[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[(9S)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9H-anthracen-9-yl]oxan-2-yl]methyl acetate

Details

• Internal ID: 823b0f09-7545-4b24-9f1f-6ebd51b0f042
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: [(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[(9S)-1,4,5-trihydroxy-7-(hydroxymethyl)-10-oxo-9H-anthracen-9-yl]oxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)C2C3=C(C(=CC(=C3)CO)O)C(=O)C4=C(C=CC(=C24)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)[C@H]2C3=C(C(=CC(=C3)CO)O)C(=O)C4=C(C=CC(=C24)O)O)O)O)O
• InChI: InChI=1S/C23H24O11/c1-8(25)33-7-14-19(29)21(31)22(32)23(34-14)16-10-4-9(6-24)5-13(28)15(10)20(30)18-12(27)3-2-11(26)17(16)18/h2-5,14,16,19,21-24,26-29,31-32H,6-7H2,1H3/t14-,16+,19-,21+,22-,23+/m1/s1
• InChI Key: YNTRKVVINRSNHR-STDMTGHSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₁
• Molecular Weight: 476.40 g/mol
• Exact Mass: 476.13186158 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.61
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5607	56.07%
Caco-2	-	0.9139	91.39%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5996	59.96%
OATP2B1 inhibitior	-	0.5567	55.67%
OATP1B1 inhibitior	-	0.3207	32.07%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.4860	48.60%
P-glycoprotein inhibitior	-	0.5676	56.76%
P-glycoprotein substrate	-	0.8065	80.65%
CYP3A4 substrate	+	0.6141	61.41%
CYP2C9 substrate	+	0.6048	60.48%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.9564	95.64%
CYP2C9 inhibition	-	0.8959	89.59%
CYP2C19 inhibition	-	0.8880	88.80%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	-	0.8204	82.04%
CYP2C8 inhibition	-	0.6055	60.55%
CYP inhibitory promiscuity	-	0.8017	80.17%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7120	71.20%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8618	86.18%
Skin irritation	-	0.8349	83.49%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	+	0.7899	78.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.5291	52.91%
Micronuclear	+	0.5333	53.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9305	93.05%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6199	61.99%
Acute Oral Toxicity (c)	III	0.5347	53.47%
Estrogen receptor binding	+	0.7522	75.22%
Androgen receptor binding	+	0.6545	65.45%
Thyroid receptor binding	-	0.5908	59.08%
Glucocorticoid receptor binding	+	0.6401	64.01%
Aromatase binding	-	0.5551	55.51%
PPAR gamma	+	0.6475	64.75%
Honey bee toxicity	-	0.8480	84.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9341	93.41%

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	98.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.12%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.47%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.18%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.78%	94.73%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.77%	96.38%
CHEMBL4040	P28482	MAP kinase ERK2	89.67%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	89.36%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.14%	97.25%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.93%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.58%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.25%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.16%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.61%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.18%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.60%	89.67%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.96%	96.90%

Plants that contains it

• Aloe marlothii

Cross-Links

• PubChem: 163191305
• LOTUS: LTS0174622
• wikiData: Q105351106