methyl (1S,10R,12R,13S,22R,23S,24S)-23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(2S,3S,4R,5R,6R)-3,4,5-trimethoxy-4,6-dimethyloxan-2-yl]oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate

Details

• Internal ID: bbb97807-e5c4-47c0-830e-c3be2d10cc50
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1S,10R,12R,13S,22R,23S,24S)-23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(2S,3S,4R,5R,6R)-3,4,5-trimethoxy-4,6-dimethyloxan-2-yl]oxy-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CC(C(C3=CC4=C(C(=C23)O)C(=O)C5=C(C=C6C(=C5C4=O)OC7C(C(C(C6(O7)C)O)N(C)C)O)O)C(=O)OC)(C)O)OC)(C)OC)OC
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@]([C@@H]([C@H](O1)O[C@@H]2C[C@@]([C@H](C3=CC4=C(C(=C23)O)C(=O)C5=C(C=C6C(=C5C4=O)OC7[C@@H]([C@H]([C@@H]([C@]6(O7)C)O)N(C)C)O)O)C(=O)OC)(C)O)OC)(C)OC)OC
• InChI: InChI=1S/C39H49NO16/c1-14-32(49-7)39(4,52-10)33(50-8)36(53-14)54-19-13-37(2,48)24(34(47)51-9)15-11-16-21(27(43)20(15)19)28(44)22-18(41)12-17-30(23(22)26(16)42)55-35-29(45)25(40(5)6)31(46)38(17,3)56-35/h11-12,14,19,24-25,29,31-33,35-36,41,43,45-46,48H,13H2,1-10H3/t14-,19-,24-,25-,29-,31+,32-,33-,35?,36-,37-,38+,39-/m1/s1
• InChI Key: KGTDRFCXGRULNK-LIKBLWDQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₉NO₁₆
• Molecular Weight: 787.80 g/mol
• Exact Mass: 787.30513448 g/mol
• Topological Polar Surface Area (TPSA): 229.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.14
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5690	56.90%
Caco-2	-	0.8548	85.48%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.5243	52.43%
OATP2B1 inhibitior	-	0.7053	70.53%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6695	66.95%
P-glycoprotein inhibitior	+	0.7378	73.78%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7346	73.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8516	85.16%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.6126	61.26%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7105	71.05%
CYP inhibitory promiscuity	-	0.8662	86.62%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4559	45.59%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9091	90.91%
Skin irritation	-	0.8131	81.31%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	+	0.8072	80.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.4616	46.16%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6092	60.92%
Acute Oral Toxicity (c)	III	0.7658	76.58%
Estrogen receptor binding	+	0.7850	78.50%
Androgen receptor binding	+	0.7685	76.85%
Thyroid receptor binding	+	0.5478	54.78%
Glucocorticoid receptor binding	+	0.8020	80.20%
Aromatase binding	+	0.7189	71.89%
PPAR gamma	+	0.7690	76.90%
Honey bee toxicity	-	0.6507	65.07%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8199	81.99%

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	99.53%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.64%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	96.56%	96.38%
CHEMBL2581	P07339	Cathepsin D	96.22%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.04%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.16%	96.21%
CHEMBL1951	P21397	Monoamine oxidase A	90.60%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.04%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.07%	95.89%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.02%	94.42%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	87.11%	85.11%
CHEMBL3401	O75469	Pregnane X receptor	86.66%	94.73%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.34%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	86.09%	91.19%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	85.92%	82.38%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	85.77%	80.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.51%	100.00%
CHEMBL261	P00915	Carbonic anhydrase I	83.11%	96.76%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.93%	96.77%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.78%	96.90%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.75%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.13%	92.94%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.65%	100.00%
CHEMBL2535	P11166	Glucose transporter	81.07%	98.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.45%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162877197
• LOTUS: LTS0024951
• wikiData: Q105140967