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20830-81-3 molecular structure
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(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

ChemBase ID: 576
Molecular Formular: C27H29NO10
Molecular Mass: 527.51986
Monoisotopic Mass: 527.17914613
SMILES and InChIs

SMILES:
O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2)C(=O)C)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
Canonical SMILES:
COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
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
InChIKey:
STQGQHZAVUOBTE-VGBVRHCVSA-N

Cite this record

CBID:576 http://www.chembase.cn/molecule-576.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
IUPAC Traditional name
daunorubicin
Brand Name
Acetyladriamycin
Anthracyline
Antibiotics From Streptomyces Coeruleorubidus
Cerubidin
Cerubidine
DM1
Daunamycin
Daunarubicinum
Daunoblastin
Daunomycin
Daunomycin Hydrochloride
Daunomycin, Hydrochloride
Daunorrubicina
Daunorubicin Hcl
Daunorubicin Hydrochloride
Daunorubicin, Hydrochloride
Daunorubicine
Daunorubicinum [INN-Latin]
Daunoxome
Leukaemomycin C
Ondena
Rcra Waste No. U059
Rp 13057 Hydrochloride
Rubidomycin
Rubidomycin Hydrochloride
Rubomycin C
Synonyms
Daunorubicin
CAS Number
20830-81-3
PubChem SID
160964039
46508433
PubChem CID
30323
CHEBI ID
41977
ATC CODE
L01DB02
CHEMBL
178
Chemspider ID
28163
DrugBank ID
DB00694
KEGG ID
C01907
Unique Ingredient Identifier
ZS7284E0ZP
Wikipedia Title
Daunorubicin
Medline Plus
a682289

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.530939  H Acceptors 11 
H Donor LogD (pH = 5.5) -0.6256268 
LogD (pH = 7.4) 0.54168487  Log P 1.7336931 
Molar Refractivity 132.8915 cm3 Polarizability 52.022972 Å3
Polar Surface Area 185.84 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 1.68  LOG S -2.93 
Solubility (Water) 6.27e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
39.2 mg/L expand Show data source
Hydrophobicity(logP)
0.1 expand Show data source
Admin Routes
Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously expand Show data source
Excretion
Biliary and urinary expand Show data source
Half Life
26.7 hours (metabolite) expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
D (U.S.) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00694 external link
Item Information
Drug Groups approved
Description A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]
Indication For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.
Pharmacology Daunorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Half Life 18.5 hours
Protein Binding 97% binding-albumin
Elimination Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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