Compound: daunorubicin
SMILES: O=C1c2c(O)c3c(C[C@@](O)(C(=O)C)C[C@@H]3O[C@@H]4O[C@H]([C@@H](O)[C@H](C4)N)C)c(c2C(=O)c5c1c(OC)ccc5)O
InChIKey: STQGQHZAVUOBTE-VGBVRHCVSA-N
Synonyms: daunorubicin, Daunomycin, 20830-81-3, Acetyladriamycin, Leukaemomycin C, Daunorubicine, Rubidomycin, (+)-Daunomycin, Rubomycin C, Daunarubicinum, Daunorrubicina, Daunamycin, Daunorubicinum, Cerubidin, RP 13057, FI6339, Daunorubicina, FI 6339, RP-13057, NSC-83142, FI-6339, ZS7284E0ZP, DTXSID7022883, NCI-C04693, (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,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, (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, DTXCID402883, CHEBI:41977, VYXEOS COMPONENT DAUNORUBICIN, NSC 82151, Dauno-Rubidomycine, 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)-, 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)-, daunomicina, Dauno Rubidomycine, (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,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, RefChem:919679, L01DB02, (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, 244-069-7, L-lyxo-Hexopyranoside, 3beta-acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-metldioxo-1a-naphthacenyl 3-amino-2,3,6-trideoxy-,alpha-, Cerubidine, DaunoXome, Daunorubicin (INN), DaunoXome (TN), MFCD00866340, NCGC00024246-05, Anthracyline, DAUNORUBICIN [INN], (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, (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-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-, Daunorubicinum [INN-Latin], MLS000069508, Daunorubicin [INN:BAN], RCRA waste no. U059, (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, CAS-20830-81-3, SMR000058559, CCRIS 914, SR-01000000033, SR-05000001600, HSDB 5095, EINECS 244-069-7, NSC 83142, VS-103, BRN 1445583, Tocris-1467, Daunorubicin(Daunomycin), AI3-52942, (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, Prestwick3_000487, DAUNOMYCIN [IARC], DAUNORUBICIN [MI], CHEMBL178, DAUNORUBICIN [HSDB], SCHEMBL3041, DAUNORUBICIN [VANDF], EPIRUBICIN IMPURITY D, UNII-ZS7284E0ZP, BSPBio_000353, DAUNORUBICIN [MART.], cid_62770, orb611916, DAUNORUBICIN [WHO-DD], BPBio1_000389, GTPL7063, orb3029193, SCHEMBL29354538, SCHEMBL29996035, BDBM32017, EX-A1337A, Valrubicin impurity, daunorubicin, Daunomycin;RP 13057;Rubidomycin, DAUNORUBICIN [ORANGE BOOK], GLXC-23059, HMS2089H04, HMS2091K06, Pharmakon1600-01500223, Tox21_110896, BDBM50368352, EBC-27278, GR-318, HY-13062A, LMPK13050002, NSC756717, Tox21_110896_1, CCG-212559, CS-2004, DB00694, MD32002, 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, (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, SBI-0206677.P002, AB00514669, C01907, D07776, Epirubicin hydrochloride impurity, daunorubicin-, AB00514669-09, AB01644616_09, AB01644616_10, EN300-7479232, Q411659, SR-01000000033-4, SR-05000001600-1, SR-05000001600-2, BRD-K43389675-001-01-3, BRD-K43389675-001-02-1, BRD-K43389675-003-02-7, BRD-K43389675-003-03-5, BRD-K43389675-003-16-7, BRD-K43389675-003-20-9, EPIRUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY], VALRUBICIN IMPURITY, DAUNORUBICIN [USP IMPURITY], 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, (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, (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-[(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-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, (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-n aphthacenedione, 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)-, Doxorubicin Hydrochloride EP Impurity A; Epirubicin hydrochloride EP Impurity D; (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
Theoretical properties:
molecular_formula: C27H29NO10
molecular_weight: 527.5 g/mol
exact_mass: 527.17914612 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 4
heavy_atom_count: 38
topological_polar_surface_area: 186 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Reddish needles
color: Reddish needles
melting_point: 208-209 °C
vapor_pressure: 9.4X10-15 mm Hg at 25 °C
Descriptions:
pubchem: Daunomycin can cause cancer according to an independent committee of scientific and health experts.
chebi: A natural product found in <em>Actinomadura roseola</em>.
chembl: DAUNORUBICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is administered by injection into a vein. A liposomal formulation known as liposomal daunorubicin also exists.
Common side effects include hair loss, vomiting, bone marrow suppression, and inflammation of the inside of the mouth. Other severe side effects include heart disease and tissue death at the site of injection. Use in pregnancy may harm the fetus. Daunorubicin is in the anthracycline family of medication. It works in part by blocking the function of topoisomerase II.
Daunorubicin was approved for medical use in the United States in 1979. It is on the World Health Organization's List of Essential Medicines.  It was originally isolated from bacteria of the Streptomyces type.