(7S,9R,10S)-7-[(2R,4R,5R,6R)-4-(dimethylamino)-5-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-[(2S,4R,5R,6S)-4-(dimethylamino)-5-[(2S,4R,5R,6R)-4-hydroxy-5-[(2S,5S,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-1,4,6,9,11-pentahydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Details

• Internal ID: fda31c21-bb4e-485f-bfc0-3099dff8b1f0
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: (7S,9R,10S)-7-[(2R,4R,5R,6R)-4-(dimethylamino)-5-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-[(2S,4R,5R,6S)-4-(dimethylamino)-5-[(2S,4R,5R,6R)-4-hydroxy-5-[(2S,5S,6R)-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-9-ethyl-1,4,6,9,11-pentahydroxy-8,10-dihydro-7H-tetracene-5,12-dione
• SMILES (Canonical): CCC1(CC(C2=C(C1OC3CC(C(C(O3)C)OC4CC(C(C(O4)C)OC5CCC(C(O5)C)O)O)N(C)C)C(=C6C(=C2O)C(=O)C7=C(C=CC(=C7C6=O)O)O)O)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1CCC(C(O1)C)O)O)N(C)C)O
• SMILES (Isomeric): CC[C@]1(C[C@@H](C2=C([C@@H]1O[C@H]3C[C@H]([C@H]([C@@H](O3)C)O[C@H]4C[C@H]([C@H]([C@H](O4)C)O[C@H]5CC[C@@H]([C@H](O5)C)O)O)N(C)C)C(=C6C(=C2O)C(=O)C7=C(C=CC(=C7C6=O)O)O)O)O[C@H]8C[C@H]([C@H]([C@H](O8)C)O[C@@H]9C[C@@H]([C@@H]([C@@H](O9)C)O[C@H]1CC[C@@H]([C@@H](O1)C)O)O)N(C)C)O
• InChI: InChI=1S/C60H88N2O23/c1-12-60(73)23-38(80-41-19-30(61(8)9)55(26(4)76-41)83-43-21-36(67)57(28(6)78-43)81-39-17-15-32(63)24(2)74-39)47-50(54(72)49-48(53(47)71)51(69)45-34(65)13-14-35(66)46(45)52(49)70)59(60)85-42-20-31(62(10)11)56(27(5)77-42)84-44-22-37(68)58(29(7)79-44)82-40-18-16-33(64)25(3)75-40/h13-14,24-33,36-44,55-59,63-68,71-73H,12,15-23H2,1-11H3/t24-,25+,26+,27-,28-,29+,30+,31+,32-,33-,36-,37+,38-,39-,40-,41-,42-,43+,44-,55-,56-,57+,58-,59-,60+/m0/s1
• InChI Key: NWSULKNDMBRCNS-NSBUQMFKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₀H₈₈N₂O₂₃
• Molecular Weight: 1205.30 g/mol
• Exact Mass: 1204.57778706 g/mol
• Topological Polar Surface Area (TPSA): 333.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.38
• H-Bond Acceptor: 25
• H-Bond Donor: 9
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7720	77.20%
Caco-2	-	0.8606	86.06%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5476	54.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8814	88.14%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.8975	89.75%
P-glycoprotein inhibitior	+	0.7441	74.41%
P-glycoprotein substrate	+	0.7374	73.74%
CYP3A4 substrate	+	0.6902	69.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7920	79.20%
CYP3A4 inhibition	-	0.8686	86.86%
CYP2C9 inhibition	-	0.8649	86.49%
CYP2C19 inhibition	-	0.8507	85.07%
CYP2D6 inhibition	-	0.8474	84.74%
CYP1A2 inhibition	-	0.7309	73.09%
CYP2C8 inhibition	-	0.6587	65.87%
CYP inhibitory promiscuity	-	0.8922	89.22%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6002	60.02%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8977	89.77%
Skin irritation	-	0.7992	79.92%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	+	0.8046	80.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7328	73.28%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8949	89.49%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8238	82.38%
Acute Oral Toxicity (c)	II	0.6205	62.05%
Estrogen receptor binding	+	0.8137	81.37%
Androgen receptor binding	+	0.7697	76.97%
Thyroid receptor binding	+	0.6120	61.20%
Glucocorticoid receptor binding	+	0.8116	81.16%
Aromatase binding	+	0.6742	67.42%
PPAR gamma	+	0.8504	85.04%
Honey bee toxicity	-	0.7313	73.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8931	89.31%

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	99.61%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.43%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.38%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.67%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.17%	96.09%
CHEMBL4208	P20618	Proteasome component C5	89.89%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.86%	95.89%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	88.80%	85.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.43%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.97%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.07%	86.33%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.00%	96.37%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.96%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.85%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.68%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.75%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	80.27%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139589239
• LOTUS: LTS0112081
• wikiData: Q104402091