2,6-Dihydroxyanthraquinone

Details

• Internal ID: 7880166f-d2aa-4099-a2fe-e2326564f901
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 2,6-dihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC2=C(C=C1O)C(=O)C3=C(C2=O)C=C(C=C3)O
• SMILES (Isomeric): C1=CC2=C(C=C1O)C(=O)C3=C(C2=O)C=C(C=C3)O
• InChI: InChI=1S/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H
• InChI Key: APAJFZPFBHMFQR-UHFFFAOYSA-N
• Popularity: 96 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: 2.20
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Anthraflavic acid
• 84-60-6
• 2,6-dihydroxyanthracene-9,10-dione
• Anthraflavin
• 9,10-Anthracenedione, 2,6-dihydroxy-
• 2,6-Dihydroxyanthra-9,10-quinone
• Az-F
• NSC-33531
• 2,6-dihydroxy-9,10-anthraquinone
• 2,6-DIHYDROXY-ANTHRAQUINONE
• 2,6-dihydroxy-9,10-anthracenedione
• Anthraflavine
• Anthraquinone, 2,6-dihydroxy-
• Anthrafravic acid
• MFCD00001228
• CCRIS 5593
• CHEBI:34250
• EINECS 201-544-3
• BRN 2054127
• CHEMBL298398
• UNII-W83883330W
• W83883330W
• 4-08-00-03272 (Beilstein Handbook Reference)
• Anthraflavic acid;2,6-Dihydroxyanthracene-9,10-dione
• ANTHRAFLAVICACID
• 9, 2,6-dihydroxy-
• 2,6dihydroxyanthraquinone
• 2,6-dihydroxyanthraquinon
• 2,6-Dihdroxyanthraquinone
• Anthraquinone,6-dihydroxy-
• Epitope ID:116189
• 2,6-dihydroxy anthraquinone
• 2,6-dihydroxy-9,10-dihydroanthracene-9,10-dione
• SCHEMBL124974
• MEGxp0_001868
• DTXSID6036546
• ACon0_001479
• ACon1_000002
• AMY2560
• 6,10-dihydroxy-2,9-anthraquinone
• 9,10-dihydroxy-2,6-anthraquinone
• NSC33531
• BDBM50101979
• s5169
• STL556593
• 2,6-dihydroxyanthracene-9.10-dione
• DIHYDROXYANTHRAQUINONE, 2,6-
• AKOS001581115
• 2,6-Dihydroxyanthra-9,10-quinone #
• CCG-266870
• CS-W006230
• HY-W006230
• Anthraflavic acid, technical grade, 90%
• NCGC00168884-01
• AS-14436
• LS-20671
• NCI60_002937
• SY049293
• EU-0066601
• FT-0699045
• L10013
• A864049
• BRD-K65281664-001-01-8
• Q27115942
• 2,6-Dihydroxyanthracene-9,10-dione;2,6-Dihydroxyanthraquinone
• InChI=1/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.7061	70.61%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8769	87.69%
OATP2B1 inhibitior	-	0.7133	71.33%
OATP1B1 inhibitior	+	0.9055	90.55%
OATP1B3 inhibitior	+	0.8968	89.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8254	82.54%
P-glycoprotein inhibitior	-	0.9393	93.93%
P-glycoprotein substrate	-	0.9743	97.43%
CYP3A4 substrate	-	0.7241	72.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7234	72.34%
CYP3A4 inhibition	-	0.8366	83.66%
CYP2C9 inhibition	+	0.7705	77.05%
CYP2C19 inhibition	-	0.6175	61.75%
CYP2D6 inhibition	-	0.7086	70.86%
CYP1A2 inhibition	+	0.8932	89.32%
CYP2C8 inhibition	-	0.9693	96.93%
CYP inhibitory promiscuity	-	0.7737	77.37%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7628	76.28%
Carcinogenicity (trinary)	Warning	0.4978	49.78%
Eye corrosion	-	0.9871	98.71%
Eye irritation	+	1.0000	100.00%
Skin irritation	+	0.6948	69.48%
Skin corrosion	-	0.9885	98.85%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8933	89.33%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.7176	71.76%
skin sensitisation	-	0.7510	75.10%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.6137	61.37%
Acute Oral Toxicity (c)	III	0.8001	80.01%
Estrogen receptor binding	+	0.8447	84.47%
Androgen receptor binding	+	0.8743	87.43%
Thyroid receptor binding	+	0.5194	51.94%
Glucocorticoid receptor binding	+	0.8993	89.93%
Aromatase binding	+	0.8514	85.14%
PPAR gamma	+	0.5897	58.97%
Honey bee toxicity	-	0.8761	87.61%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9823	98.23%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	1100 nM	IC50	PMID: 11459643
CHEMBL242	Q92731	Estrogen receptor beta	2400 nM	IC50	PMID: 11459643
CHEMBL1287617	P22309	UDP-glucuronosyltransferase 1-1	4000 nM; 3600 nM	IC50; IC50	PMID: 21030469; PMID: 21030469

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.01%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	87.67%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.14%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	84.66%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.99%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.86%	99.15%

Plants that contains it

• Reynoutria japonica
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Rubia tinctorum

Cross-Links

• PubChem: 6776
• NPASS: NPC91478
• ChEMBL: CHEMBL298398
• LOTUS: LTS0038264
• wikiData: Q27115942