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76155-56-1 molecular structure
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(8S,10S)-10-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

ChemBase ID: 168096
Molecular Formular: C27H31NO11
Molecular Mass: 545.53514
Monoisotopic Mass: 545.18971082
SMILES and InChIs

SMILES:
c1ccc(c2c1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@H]1O[C@H]([C@@H]([C@@H](C1)N)O)C)(C(CO)O)O)O)OC
Canonical SMILES:
OCC([C@@]1(O)C[C@H](O[C@@H]2C[C@@H](N)[C@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC)O
InChI:
InChI=1S/C27H31NO11/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-,16?,17+,22-,27-/m0/s1
InChIKey:
NKZRZOVSJNSBFR-FIQSUXTJSA-N

Cite this record

CBID:168096 http://www.chembase.cn/molecule-168096.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(8S,10S)-10-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
IUPAC Traditional name
(8S,10S)-10-{[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
Synonyms
Epirubicinol, 60% (Contains Unknown Salts)(Mixture of Diastereomers)
10-[(3-Amino-2,36,-trideoxy-α-L-arabino-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-(8S,10S)-5,12-naphthacenedione Citrate
13-Dihydroadriamycin Citrate
CAS Number
76155-56-1
PubChem SID
162262228
PubChem CID
71316367

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC E588655 external link Add to cart
PubChem 71316367 external link
Data Source Data ID Price
TRC
E588655 external link Add to cart Please log in.
Data Source Data ID
PubChem 71316367 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.7360735  H Acceptors 12 
H Donor LogD (pH = 5.5) -2.0881715 
LogD (pH = 7.4) -1.0748831  Log P 0.22790514 
Molar Refractivity 135.3604 cm3 Polarizability 53.158913 Å3
Polar Surface Area 209.23 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Apperance
Dark Red Solid expand Show data source
Melting Point
>200°C (dec.) expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - E588655 external link
A metabolite of Epirubicin, a neoplasm inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Salvatorelli, E., et al.: J. Biol. Chem., 281, 10990 (2006)
  • • Salvatorelli, E., et al.: J. Pharmacol. Exper. Ther., 320, 790 (2006)
  • • Efferth, T., et al.: Clin. Cancer Res., 14, 2405 (2006)
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PATENTS

PATENTS

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INTERNET

INTERNET

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