2-Hydroxyanthraquinone

Details

• Internal ID: c5cfa2c2-ee2b-42fc-a7dc-6030893318b9
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 2-hydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)O
• InChI: InChI=1S/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15H
• InChI Key: GCDBEYOJCZLKMC-UHFFFAOYSA-N
• Popularity: 61 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈O₃
• Molecular Weight: 224.21 g/mol
• Exact Mass: 224.047344113 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 605-32-3
• 2-hydroxyanthracene-9,10-dione
• 2-Hydroxy-9,10-anthraquinone
• Anthraquinone, 2-hydroxy-
• 9,10-Anthracenedione, 2-hydroxy-
• beta-Hydroxyanthraquinone
• 2-Hydroxy-9,10-anthracenedione
• CCRIS 9186
• CHEBI:37482
• NSC 2595
• EINECS 210-085-8
• .beta.-Hydroxyanthraquinone
• 2-Hydroxyanthra-9,10-quinone
• DTXSID4049327
• NSC-2595
• HYDROXY-9,10-ANTHRACENEDIONE
• 2R8351U6Q0
• 27938-76-7
• 9, 2-hydroxy-
• 2-hydroxy-anthraquinone
• Hydroxyanthraquinone, 2-
• SCHEMBL498619
• CHEMBL446963
• DTXCID3029283
• UNII-2R8351U6Q0
• 10-hydroxy-2,9-anthra-quinone
• 9,10-Anthracenedione,2-hydroxy
• NSC2595
• 2-Hydroxyanthra-9,10-quinone #
• 2-hydroxyanthraquinone, AldrichCPR
• BCP24349
• Tox21_202901
• BDBM50025601
• MFCD00027374
• AKOS001588311
• CS-W013068
• HY-W012352
• NCGC00260447-01
• BS-17188
• CAS-605-32-3
• LS-20687
• PD151278
• EU-0033611
• FT-0612578
• H1012
• D78173
• W-109568
• Q27117163
• TERT-BUTYL3-(2-AMINOETHYL)-5-CHLOROPHENYLCARBAMATE
• InChI=1/C14H8O3/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,15

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5965	59.65%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8690	86.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8368	83.68%
P-glycoprotein inhibitior	-	0.9255	92.55%
P-glycoprotein substrate	-	0.9643	96.43%
CYP3A4 substrate	-	0.6695	66.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7234	72.34%
CYP3A4 inhibition	-	0.9296	92.96%
CYP2C9 inhibition	+	0.5438	54.38%
CYP2C19 inhibition	-	0.7306	73.06%
CYP2D6 inhibition	-	0.7546	75.46%
CYP1A2 inhibition	+	0.9207	92.07%
CYP2C8 inhibition	-	0.9250	92.50%
CYP inhibitory promiscuity	-	0.8580	85.80%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7528	75.28%
Carcinogenicity (trinary)	Warning	0.5370	53.70%
Eye corrosion	-	0.9770	97.70%
Eye irritation	+	0.9917	99.17%
Skin irritation	+	0.7604	76.04%
Skin corrosion	-	0.9913	99.13%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.9119	91.19%
Micronuclear	+	0.5198	51.98%
Hepatotoxicity	+	0.7750	77.50%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.6845	68.45%
Acute Oral Toxicity (c)	III	0.6708	67.08%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8967	89.67%
Thyroid receptor binding	+	0.5325	53.25%
Glucocorticoid receptor binding	+	0.8173	81.73%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.5663	56.63%
Honey bee toxicity	-	0.8215	82.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9754	97.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.74%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.66%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.99%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	91.37%	91.49%
CHEMBL2535	P11166	Glucose transporter	86.98%	98.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.30%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.11%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%

Plants that contains it

• Alangium platanifolium
• Croton penduliflorus
• Galium odoratum
• Gynochthodes officinalis
• Gynochthodes umbellata
• Lychnophora salicifolia
• Neolitsea konishii
• Populus tomentosa
• Rubia tinctorum
• Senna occidentalis
• Vepris louisii

Cross-Links

• PubChem: 11796
• NPASS: NPC120545
• LOTUS: LTS0011911
• wikiData: Q27117163