(3R)-3,8-dihydroxy-9-[4-hydroxy-6-methyl-5-[6-methyl-5-[(6-methyl-5-oxo-2H-pyran-2-yl)oxy]oxan-2-yl]oxyoxan-2-yl]-5-methoxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

Details

• Internal ID: 5f720184-9d8f-4c5c-8678-448f53ce42b8
• Taxonomy: Phenylpropanoids and polyketides > Angucyclines
• IUPAC Name: (3R)-3,8-dihydroxy-9-[4-hydroxy-6-methyl-5-[6-methyl-5-[(6-methyl-5-oxo-2H-pyran-2-yl)oxy]oxan-2-yl]oxyoxan-2-yl]-5-methoxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
• SMILES (Canonical): CC1C(CCC(O1)OC2C(OC(CC2O)C3=C(C4=C(C=C3)C(=O)C5=C6C(=C(C=C5C4=O)OC)CC(CC6=O)(C)O)O)C)OC7C=CC(=O)C(O7)C
• SMILES (Isomeric): CC1C(CCC(O1)OC2C(OC(CC2O)C3=C(C4=C(C=C3)C(=O)C5=C6C(=C(C=C5C4=O)OC)C[C@@](CC6=O)(C)O)O)C)OC7C=CC(=O)C(O7)C
• InChI: InChI=1S/C38H42O13/c1-16-23(39)8-10-29(48-16)50-26-9-11-30(49-17(26)2)51-37-18(3)47-28(13-24(37)40)19-6-7-20-33(34(19)42)36(44)21-12-27(46-5)22-14-38(4,45)15-25(41)31(22)32(21)35(20)43/h6-8,10,12,16-18,24,26,28-30,37,40,42,45H,9,11,13-15H2,1-5H3/t16?,17?,18?,24?,26?,28?,29?,30?,37?,38-/m1/s1
• InChI Key: RJSDJAHVRVFSLU-ZGIZWTHSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₂O₁₃
• Molecular Weight: 706.70 g/mol
• Exact Mass: 706.26254139 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9371	93.71%
Caco-2	-	0.8546	85.46%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7082	70.82%
OATP2B1 inhibitior	-	0.5673	56.73%
OATP1B1 inhibitior	+	0.8366	83.66%
OATP1B3 inhibitior	+	0.8768	87.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9483	94.83%
P-glycoprotein inhibitior	+	0.7683	76.83%
P-glycoprotein substrate	+	0.7836	78.36%
CYP3A4 substrate	+	0.7411	74.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.8144	81.44%
CYP2C9 inhibition	-	0.9360	93.60%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.7217	72.17%
CYP2C8 inhibition	+	0.6723	67.23%
CYP inhibitory promiscuity	-	0.9286	92.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5034	50.34%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9172	91.72%
Skin irritation	-	0.7225	72.25%
Skin corrosion	-	0.9297	92.97%
Ames mutagenesis	+	0.6030	60.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.4109	41.09%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.8963	89.63%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4912	49.12%
Acute Oral Toxicity (c)	I	0.4928	49.28%
Estrogen receptor binding	+	0.8758	87.58%
Androgen receptor binding	+	0.7093	70.93%
Thyroid receptor binding	+	0.5152	51.52%
Glucocorticoid receptor binding	+	0.8165	81.65%
Aromatase binding	+	0.7523	75.23%
PPAR gamma	+	0.7342	73.42%
Honey bee toxicity	-	0.7140	71.40%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5451	54.51%
Fish aquatic toxicity	+	0.9851	98.51%

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	99.80%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.44%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.61%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	96.48%	92.94%
CHEMBL1951	P21397	Monoamine oxidase A	95.73%	91.49%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	95.72%	96.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.43%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.20%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.93%	95.56%
CHEMBL240	Q12809	HERG	94.85%	89.76%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.70%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.59%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.12%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.31%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.28%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.10%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	91.40%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.08%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.94%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.59%	95.93%
CHEMBL1871	P10275	Androgen Receptor	88.99%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.54%	94.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.28%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.11%	91.07%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	87.05%	96.67%
CHEMBL2535	P11166	Glucose transporter	85.41%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.12%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	85.08%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.31%	93.04%
CHEMBL2056	P21728	Dopamine D1 receptor	84.10%	91.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.01%	82.67%
CHEMBL220	P22303	Acetylcholinesterase	83.34%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.70%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.50%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139584948
• LOTUS: LTS0271091
• wikiData: Q77378815