Doxorubicin
PubChem CID: 31703
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| Compound Synonyms | doxorubicin, Adriamycin, 23214-92-8, Adriablastin, Doxorubicine, Doxil, Adriblastina, Doxorubicinum, Doxorubicina, 14-Hydroxydaunomycin, 14-Hydroxydaunorubicine, Adriamycin semiquinone, Doxorubicine [INN-French], Doxorubicinum [INN-Latin], Doxorubicina [INN-Spanish], Hydroxydaunorubicin, CCRIS 739, HSDB 3070, NCI-C01514, NDC 38242-874, EINECS 245-495-6, FI 106, NSC 123127, CHEBI:28748, UNII-80168379AG, (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, CHEMBL53463, Caelyx (liposomal doxorubicin), 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)-, 80168379AG, DTXSID8021480, (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), (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, (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, ADM, Doxorubicine (INN-French), Doxorubicinum (INN-Latin), NSC-123127, Doxorubicina (INN-Spanish), DOXORUBICIN (MART.), DOXORUBICIN [MART.], (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, (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, (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, 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, hydroxydaunomycin, MLS000028393, DM2, 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, (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, 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)-, Adriblastina (TN), Doxorubicin-P4/D10, Doxorubicin (USAN/INN), VALRUBICIN IMPURITY, DOXORUBICIN (USP IMPURITY), VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY], Doxorubicin-hLL1 conjugate, doxorrubicina, Doxorubicin-P4/D10 conjugate, Doxorubicin?, ADR, Hydroxyldaunorubicin, Hydroxyl Daunorubicin, NSC123127, DOXORUBICIN [MI], Prestwick0_000438, Prestwick1_000438, Prestwick2_000438, Prestwick3_000438, DOXORUBICIN [INN], DOXORUBICIN [HSDB], DOXORUBICIN [USAN], Probes1_000151, Probes2_000129, DOXORUBICIN [VANDF], SCHEMBL3243, BSPBio_000456, BSPBio_001031, DOXORUBICIN [WHO-DD], 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, SPBio_002395, (8S-cis)-10-, BPBio1_000502, cid_443939, DTXCID301480, GTPL7069, Valrubicin impurity, doxorubicin, BDBM22984, BDBM32022, L01DB01, 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, BP-23114, NS00002473, (8S,10S)-10, (8S,10S)-10-, 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, 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-methyltetrahydro-2H-pyran-2-yloxy)-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)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroacetyl)-1-methoxy-5,12-naphthacenedione, (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, 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, 1392315-46-6, 245-495-6, 5,12-naphthacenedione, 10-((3-Amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro- 6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione |
|---|---|
| Topological Polar Surface Area | 206.0 |
| Hydrogen Bond Donor Count | 6.0 |
| Heavy Atom Count | 39.0 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 977.0 |
| Database Name | cmaup_ingredients;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 6.0 |
| Uniprot Id | P08684, Q16678, P10635, P20813, P33527, O95255, O15438, O95342, P08183, Q9UNQ0, Q86VW1, P11388, Q7ZJM1, n.a., P13945, P03905, P08253, O14746, P00375, Q02880, P10415, Q07817, Q9UBM7, P10844, A0JN73, Q04750, Q7YR26, P11387, P61823, P00639, O62855, P00970, P23940, P00642, P43870, P00640, O52691, Q92887, Q9H244, Q99814, O14965, Q9UBT6, P22309, O60656, P12530, P11229, P29466, P06241, P04626, P06239, P28564, O70528, Q5T3U5, Q96QA9, Q72547, O94956, Q9NPD5, Q9Y6L6, P16152, P14550, P18886, P32198, P27695, P02768, Q9NZ45, O15439, O88508, P31749, P31751 |
| 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 |
| Prediction Hob | 0.0 |
| Class | Carboxylic acids and derivatives |
| Target Id | NPT568, NPT980, NPT2796, NPT1044, NPT144, NPT143, NPT1432, NPT262, NPT277, NPT14, NPT286, NPT13, NPT1594, NPT668, NPT622, NPT72, NPT73, NPT1028, NPT322 |
| Xlogp | 1.3 |
| Superclass | Organic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Molecular Formula | C27H29NO11 |
| Prediction Swissadme | 0.0 |
| Inchi Key | AOJJSUZBOXZQNB-TZSSRYMLSA-N |
| Fcsp3 | 0.4444444444444444 |
| Logs | -2.69 |
| Rotatable Bond Count | 5.0 |
| State | Solid |
| Logd | 0.689 |
