3-(hydroxymethyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione

Details

• Internal ID: 49de9318-0257-4432-b6ae-aa6200c5b9ac
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 3-(hydroxymethyl)-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• SMILES (Canonical): C1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4OC5C(C(C(C(O5)CO)O)O)O)CO
• SMILES (Isomeric): C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)CO
• InChI: InChI=1S/C27H30O15/c28-6-9-4-11-17(13(5-9)40-27-25(38)23(36)20(33)15(8-30)42-27)21(34)16-10(18(11)31)2-1-3-12(16)39-26-24(37)22(35)19(32)14(7-29)41-26/h1-5,14-15,19-20,22-30,32-33,35-38H,6-8H2/t14-,15-,19-,20+,22+,23+,24-,25-,26-,27-/m1/s1
• InChI Key: QMABOQTWWJKODW-BPUMTERLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -3.69
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7525	75.25%
Caco-2	-	0.9175	91.75%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4625	46.25%
OATP2B1 inhibitior	-	0.7061	70.61%
OATP1B1 inhibitior	+	0.8765	87.65%
OATP1B3 inhibitior	+	0.9697	96.97%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.5154	51.54%
P-glycoprotein inhibitior	-	0.4392	43.92%
P-glycoprotein substrate	-	0.8527	85.27%
CYP3A4 substrate	+	0.6022	60.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8279	82.79%
CYP3A4 inhibition	-	0.9362	93.62%
CYP2C9 inhibition	-	0.9277	92.77%
CYP2C19 inhibition	-	0.8827	88.27%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.9312	93.12%
CYP2C8 inhibition	-	0.6255	62.55%
CYP inhibitory promiscuity	-	0.9071	90.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6892	68.92%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8818	88.18%
Skin irritation	-	0.8481	84.81%
Skin corrosion	-	0.9658	96.58%
Ames mutagenesis	+	0.7136	71.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.7205	72.05%
Micronuclear	+	0.5933	59.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8938	89.38%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.6542	65.42%
Acute Oral Toxicity (c)	IV	0.4657	46.57%
Estrogen receptor binding	+	0.7023	70.23%
Androgen receptor binding	-	0.5448	54.48%
Thyroid receptor binding	-	0.5997	59.97%
Glucocorticoid receptor binding	-	0.6140	61.40%
Aromatase binding	-	0.5348	53.48%
PPAR gamma	+	0.6690	66.90%
Honey bee toxicity	-	0.7450	74.50%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8134	81.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.06%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	94.83%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.73%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.90%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.85%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.19%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.13%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.47%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.38%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.50%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.33%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.59%	99.17%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.91%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.90%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.30%	95.83%

Plants that contains it

• Rheum palmatum

Cross-Links

• PubChem: 11972356
• NPASS: NPC187443