Quinalizarin

Details

• Internal ID: 710e0780-c09b-4a77-9000-df2315af9129
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,2,5,8-tetrahydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C2=C1C(=O)C3=C(C=CC(=C3C2=O)O)O)O)O
• InChI: InChI=1S/C14H8O6/c15-6-3-4-7(16)11-10(6)12(18)5-1-2-8(17)13(19)9(5)14(11)20/h1-4,15-17,19H
• InChI Key: VBHKTXLEJZIDJF-UHFFFAOYSA-N
• Popularity: 567 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₆
• Molecular Weight: 272.21 g/mol
• Exact Mass: 272.03208797 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.28
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• 81-61-8
• 1,2,5,8-Tetrahydroxyanthraquinone
• Alizarinbordeaux
• 1,2,5,8-tetrahydroxyanthracene-9,10-dione
• Alizarine Bordeaux B
• Khinalizarin
• Quinalizarine
• Alizarine Bordeaux
• 1,4,5,6-Tetrahydroxyanthraquinone
• C.I. Mordant Violet 26
• 1,2,5,8-Tetrahydroxy-9,10-anthraquinone
• Alizarin Bordeaux BD
• C.I. 58500
• 9,10-Anthracenedione, 1,2,5,8-tetrahydroxy-
• 1,2,5,8-Tetrahydroxy-9,10-anthracenedione
• NSC 144046
• Anthraquinone, 1,2,5,8-tetrahydroxy-
• 1,2,5,8-Tetrahydroxyanthracinon
• NSC 4896
• 1,2,5,8-Tetrahydroxy anthraquinone
• CCRIS 5598
• NSC4896
• EINECS 201-366-6
• UNII-6D43C3LYSG
• BRN 1889617
• 6D43C3LYSG
• CHEMBL29898
• 1,2,5,8-Tetrahydroxyanthra-9,10-quinone
• CHEBI:37495
• NSC-4896
• 1,2,5,8-Tetrahydroxy-Anthraquinone
• NSC-144046
• 4-08-00-03683 (Beilstein Handbook Reference)
• 1,5,8-Tetrahydroxyanthracinon
• 9, 1,2,5,8-tetrahydroxy-
• 1,5,8-Tetrahydroxyanthraquinone
• 1,2,5,8-tetrahydroxy-9,10-dihydroanthracene-9,10-dione
• Anthraquinone,2,5,8-tetrahydroxy-
• 1,5,8-Tetrahydroxy-9,10-anthraquinone
• Alizarinbordeux
• Chinalizarin
• Quinalizarin, E
• PHF 016
• TXQ
• Mordant Violet 26
• MFCD00001205
• QUINAZARIN
• Spectrum_000952
• 3fl5
• Spectrum2_001362
• Spectrum3_000778
• Spectrum4_000998
• Spectrum5_000846
• QUINALIZARIN [MI]
• D0Q0MM
• D0X7HJ
• BSPBio_002456
• KBioGR_001435
• KBioSS_001432
• DivK1c_000144
• SCHEMBL138122
• SPECTRUM1500759
• SPBio_001284
• DTXSID4052558
• HMS500H06
• KBio1_000144
• KBio2_001432
• KBio2_004000
• KBio2_006568
• KBio3_001676
• Quinalizarin, >=95% (HPLC)
• NINDS_000144
• VBHKTXLEJZIDJF-UHFFFAOYSA-N
• 1,2,5,8-tetrahydroxyanthraquinon
• HMS1923K15
• BBL012309
• BDBM50041419
• CCG-38979
• NSC144046
• STK803167
• AKOS004901435
• DB08660
• 1, 2, 5, 8-Tetrahydroxyanthraquinone
• IDI1_000144
• NCGC00095268-01
• NCGC00095268-02
• NCGC00095268-03
• LS-20711
• NCI60_004175
• VS-03274
• 1,5,8,10-tetrahydroxy-2,9-anthraquinone
• 2,5,8,9-tetrahydroxy-1,10-anthraquinone
• 2,8,9,10-tetrahydroxy-1,5-anthraquinone
• 4,5,6,9-tetrahydroxy-1,10-anthraquinone
• 4,7,8,9-tetrahydroxy-1,10-anthraquinone
• 4,8,9,10-tetrahydroxy-1,7-anthraquinone
• 5,6,9,10-tetrahydroxy-1,4-anthraquinone
• 5,8,9,10-tetrahydroxy-1,2-anthraquinone
• HY-124833
• FT-0606262
• 1,2,5,8-Tetrahydroxyanthra-9,10-quinone #
• 3,4-Dihydro-4-oxo-5-quinazolinecarboxylicacid
• A840172
• SR-01000196297
• Q1073575
• SR-01000196297-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9746	97.46%
Caco-2	-	0.8548	85.48%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7846	78.46%
OATP2B1 inhibitior	-	0.6821	68.21%
OATP1B1 inhibitior	+	0.9429	94.29%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8646	86.46%
P-glycoprotein inhibitior	-	0.9580	95.80%
P-glycoprotein substrate	-	0.9651	96.51%
CYP3A4 substrate	-	0.6898	68.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8234	82.34%
CYP3A4 inhibition	-	0.9015	90.15%
CYP2C9 inhibition	+	0.6130	61.30%
CYP2C19 inhibition	-	0.8994	89.94%
CYP2D6 inhibition	-	0.8724	87.24%
CYP1A2 inhibition	+	0.8636	86.36%
CYP2C8 inhibition	-	0.9576	95.76%
CYP inhibitory promiscuity	-	0.8609	86.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8675	86.75%
Carcinogenicity (trinary)	Warning	0.5731	57.31%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.9793	97.93%
Skin irritation	+	0.7820	78.20%
Skin corrosion	-	0.9068	90.68%
Ames mutagenesis	+	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8741	87.41%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.7555	75.55%
skin sensitisation	+	0.4909	49.09%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.6634	66.34%
Acute Oral Toxicity (c)	III	0.5724	57.24%
Estrogen receptor binding	+	0.7261	72.61%
Androgen receptor binding	+	0.6296	62.96%
Thyroid receptor binding	-	0.5609	56.09%
Glucocorticoid receptor binding	+	0.9199	91.99%
Aromatase binding	+	0.5740	57.40%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.9259	92.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9862	98.62%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	6309.6 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	251.2 nM; 251.2 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	31622.8 nM	Potency	via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	31622.8 nM	Potency	via CMAUP
CHEMBL3629	P68400	Casein kinase II alpha	60 nM	Ki	via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 6309.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	563 nM	IC50	via Super-PRED
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	3981.1 nM	Potency	via CMAUP
CHEMBL3587	Q02750	Dual specificity mitogen-activated protein kinase kinase 1	3548.1 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	5011.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3548.1 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	3162.3 nM; 7943.3 nM; 10000 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	2511.9 nM; 1412.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	25118.9 nM; 44668.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1000 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	3981.1 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.37%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.89%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.10%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.88%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.29%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.11%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.95%	96.67%
CHEMBL3194	P02766	Transthyretin	82.89%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.55%	99.23%

Plants that contains it

• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 5004
• NPASS: NPC147418
• ChEMBL: CHEMBL29898