| Synonyms | (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, (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, 14-Hydroxydaunomycin, 14-Hydroxydaunorubicine, Adriamycin, Doxorubicine, Doxorubicinum, ADR, Adriblastina, (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-a-L-lyxo-hexopyranoside, (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-α-L-lyxo-hexopyranoside, (8S-cis)-10-((3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, (8S-cis)-10-((3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, Adriablastin, Adriblastin, Baxter brand OF doxorubicin hydrochloride, Doxorubicin hydrochloride, Doxorubicina ferrer farm, Ferrer brand OF doxorubicin hydrochloride, Onkoworks brand OF doxorubicin hydrochloride, Urokit doxo-cell, Ribosepharm brand OF doxorubicin hydrochloride, Adrimedac, Bedford brand OF doxorubicin hydrochloride, Doxorubicin hexal, Doxorubicin NC, Doxorubicina funk, Doxotec, Kenfarma brand OF doxorubicin hydrochloride, Prasfarma brand OF doxorubicin hydrochloride, Rubex, Tedec meiji brand OF doxorubicin hydrochloride, Cell pharm brand OF doxorubicin hydrochloride, Adriblastine, Columbia brand OF doxorubicin hydrochloride, Doxo cell, Doxo-cell, Elan brand OF doxorubicin hydrochloride, Farmiblastina, Lemery brand OF doxorubicin hydrochloride, Myocet, Onkodox, Ribodoxo, Adriablastine, Bristol-myers squibb brand OF doxorubicin hydrochloride, Doxolem, Doxorubicina tedec, Doxorubicine baxter, Hexal brand OF doxorubicin hydrochloride, Hydrochloride, doxorubicin, Neocorp brand OF doxorubicin hydrochloride, Pfizer brand OF doxorubicin hydrochloride, Urokit doxo cell, Medac brand OF doxorubicin hydrochloride |
| Compound Name | Doxorubicin |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 543.174 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 543.174 |
| Hydrogen Bond Acceptor Count | 12.0 |
| Molecular Weight | 543.5 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Esol | -3.9076473076923093 |
| 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 |
| Smiles | 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)CO)O)N)O |
| Nring | 5.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Gamma amino acids and derivatives |
- 1. Outgoing r'ship
FOUND_INto/from Alstonia Macrophylla (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Annona Bullata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Annona Cherimola (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Annona Cherimolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Annona Muricata (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Annona Squamosa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Atalantia Buxifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Austrobaileya Scandens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Bougainvillea Spectabilis (Plant) Rel Props:Source_db:npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Bursera Simaruba (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Carpesium Cernuum (Plant) Rel Props:Source_db:npass_chem_all - 12. Outgoing r'ship
FOUND_INto/from Cephalotaxus Fortunei (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 13. Outgoing r'ship
FOUND_INto/from Croton Tonkinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 14. Outgoing r'ship
FOUND_INto/from Croton Urucurana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 15. Outgoing r'ship
FOUND_INto/from Eurycoma Longifolia (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 16. Outgoing r'ship
FOUND_INto/from Goniothalamus Giganteus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 17. Outgoing r'ship
FOUND_INto/from Hesperocyparis Macrocarpa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 18. Outgoing r'ship
FOUND_INto/from Heynea Trijuga (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 19. Outgoing r'ship
FOUND_INto/from Ipomoea Nil (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 20. Outgoing r'ship
FOUND_INto/from Ipomoea Pes-Caprae (Plant) Rel Props:Source_db:npass_chem_all - 21. Outgoing r'ship
FOUND_INto/from Ixora Coccinea (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 22. Outgoing r'ship
FOUND_INto/from Melianthus Major (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 23. Outgoing r'ship
FOUND_INto/from Persea Americana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 24. Outgoing r'ship
FOUND_INto/from Physalis Peruviana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 25. Outgoing r'ship
FOUND_INto/from Schisandra Chinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 26. Outgoing r'ship
FOUND_INto/from Selaginella Moellendorffii (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 27. Outgoing r'ship
FOUND_INto/from Serenoa Repens (Plant) Rel Props:Source_db:npass_chem_all - 28. Outgoing r'ship
FOUND_INto/from Syzygium Nervosum (Plant) Rel Props:Source_db:cmaup_ingredients - 29. Outgoing r'ship
FOUND_INto/from Tamarix Aphylla (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 30. Outgoing r'ship
FOUND_INto/from Tinospora Sinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 31. Outgoing r'ship
FOUND_INto/from Viola Tricolor (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 32. Outgoing r'ship
FOUND_INto/from Xylopia Aromatica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all