13-Dihydrodaunorubicin

Details

• Internal ID: 926c7e4e-8798-4f46-a4b5-bbf36711793b
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• SMILES (Canonical): CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(C)O)O)N)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(C)O)O)N)O
• InChI: InChI=1S/C27H31NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10-11,14,16-17,22,29-30,32,34-35H,7-9,28H2,1-3H3/t10-,11?,14-,16-,17-,22+,27-/m0/s1
• InChI Key: HJEZFVLKJYFNQW-FKKRWUELSA-N
• Popularity: 74 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₁NO₁₀
• Molecular Weight: 529.50 g/mol
• Exact Mass: 529.19479619 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 0.82
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• CHEBI:31059
• (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• (7S,9S)-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• RefChem:1057466
• Daunorubicin EP Impurity B
• SCHEMBL1136412
• CHEMBL3544589
• DTXSID20950699
• LMPK13050004
• Epirubicin Hydrochloride EP Impurity E
• V73O8640X8
• ID183436
• Q27114110
• DAUNORUBICIN HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• (1S,3S)-3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
• (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• (8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-8-((1RS)-1-HYDROXYETHYL)-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE
• (8S,10S)-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,8,11-trihydroxy-8-((1rs)-1-hydroxyethyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• (8S,10S)-10-[(3-amino-2,3,6-trideoxy-|A-L-lyxo-hexopyranosyl)oxy]-6,8,11-trihydroxy-8-[(1RS)-1- hydroxyethyl]-1-methoxy-7,8,9,10-tetrahydrotetracene- 5,12-dione (dihydrodaunorubicin)
• 3,5,12-trihydroxy-3-(1-hydroxyethyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxyhexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7316	73.16%
Caco-2	-	0.8137	81.37%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Nucleus	0.7949	79.49%
OATP2B1 inhibitior	-	0.8705	87.05%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7104	71.04%
P-glycoprotein inhibitior	-	0.6220	62.20%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6773	67.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8001	80.01%
CYP3A4 inhibition	-	0.9157	91.57%
CYP2C9 inhibition	-	0.9448	94.48%
CYP2C19 inhibition	-	0.9527	95.27%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8777	87.77%
CYP2C8 inhibition	-	0.9190	91.90%
CYP inhibitory promiscuity	-	0.9543	95.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5598	55.98%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.8003	80.03%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6086	60.86%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8821	88.21%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5690	56.90%
Acute Oral Toxicity (c)	II	0.7589	75.89%
Estrogen receptor binding	+	0.8973	89.73%
Androgen receptor binding	+	0.7997	79.97%
Thyroid receptor binding	+	0.5188	51.88%
Glucocorticoid receptor binding	+	0.8555	85.55%
Aromatase binding	+	0.8060	80.60%
PPAR gamma	+	0.8678	86.78%
Honey bee toxicity	-	0.6320	63.20%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8399	83.99%

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	99.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.06%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.91%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.72%	95.56%
CHEMBL2535	P11166	Glucose transporter	93.61%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.48%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.75%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.64%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.32%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.32%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.70%	97.14%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.66%	92.88%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.21%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.36%	94.45%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.19%	96.86%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.16%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.44%	90.24%
CHEMBL226	P30542	Adenosine A1 receptor	84.21%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.21%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.94%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.84%	90.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.49%	100.00%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.40%	95.69%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.00%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.56%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.99%	96.21%
CHEMBL221	P23219	Cyclooxygenase-1	80.92%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	80.28%	98.03%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.09%	83.10%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.05%	96.77%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 83845
• LOTUS: LTS0152701
• wikiData: Q27114110