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

Details

• Internal ID: 102d5780-0aa0-436c-8f7f-3f6948f43e2d
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1S,2R,4R)-4-[(2S,4S,5R,6S)-4-(dimethylamino)-5-[(2S,5S,6R)-5-[(2S,5S,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2,5,7-trihydroxy-6,11-dioxo-2-(2-oxopropyl)-3,4-dihydro-1H-tetracene-1-carboxylate
• SMILES (Canonical): CC1C(CCC(O1)OC2CCC(OC2C)OC3C(OC(CC3N(C)C)OC4CC(C(C5=CC6=C(C(=C45)O)C(=O)C7=C(C6=O)C=CC=C7O)C(=O)OC)(CC(=O)C)O)C)O
• SMILES (Isomeric): C[C@@H]1[C@H](CC[C@@H](O1)O[C@H]2CC[C@@H](O[C@@H]2C)O[C@H]3[C@@H](O[C@@H](C[C@@H]3N(C)C)O[C@@H]4C[C@]([C@H](C5=CC6=C(C(=C45)O)C(=O)C7=C(C6=O)C=CC=C7O)C(=O)OC)(CC(=O)C)O)C)O
• InChI: InChI=1S/C43H55NO15/c1-19(45)17-43(52)18-30(35-24(37(43)42(51)53-7)15-25-36(40(35)50)39(49)34-23(38(25)48)9-8-10-28(34)47)58-33-16-26(44(5)6)41(22(4)56-33)59-32-14-12-29(21(3)55-32)57-31-13-11-27(46)20(2)54-31/h8-10,15,20-22,26-27,29-33,37,41,46-47,50,52H,11-14,16-18H2,1-7H3/t20-,21-,22+,26+,27+,29+,30-,31+,32+,33-,37-,41+,43+/m1/s1
• InChI Key: MLUQAMZHTPPIHO-LJHMSDNNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₅NO₁₅
• Molecular Weight: 825.90 g/mol
• Exact Mass: 825.35717005 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.55
• H-Bond Acceptor: 16
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7388	73.88%
Caco-2	-	0.8637	86.37%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4292	42.92%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.8709	87.09%
OATP1B3 inhibitior	+	0.9163	91.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	+	0.9101	91.01%
P-glycoprotein inhibitior	+	0.7647	76.47%
P-glycoprotein substrate	+	0.8679	86.79%
CYP3A4 substrate	+	0.7427	74.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8288	82.88%
CYP3A4 inhibition	-	0.7717	77.17%
CYP2C9 inhibition	-	0.8624	86.24%
CYP2C19 inhibition	-	0.8693	86.93%
CYP2D6 inhibition	-	0.8295	82.95%
CYP1A2 inhibition	-	0.6216	62.16%
CYP2C8 inhibition	+	0.6189	61.89%
CYP inhibitory promiscuity	-	0.9128	91.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5702	57.02%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9084	90.84%
Skin irritation	-	0.7965	79.65%
Skin corrosion	-	0.9357	93.57%
Ames mutagenesis	+	0.9046	90.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4038	40.38%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.8993	89.93%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7274	72.74%
Acute Oral Toxicity (c)	II	0.4527	45.27%
Estrogen receptor binding	+	0.8681	86.81%
Androgen receptor binding	+	0.8343	83.43%
Thyroid receptor binding	+	0.5473	54.73%
Glucocorticoid receptor binding	+	0.8170	81.70%
Aromatase binding	+	0.7531	75.31%
PPAR gamma	+	0.8146	81.46%
Honey bee toxicity	-	0.6811	68.11%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9143	91.43%

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	99.86%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.32%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	99.29%	96.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.45%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.13%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.60%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.75%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.17%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.02%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	91.79%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.28%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.81%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.30%	96.00%
CHEMBL4208	P20618	Proteasome component C5	87.40%	90.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.29%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.92%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	86.31%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	85.86%	91.49%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.99%	83.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.16%	97.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.97%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.94%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.86%	95.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.75%	94.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.85%	96.67%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.30%	97.14%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.02%	85.11%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.59%	86.67%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139589065
• LOTUS: LTS0144718
• wikiData: Q105167166