Cas:
81-64-1
Zinc:
ZINC000003847495
Chebi:
37487
Nmrshiftdb2:
30100965
Chembl:
CHEMBL17594
Comptox:
DTXSID8044464
Bindingdb:
50240382
CPRiL:
66426
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 240.21 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.530
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.91
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.770
- Plasma Protein Binding
- 62.54
- 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
- Non-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
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.600
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.470
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.200
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.050
- 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
- 4.660
- Rat (Acute)
- 2.510
- Rat (Chronic Oral)
- 2.990
- Fathead Minnow
- 4.220
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 407.470
- Hydration Free Energy
- -10.430
- Log(D) at pH=7.4
- 2.290
- Log(P)
- 3.43
- Log S
- -5.79
- Log(Vapor Pressure)
- -7.79
- Melting Point
- 227.15
- pKa Acid
- 5.73
- pKa Basic
- 5.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.9547 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9412 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9329 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9286 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8903 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8819 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8717 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8708 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8526 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8385 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8330 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.8312 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.8312 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8222 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8201 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8199 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8148 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.8133 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.8032 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8024 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.8022 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7999 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7933 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7921 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7878 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7854 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7816 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7807 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7769 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 3 | 0.7740 |
| Ephrin type-B receptor 4 | P54760 | EPHB4_HUMAN | Homo sapiens | 3 | 0.7705 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7700 |
| Aurora kinase B-A | Q6DE08 | AUKBA_XENLA | Xenopus laevis | 3 | 0.7698 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7692 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7683 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7645 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7619 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7607 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 3 | 0.7596 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7594 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7593 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7541 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7529 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7514 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7507 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7498 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7479 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7467 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7458 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7432 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7427 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7420 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7416 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7397 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7396 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7387 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7381 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 4 | 0.7375 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7367 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.7362 |
| Cholinesterase | P06276 | CHLE_HUMAN | Homo sapiens | 2 | 0.7352 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7351 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7321 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7306 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 4 | 0.7303 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7303 |
| Nitric oxide synthase 1 | P29476 | NOS1_RAT | Rattus norvegicus | 4 | 0.7301 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7287 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7220 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7205 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7199 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | O02604 | DRTS_PLAVI | Plasmodium vivax | 3 | 0.7187 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7180 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 4 | 0.7167 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7145 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7138 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7135 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7132 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7126 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7117 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 2 | 0.7102 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7100 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.7092 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7079 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7078 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7076 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7066 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7055 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7053 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 3 | 0.7041 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.7039 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7034 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7028 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7027 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7017 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 2 | 0.7006 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7003 |