methyl (1R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

Details

• Internal ID: b2bf098b-e643-4442-8100-622021e87a8c
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[[(2R,6S)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• SMILES (Canonical): CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7C=CC(=O)C(O7)C)O)N(C)C)O
• SMILES (Isomeric): CCC1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@@H]([C@@H](O6)C)O[C@H]7C=CC(=O)[C@@H](O7)C)O)N(C)C)O
• InChI: InChI=1S/C42H51NO16/c1-8-42(52)16-27(31-20(35(42)41(51)53-7)13-21-32(37(31)49)38(50)34-25(46)10-9-24(45)33(34)36(21)48)57-29-14-22(43(5)6)39(18(3)55-29)59-30-15-26(47)40(19(4)56-30)58-28-12-11-23(44)17(2)54-28/h9-13,17-19,22,26-30,35,39-40,45-47,49,52H,8,14-16H2,1-7H3/t17-,18-,19-,22-,26-,27-,28-,29-,30-,35-,39+,40+,42?/m0/s1
• InChI Key: QEAUOZOEMLMFLN-XDUZAUHZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₁NO₁₆
• Molecular Weight: 825.80 g/mol
• Exact Mass: 825.32078454 g/mol
• Topological Polar Surface Area (TPSA): 237.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8820	88.20%
Caco-2	-	0.8679	86.79%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.3945	39.45%
OATP2B1 inhibitior	-	0.7165	71.65%
OATP1B1 inhibitior	+	0.8752	87.52%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7629	76.29%
P-glycoprotein inhibitior	+	0.7513	75.13%
P-glycoprotein substrate	+	0.8513	85.13%
CYP3A4 substrate	+	0.7298	72.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8678	86.78%
CYP3A4 inhibition	-	0.7711	77.11%
CYP2C9 inhibition	-	0.8449	84.49%
CYP2C19 inhibition	-	0.8289	82.89%
CYP2D6 inhibition	-	0.8128	81.28%
CYP1A2 inhibition	-	0.5730	57.30%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.7974	79.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5063	50.63%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9093	90.93%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	+	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4800	48.00%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8012	80.12%
Acute Oral Toxicity (c)	II	0.4503	45.03%
Estrogen receptor binding	+	0.8701	87.01%
Androgen receptor binding	+	0.8168	81.68%
Thyroid receptor binding	+	0.5505	55.05%
Glucocorticoid receptor binding	+	0.8650	86.50%
Aromatase binding	+	0.8190	81.90%
PPAR gamma	+	0.8173	81.73%
Honey bee toxicity	-	0.6898	68.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9566	95.66%

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	99.84%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.77%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.73%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.08%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	96.07%	96.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.74%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.86%	97.09%
CHEMBL4208	P20618	Proteasome component C5	92.28%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.25%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.48%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.29%	96.21%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.03%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.49%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	86.95%	91.19%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.93%	95.64%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.74%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.68%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	86.63%	95.93%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.04%	85.11%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.76%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.11%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.64%	97.25%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.64%	96.67%
CHEMBL3401	O75469	Pregnane X receptor	84.39%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.70%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.45%	91.07%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.13%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.77%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.02%	96.90%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 24840376
• LOTUS: LTS0268180
• wikiData: Q104401995