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

Details

• Internal ID: 8315db0c-4643-489a-aaba-5b58f23491c4
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-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(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7C(=CC(=O)C(O7)C)N)O)N(C)C)O
• SMILES (Isomeric): CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)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)N)O)N(C)C)O
• InChI: InChI=1S/C42H52N2O15/c1-8-42(52)16-28(32-21(34(42)40(51)53-7)12-22-33(37(32)50)36(49)31-20(35(22)48)10-9-11-25(31)45)57-29-14-24(44(5)6)38(18(3)54-29)58-30-15-27(47)39(19(4)55-30)59-41-23(43)13-26(46)17(2)56-41/h9-13,17-19,24,27-30,34,38-39,41,45,47,50,52H,8,14-16,43H2,1-7H3/t17-,18-,19-,24-,27-,28-,29-,30-,34-,38+,39+,41-,42+/m0/s1
• InChI Key: OHMUKIWRHXAZQS-SILSRJLASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₂N₂O₁₅
• Molecular Weight: 824.90 g/mol
• Exact Mass: 824.33676896 g/mol
• Topological Polar Surface Area (TPSA): 243.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.22
• 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	+	0.8670	86.70%
Caco-2	-	0.8659	86.59%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4845	48.45%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7845	78.45%
P-glycoprotein inhibitior	+	0.7558	75.58%
P-glycoprotein substrate	+	0.8828	88.28%
CYP3A4 substrate	+	0.7411	74.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.7523	75.23%
CYP2C9 inhibition	-	0.8328	83.28%
CYP2C19 inhibition	-	0.8081	80.81%
CYP2D6 inhibition	-	0.8239	82.39%
CYP1A2 inhibition	-	0.6586	65.86%
CYP2C8 inhibition	+	0.5603	56.03%
CYP inhibitory promiscuity	-	0.7626	76.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4999	49.99%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.7819	78.19%
Skin corrosion	-	0.9243	92.43%
Ames mutagenesis	+	0.9500	95.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4846	48.46%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.7158	71.58%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	+	0.9444	94.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8011	80.11%
Acute Oral Toxicity (c)	III	0.4769	47.69%
Estrogen receptor binding	+	0.8681	86.81%
Androgen receptor binding	+	0.8376	83.76%
Thyroid receptor binding	+	0.5757	57.57%
Glucocorticoid receptor binding	+	0.8663	86.63%
Aromatase binding	+	0.8143	81.43%
PPAR gamma	+	0.8193	81.93%
Honey bee toxicity	-	0.6571	65.71%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9530	95.30%

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	99.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.00%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.83%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	98.72%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.19%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.51%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.92%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.54%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.91%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.07%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.51%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	91.22%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.00%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.16%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.05%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.69%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.21%	100.00%
CHEMBL4208	P20618	Proteasome component C5	87.11%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	85.93%	94.73%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.83%	96.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.83%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.77%	92.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.75%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.64%	96.95%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	82.94%	94.42%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.70%	96.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.37%	92.88%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.19%	99.15%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.05%	83.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.01%	95.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.00%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	80.40%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101697007
• LOTUS: LTS0049084
• wikiData: Q105192152