1-Hydroxyanthraquinone

Details

• Internal ID: b3cc6bbe-a7bc-48f5-9d31-f4a7ac4a2483
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O
• InChI: InChI=1S/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7,15H
• InChI Key: BTLXPCBPYBNQNR-UHFFFAOYSA-N
• Popularity: 653 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: 3.50
• Atomic LogP (AlogP): 2.17
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 129-43-1
• 1-hydroxyanthracene-9,10-dione
• 1-Hydroxy anthraquinone
• 1-Hydroxy-9,10-anthraquinone
• 1-Hydroxyanthrachinon
• 9,10-Anthracenedione, 1-hydroxy-
• Anthraquinone, 1-hydroxy-
• Hydroxyanthraquinone
• 1-Hydroxyanthra-9,10-quinone
• alpha-Hydroxyanthraquinone
• 1-Hydroxyanthrachinon [Czech]
• CCRIS 3694
• CHEBI:28877
• HSDB 7145
• 1-hydroxy-anthraquinone
• NSC 8640
• EINECS 204-946-7
• UNII-LFU129OE9H
• .alpha.-Hydroxyanthraquinone
• BRN 1912751
• LFU129OE9H
• NSC-8640
• MFCD00058946
• 1-hydroxy-9,10-anthracenedione
• 4-hydroxyanthraquinone
• 9, 1-hydroxy-
• Hydroxyanthraquinone, 1-
• ERYTHROXYANTHRAQUINONE
• CBDivE_013840
• SCHEMBL145303
• 9-hydroxy-1,10-anthraquinone
• CHEMBL501834
• DTXSID1020722
• NSC8640
• 1-hydroxy-anthracene-9,10-dione
• 1-Hydroxyanthra-9,10-quinone #
• WLN: L C666 BV IVJ DQ
• BDBM50025501
• 1-HYDROXYANTHRAQUINONE [HSDB]
• 1-HYDROXYANTHRAQUINONE [IARC]
• AKOS015856426
• CS-W000838
• GS-3366
• HY-W000838
• LS-7444
• PD133665
• SY052323
• 1-Hydroxyanthra-9,10-quinone, AldrichCPR
• FT-0730299
• H0354
• 1-hydroxy-9,10-dihydroanthracene-9,10-dione
• C02980
• O10414
• A805939
• W-108363
• 1-hydroxyanthracene-9,10-dione;1-hydroxyanthraquinone
• Q27103937
• InChI=1/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)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	+	0.6556	65.56%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8429	84.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9622	96.22%
OATP1B3 inhibitior	+	0.9712	97.12%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8573	85.73%
P-glycoprotein inhibitior	-	0.9374	93.74%
P-glycoprotein substrate	-	0.9780	97.80%
CYP3A4 substrate	-	0.6815	68.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.9408	94.08%
CYP2C9 inhibition	-	0.5514	55.14%
CYP2C19 inhibition	-	0.6779	67.79%
CYP2D6 inhibition	-	0.8045	80.45%
CYP1A2 inhibition	+	0.9387	93.87%
CYP2C8 inhibition	-	0.9708	97.08%
CYP inhibitory promiscuity	-	0.8457	84.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7509	75.09%
Carcinogenicity (trinary)	Warning	0.5482	54.82%
Eye corrosion	-	0.9796	97.96%
Eye irritation	+	0.9622	96.22%
Skin irritation	+	0.8045	80.45%
Skin corrosion	-	0.9904	99.04%
Ames mutagenesis	+	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9036	90.36%
Micronuclear	+	0.5749	57.49%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.6048	60.48%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.7444	74.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.7692	76.92%
Acute Oral Toxicity (c)	III	0.4672	46.72%
Estrogen receptor binding	+	0.8014	80.14%
Androgen receptor binding	-	0.5287	52.87%
Thyroid receptor binding	+	0.5538	55.38%
Glucocorticoid receptor binding	+	0.7726	77.26%
Aromatase binding	+	0.7205	72.05%
PPAR gamma	+	0.7821	78.21%
Honey bee toxicity	-	0.8783	87.83%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9712	97.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.71%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.83%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.64%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.04%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.59%	99.15%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.80%	82.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.53%	96.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.48%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	84.06%	94.73%
CHEMBL2535	P11166	Glucose transporter	83.65%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.06%	89.00%

Plants that contains it

• Angelica decursiva
• Gynochthodes officinalis
• Handroanthus impetiginosus
• Morinda citrifolia
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Senna occidentalis

Cross-Links

• PubChem: 8512
• NPASS: NPC300274
• LOTUS: LTS0273108
• wikiData: Q27103937