DOXORUBICIN

Search structure
Synonyms:
Status: Approved (1974)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01DB01
UNII: 80168379AG

Structure
InChI Key AOJJSUZBOXZQNB-TZSSRYMLSA-N
Smile COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H29NO11
Molecular Weight 543.53
AlogP 0.0
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 5.0
Polar Surface Area 206.07
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 39.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 1.27 - EXP
Henry's Law Constant 2.23E-23 atm-m3/mole EST
Atmospheric OH Rate Constant 1.45E-10 cm3/molecule-sec EST
Melting Point 229-231 deg C EXP
Water Solubility 92.8 mg/L EST
Vapor Pressure 8.99E-25 mm Hg EST

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 900-2400 - - -
Enzyme Isomerase
- 1200-3800 - - 0-72
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase AUR family
- 40 - - -
Enzyme Oxidoreductase
- 150-300 - - -
Enzyme Protease Metallo protease Metallo protease MAM clan Metallo protease M10A subfamily
- 1100 - - -
Enzyme Transferase
- 73000 - - -
Enzyme
- 1200-3800 - - 0-72
Epigenetic regulator Writer DNA methyltransferase
- 3000 - - 70
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Purine receptor
- - - - 7
Transcription factor
120 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 41000 - 38000 27-54
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 19000 - - -
Unclassified protein
- 80760 - 3451 -

Metabolites

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Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 3 D015459 ClinicalTrials
Peritoneal Neoplasms 3 D010534 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Hepatoblastoma 3 D018197 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Immunoblastic Lymphadenopathy 3 D007119 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Neutropenia 3 D009503 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Peritoneal Neoplasms 3 D010534 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Fallopian Tube Neoplasms 3 D005185 ClinicalTrials
Liver Neoplasms 3 D008113 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Liver Neoplasms 3 D008113 ClinicalTrials
Choroid Plexus Neoplasms 3 D016545 ClinicalTrials
Sarcoma, Kaposi 3 D012514 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Leiomyosarcoma 3 D007890 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Endometrial Neoplasms 3 D016889 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Osteosarcoma 3 D012516 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Carcinoma 3 D002277 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Triple Negative Breast Neoplasms 3 D064726 ClinicalTrials
Endometrial Neoplasms 3 D016889 ClinicalTrials
Waldenstrom Macroglobulinemia 3 D008258 ClinicalTrials
Inflammatory Breast Neoplasms 3 D058922 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Retinoblastoma 3 D012175 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 3 D015451 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Fallopian Tube Neoplasms 3 D005185 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Granuloma, Lethal Midline 3 D006103 ClinicalTrials
Neuroendocrine Tumors 2 D018358 ClinicalTrials
Leukemia, Lymphoid 2 D007945 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Carcinoma, Adenoid Cystic 2 D003528 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Mesothelioma 2 D008654 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Mesothelioma 2 D008654 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Cholangiocarcinoma 2 D018281 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Hereditary Breast and Ovarian Cancer Syndrome 2 D061325 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Optic Nerve Glioma 2 D020339 ClinicalTrials
Carcinoma, Intraductal, Noninfiltrating 2 D002285 ClinicalTrials
Ganglioneuroblastoma 2 D018305 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Carcinosarcoma 2 D002296 ClinicalTrials
Uterine Cervical Neoplasms 2 D002583 ClinicalTrials
Salivary Gland Neoplasms 2 D012468 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Lymphoma, T-Cell 2 D016399 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Wilms Tumor 2 D009396 ClinicalTrials
Hemangiosarcoma 2 D006394 ClinicalTrials
Urethral Neoplasms 1 D014523 ClinicalTrials
Lymphoma, B-Cell 1 D016393 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 1 D016410 ClinicalTrials
Hematologic Diseases 1 D006402 ClinicalTrials
Thymoma 1 D013945 ClinicalTrials
Thymoma 1 D013945 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Carcinoma, Pancreatic Ductal 1 D021441 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Bone Neoplasms 1 D001859 ClinicalTrials
Castleman Disease 1 D005871 ClinicalTrials
Breast Neoplasms, Male 1 D018567 ClinicalTrials
Amyloidosis 1 D000686 ClinicalTrials
Breast Carcinoma In Situ 1 D000071960 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 23214-92-8
ChEBI 28748
ChEMBL CHEMBL53463
DrugBank DB00997
DrugCentral 960
EPA CompTox DTXSID8021480
FDA SRS 80168379AG
Human Metabolome Database HMDB0015132
Guide to Pharmacology 7069
KEGG C01661
PDB DM2
PharmGKB PA449412
PubChem 31703
SureChEMBL SCHEMBL3243
ZINC ZINC000003918087
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