(1S,11R,12R,13R,21S,22S,23R,24S)-13-(4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl)oxy-23-(dimethylamino)-11,15,22,24-tetrahydroxy-12-methoxy-1,11-dimethyl-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7(16),8,14-hexaene-6,17-dione

Details

• Internal ID: f8aa3ee2-8739-41ec-a71a-a7437d51c35a
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: (1S,11R,12R,13R,21S,22S,23R,24S)-13-(4,5-dihydroxy-3-methoxy-4,6-dimethyloxan-2-yl)oxy-23-(dimethylamino)-11,15,22,24-tetrahydroxy-12-methoxy-1,11-dimethyl-20,25-dioxahexacyclo[19.3.1.02,19.05,18.07,16.09,14]pentacosa-2(19),3,5(18),7(16),8,14-hexaene-6,17-dione
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC6=C5OC7C(C(C(C6(O7)C)O)N(C)C)O)(C)O)OC)OC)(C)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)O[C@H]2[C@H]([C@](CC3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC6=C5O[C@@H]7[C@H]([C@@H]([C@@H]([C@]6(O7)C)O)N(C)C)O)(C)O)OC)OC)(C)O)O
• InChI: InChI=1S/C36H45NO14/c1-13-28(42)35(3,45)31(47-8)33(48-13)50-27-18-14(12-34(2,44)30(27)46-7)11-16-19(23(18)39)24(40)20-15(22(16)38)9-10-17-26(20)49-32-25(41)21(37(5)6)29(43)36(17,4)51-32/h9-11,13,21,25,27-33,39,41-45H,12H2,1-8H3/t13?,21-,25-,27+,28?,29-,30+,31?,32-,33?,34+,35?,36-/m0/s1
• InChI Key: BZFHXAJTVQBODO-WJQQIYQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₅NO₁₄
• Molecular Weight: 715.70 g/mol
• Exact Mass: 715.28400511 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.04
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7364	73.64%
Caco-2	-	0.8571	85.71%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Lysosomes	0.5198	51.98%
OATP2B1 inhibitior	-	0.7072	70.72%
OATP1B1 inhibitior	+	0.8334	83.34%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7646	76.46%
P-glycoprotein inhibitior	+	0.7258	72.58%
P-glycoprotein substrate	+	0.8282	82.82%
CYP3A4 substrate	+	0.7335	73.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	-	0.7907	79.07%
CYP2C9 inhibition	-	0.9059	90.59%
CYP2C19 inhibition	-	0.9040	90.40%
CYP2D6 inhibition	-	0.5558	55.58%
CYP1A2 inhibition	+	0.8229	82.29%
CYP2C8 inhibition	+	0.6600	66.00%
CYP inhibitory promiscuity	-	0.9086	90.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4791	47.91%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.8061	80.61%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	+	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4237	42.37%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	-	0.8834	88.34%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7213	72.13%
Acute Oral Toxicity (c)	III	0.7258	72.58%
Estrogen receptor binding	+	0.7940	79.40%
Androgen receptor binding	+	0.7311	73.11%
Thyroid receptor binding	+	0.5346	53.46%
Glucocorticoid receptor binding	+	0.7406	74.06%
Aromatase binding	+	0.6598	65.98%
PPAR gamma	+	0.7573	75.73%
Honey bee toxicity	-	0.6667	66.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8449	84.49%

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	99.44%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.74%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.81%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.70%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.91%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.60%	86.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	92.34%	85.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.64%	95.64%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.95%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.84%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.77%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.62%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.87%	99.23%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.23%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.54%	97.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.79%	94.42%
CHEMBL4208	P20618	Proteasome component C5	83.75%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	83.57%	94.73%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.51%	91.03%
CHEMBL226	P30542	Adenosine A1 receptor	83.21%	95.93%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.11%	90.24%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.90%	82.38%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.66%	96.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.11%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.87%	96.38%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.56%	80.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.39%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.56%	91.07%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.26%	100.00%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.02%	88.00%

Plants that contains it

• Berberis integerrima

Cross-Links

• PubChem: 139587745
• LOTUS: LTS0123386
• wikiData: Q105240997