Quinizarin

Details

• Internal ID: ebdfacdb-feb9-4d42-9f63-255b49025e48
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1,4-dihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)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
• InChI Key: GUEIZVNYDFNHJU-UHFFFAOYSA-N
• Popularity: 499 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21 g/mol
• Exact Mass: 240.04225873 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 1,4-Dihydroxyanthraquinone
• 81-64-1
• 1,4-dihydroxyanthracene-9,10-dione
• Quinizarine
• 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-
• 1,4-Dihydroxyanthra-9,10-quinone
• Anthraquinone, 1,4-dihydroxy-
• 1,4-Dioxyanthraquinone
• 1,4-Doa
• 1,4-Dihydroxy-anthraquinone
• C.I. 58050
• 1,4-Doa [Russian]
• 103220-12-8
• 1,4-DIHYDROXY-9,10-ANTHRACENEDIONE
• NSC 15367
• NSC 646569
• CCRIS 3524
• CHEBI:37487
• HSDB 5242
• 1,4-Dioxyanthraquinone [Russian]
• 1,4-Dihydroxyanthrachinon [Czech]
• EINECS 201-368-7
• NSC-15367
• NSC-646569
• UNII-8S496ZV3CS
• CI 58050
• CHEMBL17594
• AI3-17616
• 8S496ZV3CS
• DTXSID8044464
• 9,10-Dihydroxy-1,4-anthraquinone
• DIHYDROXYANTHRAQUINONE, 1,4-
• NSC646569
• 9, 1,4-dihydroxy-
• EC 201-368-7
• WLN: L C666 BV IVJ DQ GQ
• Quinzarine
• 4,9-dihydroxy-1,10-anthraquinone
• Quinizarin, 96%
• MFCD00001209
• Quinizarin (Sublimed)
• QUINIZARIN [MI]
• 1,4-dihydroxyanthraquinon
• 1,4 dihydroxyanthraquinone
• D0Y6OK
• 1,4 Dihydroxy-Anthraquinone
• SCHEMBL160038
• MEGxp0_001867
• SCHEMBL2639287
• DTXCID6024464
• ACon1_000101
• 1,4-Dihydroxyanthraquinone(Crude)
• HY-D0226
• NSC15367
• NSC40899
• Tox21_302041
• BBL010354
• BDBM50240382
• CCG-48149
• NSC-40899
• NSC229036
• STK264108
• 9,10-antraquinona, 1,4-dihidroxi-
• 1,4-dihydroxy-anthracene-9,10-dione
• AKOS001595052
• 1,4-Dihydroxy-9,10-anthracene-dione
• 1,4-Dihydroxyanthra-9,10-quinone #
• NSC-229036
• Quinizarin; 1,4-Dihydroxyanthraquinone
• CAS-81-64-1
• NCGC00160196-01
• NCGC00160196-02
• NCGC00255951-01
• AC-11267
• AS-14244
• LS-20669
• NCI60_001089
• CS-0010138
• D0243
• FT-0657575
• F87345
• EN300-6486266
• A840176
• AE-641/02529036
• Q906609
• SR-01000108129
• 1,4-DIHYDROXY-9,10-ANTHRACENEDIONE [HSDB]
• 1,4-dihydroxy-9,10-dihydroanthracene-9,10-dione
• SR-01000108129-1
• SR-01000637713-1
• W-104202
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	-	0.6158	61.58%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8545	85.45%
OATP2B1 inhibitior	-	0.7214	72.14%
OATP1B1 inhibitior	+	0.9633	96.33%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8976	89.76%
P-glycoprotein inhibitior	-	0.9268	92.68%
P-glycoprotein substrate	-	0.9934	99.34%
CYP3A4 substrate	-	0.7441	74.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.8357	83.57%
CYP2C9 inhibition	+	0.7750	77.50%
CYP2C19 inhibition	-	0.6159	61.59%
CYP2D6 inhibition	-	0.7456	74.56%
CYP1A2 inhibition	+	0.8918	89.18%
CYP2C8 inhibition	-	0.9789	97.89%
CYP inhibitory promiscuity	-	0.7605	76.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7609	76.09%
Carcinogenicity (trinary)	Warning	0.5038	50.38%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.9783	97.83%
Skin irritation	+	0.7507	75.07%
Skin corrosion	-	0.9842	98.42%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8900	89.00%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.8000	80.00%
skin sensitisation	-	0.7890	78.90%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.7791	77.91%
Acute Oral Toxicity (c)	III	0.5401	54.01%
Estrogen receptor binding	+	0.7843	78.43%
Androgen receptor binding	+	0.6656	66.56%
Thyroid receptor binding	-	0.5638	56.38%
Glucocorticoid receptor binding	+	0.9216	92.16%
Aromatase binding	+	0.6953	69.53%
PPAR gamma	+	0.8508	85.08%
Honey bee toxicity	-	0.8582	85.82%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9793	97.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 1995.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.91%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	93.48%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.48%	99.15%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.22%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.74%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.70%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	80.89%	94.73%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.43%	93.03%
CHEMBL2535	P11166	Glucose transporter	80.25%	98.75%

Plants that contains it

• Galium sinaicum
• Reynoutria japonica
• Rubia tinctorum
• Senna obtusifolia

Cross-Links

• PubChem: 6688
• NPASS: NPC96915
• ChEMBL: CHEMBL17594
• LOTUS: LTS0023479
• wikiData: Q906609