Gaboroquinone A

Details

• Internal ID: 22f42e76-b473-45b2-ad4d-5fe27fe504ed
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-(3-acetyl-4,6-dihydroxy-2-methoxyphenyl)-4,5-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• SMILES (Canonical): CC(=O)C1=C(C=C(C(=C1OC)C2=C3C(=C(C=C2CO)O)C(=O)C4=C(C3=O)C=CC=C4O)O)O
• SMILES (Isomeric): CC(=O)C1=C(C=C(C(=C1OC)C2=C3C(=C(C=C2CO)O)C(=O)C4=C(C3=O)C=CC=C4O)O)O
• InChI: InChI=1S/C24H18O9/c1-9(26)16-14(29)7-15(30)20(24(16)33-2)17-10(8-25)6-13(28)19-21(17)22(31)11-4-3-5-12(27)18(11)23(19)32/h3-7,25,27-30H,8H2,1-2H3
• InChI Key: KUDYATBIEOTCGT-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₁₈O₉
• Molecular Weight: 450.40 g/mol
• Exact Mass: 450.09508215 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.65
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• CHEBI:65940
• 1-(3-acetyl-4,6-dihydroxy-2-methoxyphenyl)-4,5-dihydroxy-2-(hydroxymethyl)anthracene-9,10-dione
• CHEMBL483822
• SCHEMBL9980698
• Q27134440

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9615	96.15%
Caco-2	-	0.7713	77.13%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8403	84.03%
OATP2B1 inhibitior	+	0.5727	57.27%
OATP1B1 inhibitior	+	0.9046	90.46%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4592	45.92%
P-glycoprotein inhibitior	-	0.6313	63.13%
P-glycoprotein substrate	-	0.6656	66.56%
CYP3A4 substrate	+	0.5871	58.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8189	81.89%
CYP3A4 inhibition	-	0.5988	59.88%
CYP2C9 inhibition	+	0.6538	65.38%
CYP2C19 inhibition	+	0.5491	54.91%
CYP2D6 inhibition	-	0.7924	79.24%
CYP1A2 inhibition	+	0.8052	80.52%
CYP2C8 inhibition	-	0.5852	58.52%
CYP inhibitory promiscuity	+	0.7366	73.66%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8575	85.75%
Carcinogenicity (trinary)	Non-required	0.7273	72.73%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.5675	56.75%
Skin irritation	-	0.7836	78.36%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.7577	75.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.3870	38.70%
Micronuclear	+	0.6659	66.59%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.9123	91.23%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5403	54.03%
Acute Oral Toxicity (c)	III	0.5759	57.59%
Estrogen receptor binding	+	0.8431	84.31%
Androgen receptor binding	+	0.5589	55.89%
Thyroid receptor binding	-	0.6902	69.02%
Glucocorticoid receptor binding	+	0.7406	74.06%
Aromatase binding	-	0.6253	62.53%
PPAR gamma	+	0.7280	72.80%
Honey bee toxicity	-	0.8727	87.27%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9656	96.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.15%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.85%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.17%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.13%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.96%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL2535	P11166	Glucose transporter	89.57%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.86%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.63%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.59%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.73%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.33%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.26%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	84.27%	90.20%
CHEMBL1937	Q92769	Histone deacetylase 2	84.02%	94.75%
CHEMBL340	P08684	Cytochrome P450 3A4	84.01%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.73%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.00%	96.95%
CHEMBL4208	P20618	Proteasome component C5	81.07%	90.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.13%	96.67%

Plants that contains it

• Bulbine frutescens

Cross-Links

• PubChem: 10072444
• LOTUS: LTS0268931
• wikiData: Q27134440