methyl (1R,2S,4R)-4-[(2S,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate

Details

• Internal ID: 7309ddb4-c2e4-4325-ba4e-77ad18151306
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: methyl (1R,2S,4R)-4-[(2S,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,12-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• SMILES (Canonical): CCC1(CC(C2=C(C1C(=O)OC)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)O)N(C)C)O
• SMILES (Isomeric): CC[C@@]1(C[C@H](C2=C([C@H]1C(=O)OC)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)O[C@@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N(C)C)O
• InChI: InChI=1S/C30H35NO11/c1-6-30(39)11-16(42-17-10-14(31(3)4)24(33)12(2)41-17)19-20(23(30)29(38)40-5)28(37)21-22(27(19)36)26(35)18-13(25(21)34)8-7-9-15(18)32/h7-9,12,14,16-17,23-24,32-33,36-37,39H,6,10-11H2,1-5H3/t12-,14-,16+,17+,23-,24+,30-/m0/s1
• InChI Key: CVACSAHKWDLUII-BXTJAPIWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₅NO₁₁
• Molecular Weight: 585.60 g/mol
• Exact Mass: 585.22101093 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8956	89.56%
Caco-2	-	0.8176	81.76%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.3561	35.61%
OATP2B1 inhibitior	-	0.5912	59.12%
OATP1B1 inhibitior	+	0.9301	93.01%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.8618	86.18%
P-glycoprotein inhibitior	+	0.6469	64.69%
P-glycoprotein substrate	+	0.8627	86.27%
CYP3A4 substrate	+	0.7141	71.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8239	82.39%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8326	83.26%
CYP2C19 inhibition	-	0.8518	85.18%
CYP2D6 inhibition	-	0.8497	84.97%
CYP1A2 inhibition	+	0.5329	53.29%
CYP2C8 inhibition	-	0.7412	74.12%
CYP inhibitory promiscuity	-	0.8559	85.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5984	59.84%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9138	91.38%
Skin irritation	-	0.8066	80.66%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	+	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5867	58.67%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.6801	68.01%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7232	72.32%
Acute Oral Toxicity (c)	II	0.4884	48.84%
Estrogen receptor binding	+	0.8538	85.38%
Androgen receptor binding	+	0.7595	75.95%
Thyroid receptor binding	+	0.5600	56.00%
Glucocorticoid receptor binding	+	0.8508	85.08%
Aromatase binding	+	0.7647	76.47%
PPAR gamma	+	0.8037	80.37%
Honey bee toxicity	-	0.7499	74.99%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9302	93.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.00%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.81%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.89%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.62%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.13%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.27%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.09%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.02%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.12%	93.03%
CHEMBL340	P08684	Cytochrome P450 3A4	87.44%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	86.67%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.40%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.05%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.87%	96.21%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.26%	97.50%
CHEMBL4208	P20618	Proteasome component C5	82.14%	90.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.08%	96.37%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.77%	96.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.71%	85.11%

Plants that contains it

• Cineraria aspera
• Cineraria dieterlenii
• Cineraria parvifolia

Cross-Links

• PubChem: 139589243
• LOTUS: LTS0264707
• wikiData: Q105152246