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23541-50-6 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 hydrochloride

ChemBase ID: 72636
Molecular Formular: C27H30ClNO10
Molecular Mass: 563.9808
Monoisotopic Mass: 563.15582385
SMILES and InChIs

SMILES:
c1ccc2c(c1OC)C(=O)c1c(C2=O)c(c2c(c1O)[C@H](C[C@](C2)(O)C(=O)C)O[C@H]1C[C@@H]([C@@H]([C@@H](O1)C)O)N)O.Cl
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.Cl
InChI:
InChI=1S/C27H29NO10.ClH/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;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
InChIKey:
GUGHGUXZJWAIAS-QQYBVWGSSA-N

Cite this record

CBID:72636 http://www.chembase.cn/molecule-72636.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 hydrochloride
IUPAC Traditional name
daunorubicin hydrochloride
Synonyms
(8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride
(8S-cis)-Daunomycin Hydrochloride
13-Dihydrocarminomycin
Cerubidine
Daunoblastin
Daunomycin Chlorohydrate
NDC 0082-4155
Ondena
RP 13057 Hydrochloride
Daunorubicin Hydrochloride
Daunomycin hydrochloride
Daunorubicin
Rubidomycin hydrochloride
Cerubidine
Daunorubicin hydrochloride
(-)-Daunorubicin
WP900 hydrochloride
Daunorubicin HCl (Daunomycin HCl)
Daunorubicinol hydrochloride
道诺霉素 盐酸盐
柔红霉素 盐酸盐
CAS Number
23541-50-6
EC Number
245-723-4
MDL Number
MFCD04974507
Beilstein Number
4229221
PubChem SID
24858374
24724666
162037561
24894229
PubChem CID
62770

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 7.996109  H Acceptors 11 
H Donor LogD (pH = 5.5) -0.49411148 
LogD (pH = 7.4) 0.9138854  Log P 1.3442496 
Molar Refractivity 132.8915 cm3 Polarizability 52.022972 Å3
Polar Surface Area 185.84 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
Dark Red Solid expand Show data source
solid expand Show data source
Melting Point
>180°C (dec) expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
HB7878000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
22-40-42/43 expand Show data source
Safety Statements
22-36/37-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H334-H351 expand Show data source
H302-H334-H351 expand Show data source
GHS Precautionary statements
P261-P281-P301 + P310-P342 + P311 expand Show data source
P261-P281-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Target
Telomerase expand Show data source
Topoisomerase expand Show data source
Purity
≥90% (HPLC) expand Show data source
≥95% (HPLC) expand Show data source
95+% expand Show data source
Salt Data
HCL expand Show data source
Hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Empirical Formula (Hill Notation)
C27H29NO10 · HCl expand Show data source
C27H30NO10Cl expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S1216 external link
Biological Activity:
Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is the hydrochloride salt of an anthracycline cytotoxic antibiotic produced by a strain of Streptomyces coeruleorubidus (IC50=0.5μM). On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) has the highest preference for two adjacent G/C base pairs flanked on the 5’ side by an A/T base pair. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) effectively binds to every 3 base pairs and induces a local unwinding angle of 11o, but negligible distortion of helical conformation. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is chemotherapeutic of the anthracycline family that is given as a treatment for some types of cancer. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is most commonly used to treat specific types of leukaemia (acute myeloid leukemia and acute lymphocytic leukemia). Cerubidine (Daunorubicin HCl, Rubidomycin HCl) was initially isolated from Streptomyces peucetius. [1][2][3]
Sigma Aldrich - 30450 external link
Biochem/physiol Actions
Daunorubicin inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Daunomycin effectively binds to every 3 base pairs which causes unwinding.
Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent. Properties
Application
Daunorubicin hydrochloride is used in photostability 1, antileukemic, 2, and drug metabolism studies 3.
Sigma Aldrich - W4013 external link
Biochem/physiol Actions
Synthetic left-handed enantiomer of (+)-daunorubicin, anti-tumor antibiotic, binds to right-handed B-form DNA under low salt conditions.
Sigma Aldrich - D8809 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
强效抗癌剂,已证明是 DNA 和 RNA 合成的强抑制剂。性质
自发荧光的蒽环类抗生素,抗癌药。Pgp、MRP-1 和 BCRP 的底物。已利用荧光特性来测量药物外排泵活性,以及解决许多重要问题,如多种多药耐药蛋白的胞内定位和亚细胞器(高尔基体和溶酶体)在药物螯合中的作用及其在耐药表型中的含义。根据 pH 分配型机理将柔红霉素螯合进溶酶体。1,2DNA 和 RNA 合成的强抑制剂。
Toronto Research Chemicals - D194500 external link
Anthracycline antibiotic related to the rhodomycins. Antineoplastic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://www.cancer.gov/drugdictionary/?CdrID=39779
  • • Yang, Z., et al.: J. Pharmacol. Experim. Ther., 327, 474 (2008)
  • • Zhao, Y., et al.: Int. J. Pharm., 379, 90 (2008)
  • • Bayne, W., et al.: J. Pharm. Sci., 98, 2540 (2008)
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PATENTS

PATENTS

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INTERNET

INTERNET

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