1,3-Dihydroxyanthraquinone

Details

• Internal ID: e72b7525-f77f-4529-b7a5-c24bf16c403b
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,3-dihydroxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=CC(=C3)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=CC(=C3)O)O
• InChI: InChI=1S/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16H
• InChI Key: WPWWKBNOXTZDQJ-UHFFFAOYSA-N
• Popularity: 95 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: 3.20
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 1,3-Dihydroxyanthraquinone
• 518-83-2
• Purpuro
• Purpuroxathin
• Purpuroxathine
• Xanthopurpin
• 1,3-dihydroxyanthracene-9,10-dione
• Purpuroxanthin
• 1,3-Dihydroxy-9,10-anthracenedione
• 1,3-dihydroxy-9,10-anthraquinone
• CCRIS 3523
• Anthraquinone, 1,3-dihydroxy-
• 9,10-Anthracenedione, 1,3-dihydroxy-
• UNII-9RBB2G1GQB
• 9RBB2G1GQB
• BRN 1979394
• XANTHOPURPURINE
• CHEBI:37502
• C.I. 75340
• 1,3-Dihydroxy-Anthraquinone
• 4-08-00-03259 (Beilstein Handbook Reference)
• 9,10-Anthracenedione, 1,3-dihydroxy- (9CI)
• 1,3-DIHYDROXY-9,10-DIHYDROANTHRACENE-9,10-DIONE
• Purpuro (Ligand 1)
• CHEMBL372711
• SCHEMBL1426707
• DTXSID6075431
• WPWWKBNOXTZDQJ-UHFFFAOYSA-N
• HY-N7619
• BDBM50400183
• AKOS015963955
• LS-20668
• MS-23397
• 1,3-Dihydroxy-9,10-anthracenedione, 9CI
• CS-0134802
• Q4545678
• InChI=1/C14H8O4/c15-7-5-10-12(11(16)6-7)14(18)9-4-2-1-3-8(9)13(10)17/h1-6,15-16

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9804	98.04%
Caco-2	+	0.5447	54.47%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7686	76.86%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.9513	95.13%
OATP1B3 inhibitior	+	0.9029	90.29%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8967	89.67%
P-glycoprotein inhibitior	-	0.9504	95.04%
P-glycoprotein substrate	-	0.9854	98.54%
CYP3A4 substrate	-	0.6410	64.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.5609	56.09%
CYP2C9 inhibition	+	0.7909	79.09%
CYP2C19 inhibition	+	0.5138	51.38%
CYP2D6 inhibition	-	0.6834	68.34%
CYP1A2 inhibition	+	0.8742	87.42%
CYP2C8 inhibition	-	0.8544	85.44%
CYP inhibitory promiscuity	-	0.6363	63.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8096	80.96%
Carcinogenicity (trinary)	Non-required	0.5839	58.39%
Eye corrosion	-	0.9923	99.23%
Eye irritation	+	0.9813	98.13%
Skin irritation	+	0.7224	72.24%
Skin corrosion	-	0.9604	96.04%
Ames mutagenesis	+	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8382	83.82%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.7802	78.02%
skin sensitisation	-	0.7151	71.51%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.7414	74.14%
Acute Oral Toxicity (c)	III	0.6800	68.00%
Estrogen receptor binding	+	0.8431	84.31%
Androgen receptor binding	+	0.7711	77.11%
Thyroid receptor binding	+	0.5279	52.79%
Glucocorticoid receptor binding	+	0.8724	87.24%
Aromatase binding	+	0.7533	75.33%
PPAR gamma	+	0.7494	74.94%
Honey bee toxicity	-	0.8470	84.70%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9730	97.30%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	1700 nM	Ki	PMID: 23167494
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	2270 nM	Ki	PMID: 23167494

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.63%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.41%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.05%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.21%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.96%	99.15%
CHEMBL1929	P47989	Xanthine dehydrogenase	90.89%	96.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.73%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.16%	89.00%
CHEMBL2535	P11166	Glucose transporter	86.39%	98.75%
CHEMBL4208	P20618	Proteasome component C5	85.89%	90.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.46%	82.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.31%	96.67%
CHEMBL3401	O75469	Pregnane X receptor	81.75%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.43%	93.40%

Plants that contains it

• Alangium platanifolium
• Croton penduliflorus
• Galium odoratum
• Galium spurium
• Gynochthodes umbellata
• Ipomoea cairica
• Knoxia roxburghii
• Lychnophora salicifolia
• Neolitsea konishii
• Populus tomentosa
• Rubia argyi
• Rubia cordifolia
• Rubia oncotricha
• Rubia tinctorum
• Rubia wallichiana
• Rubia yunnanensis
• Vepris louisii

Cross-Links

• PubChem: 196978
• NPASS: NPC44437
• ChEMBL: CHEMBL372711
• LOTUS: LTS0085424
• wikiData: Q4545678