Doxorubicin

Details

• Internal ID: b6a6474a-ed1b-4763-bb2c-84708492549a
• 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-(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-TZSSRYMLSA-N
• Popularity: 132,224 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

• Adriamycin
• 23214-92-8
• Adriablastin
• Doxorubicine
• Doxorubicinum
• Doxorubicina
• 14-Hydroxydaunomycin
• 14-Hydroxydaunorubicine
• NDC 38242-874
• CHEBI:28748
• NSC 123127
• (7S,9S)-7-[(2R,4S,5S,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
• NSC-759155
• 80168379AG
• DTXSID8021480
• NSC-123127
• (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
• 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
• (8S,10S)-10-{[(2R,4S,5S,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
• (8S-cis)-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
• hydroxydaunomycin
• doxorrubicina
• Adriablastine
• Hydroxyldaunorubicin
• (7S,9S)-7-((2R,4S,5S,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,5S,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
• Hydroxyl Daunorubicin
• RefChem:5780
• DTXCID301480
• L01DB01
• (8S-cis)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroacetyl)-1-methoxy-5,12-naphthacenedione
• 245-495-6
• KW-125
• Doxil
• Adriblastina
• Doxorubicine [INN-French]
• Doxorubicinum [INN-Latin]
• Doxorubicina [INN-Spanish]
• Hydroxydaunorubicin
• Adriamycin semiquinone
• Caelyx
• MFCD00869292
• CHEMBL53463
• NCI-C01514
• ADM
• (7S,9S)-7-[(2R,4S,5S,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
• (8S,10S)-10-(((2R,4S,5S,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-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
• Doxorubicin [USAN:INN:BAN]
• ThermoDox
• MLS000028393
• Doxorubicin-hLL1
• (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-lyxo-hexopyranoside
• (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-lyxo-hexopyranoside
• Adriblastina (TN)
• CCRIS 739
• Doxorubicin-P4/D10
• HSDB 3070
• EINECS 245-495-6
• Doxorubicin (USAN/INN)
• Doxorubicin-hLL1 conjugate
• Doxorubicin-P4/D10 conjugate
• Doxorubicin?
• UNII-80168379AG
• DOXORUBICIN [MI]
• Prestwick0_000438
• Prestwick1_000438
• Prestwick2_000438
• Prestwick3_000438
• DOXORUBICIN [INN]
• ADR
• DOXORUBICIN [HSDB]
• DOXORUBICIN [USAN]
• Probes1_000151
• Probes2_000129
• DOXORUBICIN [VANDF]
• SCHEMBL3243
• DOXORUBICIN [MART.]
• BSPBio_000456
• BSPBio_001031
• DOXORUBICIN [WHO-DD]
• (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-tridesoxy-alpha-L-lyxo-hexopyranosid)
• (8S,10S)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• 1,2,3,4,6,11-Hexahydro-4beta,5,12-trihydroxy-4-(hydroxyacetyl)-10-methoxy-6,11-dioxonaphthacen-1beta-yl-3-amino-2,3,6-trideoxy-alpha-L-lyxohexopyranoside
• 10-((3-Amino-2,3,6-trideoxy-D-lyxohexopyranosyl)oxy)-8-glycolcyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• Caelyx (liposomal doxorubicin)
• SPBio_002395
• BPBio1_000502
• cid_443939
• GTPL7069
• orb1308571
• orb2279710
• Valrubicin impurity, doxorubicin
• SCHEMBL29459849
• BDBM22984
• BDBM32022
• HMS2089H06
• (8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE
• 5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-
• GR-319
• HY-15142A
• LMPK13050001
• AKOS015951330
• Conjugate of doxorubicin with humanized monoclonal antibody LL1 against CD74
• Conjugate of doxorubicin with monoclonal antibody P4/D10 against GP120
• DB00997
• SMP1_000106
• NCGC00024415-35
• NCGC00024415-37
• NCGC00024415-38
• NCGC00024415-40
• NCGC00024415-41
• NCGC00024415-42
• NCGC00024415-61
• AC-37453
• BP-23114
• BP-44119
• SY224845
• NS00002473
• 14D928
• C01661
• D03899
• EN300-120698
• Epirubicin hydrochloride impurity, doxorubicin-
• H11954
• Q18936
• BRD-K92093830-003-04-3
• BRD-K92093830-003-25-8
• BRD-K92093830-003-30-8
• BRD-K92093830-003-31-6
• BRD-K92093830-003-33-2
• VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY]
• EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP IMPURITY]
• DAUNORUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
• EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP IMPURITY]
• (7S,9R)-7-[(2S,4S,5S,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
• (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-9-glycoloyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride
• (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-4-methoxy-6,9,11-tris(oxidanyl)-9-(2-oxidanylethanoyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• (7S,9S)-7-[(4S,5S,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
• (7S,9S)-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• (8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-2-tetrahydropyranyl]oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
• 1392315-46-6
• 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
• 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-|A-L-lyxo-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
CHEMBL4860	P10415	Apoptosis regulator Bcl-2	26000 nM	GI50	PMID: 17181155
CHEMBL4625	Q07817	Apoptosis regulator Bcl-X	24000 nM	GI50	PMID: 17181155
CHEMBL4801	P29466	Caspase-1	12192 nM	IC50	via CMAUP
CHEMBL1781	P11387	DNA topoisomerase I	20000 nM	IC50	PMID: 20662543
CHEMBL1806	P11388	DNA topoisomerase II alpha	1000 nM; 1000 nM; 880 nM	IC50; IC50; IC50	PMID: 11430001; PMID: 11430001; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	794.3 nM	Potency	via Super-PRED
CHEMBL333	P08253	Matrix metalloproteinase-2	1100 nM	IC50	PMID: 1322986
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	50000 nM	IC50	PMID: 8621644
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	15336 nM	IC50	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	8500 nM	Ki	PMID: 11405287
CHEMBL1824	P04626	Receptor protein-tyrosine kinase erbB-2	2485 nM	IC50	via CMAUP
CHEMBL4722	O14965	Serine/threonine-protein kinase Aurora-A	40 nM	IC50	PMID: 21664013
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	41000 nM	IC50	PMID: 22541068
CHEMBL1293232	Q16637	Survival motor neuron protein	891.3 nM; 281.8 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	5147 nM	IC50	via CMAUP
CHEMBL258	P06239	Tyrosine-protein kinase LCK	31913 nM	IC50	via CMAUP

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

• Dracocephalum kotschyi
• Ixora coccinea

Cross-Links

• PubChem: 31703
• NPASS: NPC261012
• ChEMBL: CHEMBL53463
• LOTUS: LTS0044264
• wikiData: Q18936