Daunorubicin

Details

• Internal ID: 1f8a8579-fd69-4a84-b8f8-3ad5fea3c0f4
• Taxonomy: Phenylpropanoids and polyketides > Anthracyclines
• IUPAC Name: (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-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(=O)C)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(=O)C)O)N)O
• InChI: InChI=1S/C27H29NO10/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/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
• InChI Key: STQGQHZAVUOBTE-VGBVRHCVSA-N
• Popularity: 18,711 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₉NO₁₀
• Molecular Weight: 527.50 g/mol
• Exact Mass: 527.17914612 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 1.80

Synonyms

• Daunomycin
• 20830-81-3
• Acetyladriamycin
• Leukaemomycin C
• Rubidomycin
• Cerubidine
• (+)-Daunomycin
• DaunoXome
• Daunorubicinum
• Daunorubicine
• Cerubidin
• RP 13057
• Rubomycin C
• FI 6339
• Daunorubicin (INN)
• NSC-82151
• Daunarubicinum
• Daunorrubicina
• DaunoXome (TN)
• Daunamycin
• FI-6339
• FI6339
• ZS7284E0ZP
• (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
• DTXSID7022883
• CHEBI:41977
• RP-13057
• NCGC00024246-05
• Anthracycline
• Anthracyline
• NDC-0082-4155
• DAUNORUBICIN [INN]
• 5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
• Daunorubicinum [INN-Latin]
• DTXCID402883
• MLS000069508
• Daunorubicin [INN:BAN]
• NSC-83142
• RCRA waste no. U059
• (1S,3S)-3-acetyl-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
• (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• (8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• CAS-20830-81-3
• NSC82151
• SMR000058559
• CCRIS 914
• SR-01000000033
• SR-05000001600
• HSDB 5095
• NCI-C04693
• EINECS 244-069-7
• NSC 83142
• VS-103
• BRN 1445583
• Tocris-1467
• Daunorubicin(Daunomycin)
• AI3-52942
• Prestwick3_000487
• DAUNOMYCIN [IARC]
• DAUNORUBICIN [MI]
• CHEMBL178
• DAUNORUBICIN [HSDB]
• SCHEMBL3041
• DAUNORUBICIN [VANDF]
• EPIRUBICIN IMPURITY D
• UNII-ZS7284E0ZP
• BSPBio_000353
• DAUNORUBICIN [MART.]
• 5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S-cis)-
• cid_62770
• DAUNORUBICIN [WHO-DD]
• BPBio1_000389
• GTPL7063
• BDBM32017
• EX-A1337A
• Valrubicin impurity, daunorubicin
• STQGQHZAVUOBTE-VGBVRHCVSA-N
• Daunomycin;RP 13057;Rubidomycin
• DAUNORUBICIN [ORANGE BOOK]
• HMS2089H04
• HMS2091K06
• Pharmakon1600-01500223
• VYXEOS COMPONENT DAUNORUBICIN
• Tox21_110896
• BDBM50368352
• GR-318
• HY-13062A
• LMPK13050002
• MFCD00866340
• NSC756717
• Tox21_110896_1
• CCG-212559
• CS-2004
• DB00694
• NSC-756717
• NCGC00024246-06
• NCGC00024246-07
• NCGC00024246-09
• NCGC00024246-10
• NCGC00024246-12
• NCGC00024246-15
• NCGC00024246-18
• NCGC00025173-01
• (1S,3S)-3-acetyl-3,5,12-trihydroxy-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-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside
• (7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
• 5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
• SBI-0206677.P002
• AB00514669
• C01907
• D07776
• Epirubicin hydrochloride impurity, daunorubicin-
• AB00514669-09
• AB01644616_09
• AB01644616_10
• EN300-7479232
• A814957
• Q411659
• SR-01000000033-4
• SR-05000001600-1
• SR-05000001600-2
• BRD-K43389675-001-01-3
• BRD-K43389675-003-02-7
• BRD-K43389675-003-03-5
• BRD-K43389675-003-20-9
• EPIRUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
• VALRUBICIN IMPURITY, DAUNORUBICIN [USP IMPURITY]
• 2-HYDROXY-5-(4-NITRO-PHENYLSULFAMOYL)-BENZOICACID
• DOXORUBICIN HYDROCHLORIDE IMPURITY A [EP IMPURITY]
• EPIRUBICIN HYDROCHLORIDE IMPURITY, DAUNORUBICIN- [USP IMPURITY]
• (1S,3S)-3-ACETYL-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-LYXO-HEXOPYRANOSIDE
• (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-4-methoxy-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• (7S,9S)-9-acetyl-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione chloride
• (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride
• (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• (8S,10S)-8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE
• (8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro--6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
• 5,12-NAPHTHACENEDIONE, 8-ACETYL-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL))OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-, (8S-CIS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	631 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.66%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.41%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.28%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.47%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.41%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.67%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.11%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.57%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.47%	99.23%
CHEMBL2535	P11166	Glucose transporter	90.22%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.44%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.20%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.16%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	86.95%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.70%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.59%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.83%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.49%	96.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.98%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	83.75%	95.93%
CHEMBL3474	P14555	Phospholipase A2 group IIA	82.11%	94.05%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.50%	92.88%
CHEMBL4208	P20618	Proteasome component C5	81.11%	90.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.89%	94.42%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 30323
• LOTUS: LTS0090706
• wikiData: Q411659