(3R,4aR,12bS)-9-[(4R,5R,6R)-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]-3,4a,8-trihydroxy-12b-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

Details

• Internal ID: afaba0eb-6768-4384-8b9f-417b4e1c8104
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Anthraquinone glycosides
• IUPAC Name: (3R,4aR,12bS)-9-[(4R,5R,6R)-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]-3,4a,8-trihydroxy-12b-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
• SMILES (Canonical): CC1C(CCC(O1)OC23C(=O)CC(CC2(C=CC4=C3C(=O)C5=C(C4=O)C(=C(C=C5)C6CC(C(C(O6)C)O)OC7CCC(C(O7)C)OC8CC(C(C(O8)C)O)O)O)O)(C)O)O
• SMILES (Isomeric): C[C@H]1[C@H](CC[C@@H](O1)O[C@]23C(=O)C[C@](C[C@]2(C=CC4=C3C(=O)C5=C(C4=O)C(=C(C=C5)C6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7CC[C@@H]([C@@H](O7)C)O[C@H]8C[C@H]([C@@H]([C@H](O8)C)O)O)O)O)(C)O)O
• InChI: InChI=1S/C43H56O17/c1-18-25(44)8-10-32(55-18)60-43-30(46)16-41(5,52)17-42(43,53)13-12-24-35(43)40(51)23-7-6-22(38(49)34(23)39(24)50)28-15-29(37(48)21(4)54-28)59-31-11-9-27(19(2)56-31)58-33-14-26(45)36(47)20(3)57-33/h6-7,12-13,18-21,25-29,31-33,36-37,44-45,47-49,52-53H,8-11,14-17H2,1-5H3/t18-,19-,20+,21+,25-,26+,27-,28?,29+,31-,32-,33-,36+,37+,41-,42-,43-/m0/s1
• InChI Key: FJSYXNOFZQFOAN-VHAJQMGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₆O₁₇
• Molecular Weight: 844.90 g/mol
• Exact Mass: 844.35175031 g/mol
• Topological Polar Surface Area (TPSA): 257.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9350	93.50%
Caco-2	-	0.8728	87.28%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7075	70.75%
OATP2B1 inhibitior	-	0.8669	86.69%
OATP1B1 inhibitior	+	0.8514	85.14%
OATP1B3 inhibitior	-	0.2220	22.20%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.9628	96.28%
P-glycoprotein inhibitior	+	0.7359	73.59%
P-glycoprotein substrate	+	0.7598	75.98%
CYP3A4 substrate	+	0.7362	73.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8724	87.24%
CYP3A4 inhibition	-	0.8718	87.18%
CYP2C9 inhibition	-	0.8399	83.99%
CYP2C19 inhibition	-	0.8724	87.24%
CYP2D6 inhibition	-	0.9201	92.01%
CYP1A2 inhibition	-	0.8065	80.65%
CYP2C8 inhibition	+	0.6502	65.02%
CYP inhibitory promiscuity	-	0.9261	92.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5736	57.36%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9091	90.91%
Skin irritation	-	0.6346	63.46%
Skin corrosion	-	0.9189	91.89%
Ames mutagenesis	+	0.5346	53.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6885	68.85%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.5050	50.50%
skin sensitisation	-	0.8448	84.48%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6431	64.31%
Acute Oral Toxicity (c)	II	0.4138	41.38%
Estrogen receptor binding	+	0.8380	83.80%
Androgen receptor binding	+	0.7532	75.32%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.7681	76.81%
Aromatase binding	+	0.6577	65.77%
PPAR gamma	+	0.8051	80.51%
Honey bee toxicity	-	0.7477	74.77%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9905	99.05%

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	99.26%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.75%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.25%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	96.08%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	94.23%	91.49%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.06%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.99%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.27%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.19%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.98%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.35%	85.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.09%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.76%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.73%	96.21%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.61%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.28%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.58%	96.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.95%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.74%	93.04%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.57%	82.67%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.13%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.64%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.01%	97.14%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.36%	95.69%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.90%	96.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.03%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.62%	97.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.36%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.30%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162846168
• LOTUS: LTS0127413
• wikiData: Q104996324