EPIRUBICIN

Search structure
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01DB03
UNII: 3Z8479ZZ5X

Structure
InChI Key AOJJSUZBOXZQNB-VTZDEGQISA-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) 1.850 - EST
Henry's Law Constant 2.20E-23 atm-m3/mole EST
Atmospheric OH Rate Constant 1.45E-10 cm3/molecule-sec EST
Water Solubility 93 mg/L EST
Vapor Pressure 2.50E-23 mm Hg EST

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Isomerase
- 3 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 5181 - - -
Enzyme Protease Serine protease
- 750 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 7935 - 1323 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Nasopharyngeal Carcinoma 3 D000077274 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Triple Negative Breast Neoplasms 3 D064726 ClinicalTrials
Inflammatory Breast Neoplasms 3 D058922 ClinicalTrials
Thrombosis 3 D013927 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Sepsis 2 D018805 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 2 D009373 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Testicular Neoplasms 2 D013736 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Adenocarcinoma 2 D000230 ClinicalTrials
Thymoma 2 D013945 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 56420-45-2
ChEBI 47898
ChEMBL CHEMBL417
DrugBank DB00445
DrugCentral 1030
EPA CompTox DTXSID0022987
FDA SRS 3Z8479ZZ5X
Human Metabolome Database HMDB14588
KEGG C11230
PharmGKB PA449476
PubChem 41867
SureChEMBL SCHEMBL8582
ZINC ZINC000003938704
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