methyl (1R,2R)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[[(5S,12S,14S)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]oxy]-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

Details

• Internal ID: 506c377e-47e6-48f6-8fd9-3f6f64703210
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1R,2R)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[[(5S,12S,14S)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]oxy]-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)OC6CC7C(C(O6)C)OC8C(O7)CC(=O)C(O8)C)N(C)C)O
• SMILES (Isomeric): CC[C@]1(CC(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]6CC7C([C@@H](O6)C)OC8C(O7)CC(=O)[C@@H](O8)C)N(C)C)O
• InChI: InChI=1S/C42H51NO15/c1-8-42(50)16-28(32-21(34(42)40(49)51-7)12-22-33(37(32)48)36(47)31-20(35(22)46)10-9-11-24(31)44)56-29-13-23(43(5)6)38(18(3)52-29)57-30-15-26-39(19(4)53-30)58-41-27(55-26)14-25(45)17(2)54-41/h9-12,17-19,23,26-30,34,38-39,41,44,48,50H,8,13-16H2,1-7H3/t17-,18-,19-,23-,26?,27?,28?,29-,30-,34-,38+,39?,41?,42+/m0/s1
• InChI Key: RQHZAASWYUEYCJ-SVYUPZDJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₅₁NO₁₅
• Molecular Weight: 809.80 g/mol
• Exact Mass: 809.32586992 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 16
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8271	82.71%
Caco-2	-	0.8635	86.35%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.4443	44.43%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8697	86.97%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7633	76.33%
P-glycoprotein inhibitior	+	0.7675	76.75%
P-glycoprotein substrate	+	0.8565	85.65%
CYP3A4 substrate	+	0.7455	74.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8487	84.87%
CYP3A4 inhibition	-	0.7738	77.38%
CYP2C9 inhibition	-	0.8613	86.13%
CYP2C19 inhibition	-	0.8510	85.10%
CYP2D6 inhibition	-	0.8152	81.52%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.6463	64.63%
CYP inhibitory promiscuity	-	0.8394	83.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5668	56.68%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.9600	96.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4551	45.51%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.8939	89.39%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.6402	64.02%
Acute Oral Toxicity (c)	II	0.5336	53.36%
Estrogen receptor binding	+	0.8728	87.28%
Androgen receptor binding	+	0.8483	84.83%
Thyroid receptor binding	+	0.5328	53.28%
Glucocorticoid receptor binding	+	0.8611	86.11%
Aromatase binding	+	0.8020	80.20%
PPAR gamma	+	0.8173	81.73%
Honey bee toxicity	-	0.6773	67.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9077	90.77%

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	98.95%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.05%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.79%	96.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.16%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.69%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.43%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.32%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	90.88%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.83%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.34%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	89.89%	95.93%
CHEMBL4208	P20618	Proteasome component C5	87.96%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.69%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.98%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.59%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	83.99%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.34%	99.17%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.64%	85.11%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.47%	96.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.38%	95.64%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.26%	83.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.52%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.35%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.33%	96.95%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.25%	96.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.24%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.20%	90.71%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.07%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162960493
• LOTUS: LTS0245001
• wikiData: Q105243332