Epirubicin

Details

• Internal ID: 91febbfd-5cf7-4cc0-ad86-49115f850baa
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• InChI: InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1
• InChI Key: AOJJSUZBOXZQNB-VTZDEGQISA-N
• Popularity: 18,267 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₉NO₁₁
• Molecular Weight: 543.50 g/mol
• Exact Mass: 543.17406074 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 56420-45-2
• Epiadriamycin
• Epidoxorubicin
• 4'-Epiadriamycin
• Epirubicine
• Epirubicina
• Ridorubicin
• Epirubicinum
• Pidorubicina
• Pidorubicine
• Pidorubicinum
• 4'-epidoxorubicin
• Farmorubicin
• Epirubicinum [Latin]
• Pidorubicin
• IMI 28
• NSC-256942
• 4'-epi-Doxorubicin
• NSC 256942
• 3Z8479ZZ5X
• (8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• DTXSID0022987
• CHEBI:47898
• NSC256942
• Epirubicinum (Latin)
• (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 4' Epi Adriamycin
• 4'-Epi-DXR
• Farmorubicine
• EPIcell
• 4' Epiadriamycin
• EPI cell
• 4' Epidoxorubicin
• (7S,9S)-7-((2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• (8S,10S)-10-(((2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• Epi DX
• 4' Epi Doxorubicin
• RefChem:55117
• 4'-epi DX
• 4' Epi DXR
• DTXCID202987
• L01DB03
• 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
• (1S,3S)-3-GLYCOLOYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-10-METHOXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-alpha-L-ARABINO-HEXOPYRANOSIDE
• (8S-cis)-10-((3-Amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
• 3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside
• Pharmorubicin
• 4-Epidoxorubicin
• Epirubicin free base
• Epirubicin (INN)
• Epi-DX
• Epirubicine [French]
• Epirubicina [Spanish]
• (8S,10S)-10-(((2R,4S,5R,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
• Epirubicine [INN-French]
• Epirubicinum [INN-Latin]
• Epirubicina [INN-Spanish]
• Pidorubicine [INN-French]
• Pidorubicinum [INN-Latin]
• 56420-45-2 (FREE BASE)
• Pidorubicina [INN-Spanish]
• EPIRUBICIN [INN]
• Epirubicin [INN:BAN]
• (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside
• WP 697
• (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• Farmorubicin (TN)
• CCRIS 2261
• HSDB 6962
• BRN 1445813
• Epi-doxorubicin
• UNII-3Z8479ZZ5X
• DM6
• Acid, 8
• EPIRUBICIN [MI]
• EPIRUBICIN [HSDB]
• EPIRUBICIN [VANDF]
• CHEMBL417
• SCHEMBL8582
• EPIRUBICIN [WHO-DD]
• orb1740387
• SCHEMBL29350836
• SCHEMBL29711855
• BDBM43839
• Doxorubicin-13CD3 (discontinued)
• DM2
• EBC-27300
• DB00445
• NCGC00263918-04
• NCGC00263918-06
• NCGC00263918-08
• (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside
• (7S,9R)-7-[(2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione
• 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
• BP-43652
• HY-13624
• SBI-0206890.P001
• NS00069619
• D07901
• AB00698552-11
• AB00698552-13
• AB00698552-14
• AB00698552_15
• AB00698552_16
• EN300-7410311
• Q425122
• BRD-K04548931-003-13-2
• BRD-K04548931-003-16-5
• (1S,3S)-3-GLYCOLOYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-10-METHOXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSIDE
• 5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-ARABINO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-
• 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6934	69.34%
Caco-2	-	0.8650	86.50%
Blood Brain Barrier	-	0.9750	97.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Nucleus	0.8460	84.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9008	90.08%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8067	80.67%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.9478	94.78%
CYP3A4 substrate	+	0.7321	73.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8188	81.88%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9209	92.09%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8911	89.11%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6246	62.46%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.8099	80.99%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	+	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5316	53.16%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8644	86.44%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7766	77.66%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8760	87.60%
Thyroid receptor binding	-	0.5173	51.73%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.8338	83.38%
PPAR gamma	+	0.7875	78.75%
Honey bee toxicity	-	0.6879	68.79%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7312	73.12%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL612409	Q15125	Anti-estrogen binding site (AEBS)	150 nM	IC50	via Super-PRED
CHEMBL1806	P11388	DNA topoisomerase II alpha	880 nM	IC50	via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	794.3 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	281.8 nM; 891.3 nM	Potency; Potency	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	98.23%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.96%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.78%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	94.30%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.80%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.96%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.74%	99.23%
CHEMBL2535	P11166	Glucose transporter	88.40%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.14%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.69%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.10%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.07%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.32%	92.94%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.49%	92.88%
CHEMBL340	P08684	Cytochrome P450 3A4	81.56%	91.19%
CHEMBL4208	P20618	Proteasome component C5	80.20%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.10%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.00%	96.95%

Plants that contains it

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Cross-Links

• PubChem: 41867
• LOTUS: LTS0163211
• wikiData: Q425122