Anthrarufin

Details

• Internal ID: 5ed8b22a-51e1-4478-8370-da842930efe5
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1,5-dihydroxyanthracene-9,10-dione
• InChI: InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16H
• InChI Key: JPICKYUTICNNNJ-UHFFFAOYSA-N
• Popularity: 130 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: 3.70
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Anthrarufin
• 117-12-4
• 1,5-dihydroxyanthracene-9,10-dione
• 9,10-Anthracenedione, 1,5-dihydroxy-
• 1,5-Dihydroxyanthrachinon
• 1,5-Dihydroxy-9,10-anthraquinone
• 1,5-Dihydroxy-9,10-anthracenedione
• Anthraquinone, 1,5-dihydroxy-
• CHEBI:37501
• KPB60W5S3M
• NSC-7211
• NSC-646570
• DTXSID8051594
• RefChem:113075
• 1,5-DHAQ
• DTXCID90818191
• 204-175-6
• 1,5-Dihydroxy-anthraquinone
• Az-U
• MFCD00001210
• NSC7211
• 1,5-Dihydroxyanthraquinone, tech.
• 1,5-Dihydroxyanthra-9,10-quinone
• NSC646570
• CCRIS 3150
• 1,5-Dihydroxyanthrachinon [Czech]
• EINECS 204-175-6
• UNII-KPB60W5S3M
• BRN 1881718
• 9, 1,5-dihydroxy-
• ANTHRARUFIN [MI]
• Anthraquinone,5-dihydroxy-
• Epitope ID:116190
• 4-08-00-03268 (Beilstein Handbook Reference)
• CHEMBL55761
• SCHEMBL187843
• SCHEMBL29363946
• SCHEMBL29874705
• CTK8B4089
• 5,9-dihydroxy-1,10-anthraquinone
• 9,10-dihydroxy-1,5-anthraquinone
• Anthrarufin, technical grade, 85%
• BBL013162
• BDBM50568423
• SBB057341
• STK803592
• WLN: L C666 BV IVJ DQ KQ
• AKOS001583186
• 1,10-Anthraquinone, 1,5-dihydroxy-
• 1,5-Dihydroxyanthra-9,10-quinone #
• FD40719
• AS-15880
• NCI60_041483
• SY017889
• D0562
• NS00014594
• ST50455848
• F71867
• AE-641/00185061
• F242816
• 1,5-dihydroxy-9,10-dihydroanthracene-9,10-dione
• Q27117170
• InChI=1/C14H8O4/c15-9-5-1-3-7-11(9)14(18)8-4-2-6-10(16)12(8)13(7)17/h1-6,15-16

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	-	0.6321	63.21%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8545	85.45%
OATP2B1 inhibitior	-	0.7128	71.28%
OATP1B1 inhibitior	+	0.9617	96.17%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8531	85.31%
P-glycoprotein inhibitior	-	0.9362	93.62%
P-glycoprotein substrate	-	0.9834	98.34%
CYP3A4 substrate	-	0.7113	71.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.8357	83.57%
CYP2C9 inhibition	+	0.7750	77.50%
CYP2C19 inhibition	-	0.6159	61.59%
CYP2D6 inhibition	-	0.7456	74.56%
CYP1A2 inhibition	+	0.8918	89.18%
CYP2C8 inhibition	-	0.9773	97.73%
CYP inhibitory promiscuity	-	0.7605	76.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7609	76.09%
Carcinogenicity (trinary)	Warning	0.5038	50.38%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.9831	98.31%
Skin irritation	+	0.7507	75.07%
Skin corrosion	-	0.9842	98.42%
Ames mutagenesis	+	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9092	90.92%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.9500	95.00%
skin sensitisation	-	0.7890	78.90%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.7222	72.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.7905	79.05%
Acute Oral Toxicity (c)	III	0.5401	54.01%
Estrogen receptor binding	+	0.7923	79.23%
Androgen receptor binding	-	0.7588	75.88%
Thyroid receptor binding	-	0.5456	54.56%
Glucocorticoid receptor binding	+	0.8801	88.01%
Aromatase binding	+	0.6607	66.07%
PPAR gamma	+	0.8188	81.88%
Honey bee toxicity	-	0.9486	94.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9793	97.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.93%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.20%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.92%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.77%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.22%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.14%	93.03%
CHEMBL3401	O75469	Pregnane X receptor	83.31%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.32%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.25%	96.67%

Plants that contains it

• Reynoutria japonica

Cross-Links

• PubChem: 8328
• NPASS: NPC375356
• LOTUS: LTS0130567
• wikiData: Q27117170