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121250-06-4 molecular structure
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(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(2-chloroacetyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

ChemBase ID: 164261
Molecular Formular: C27H28ClNO10
Molecular Mass: 561.96492
Monoisotopic Mass: 561.14017378
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](O)[C@H](N)C1)C)(C(=O)CCl)O)O)OC
Canonical SMILES:
ClCC(=O)[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
InChI:
InChI=1S/C27H28ClNO10/c1-10-22(31)13(29)6-17(38-10)39-15-8-27(36,16(30)9-28)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/h3-5,10,13,15,17,22,31,33,35-36H,6-9,29H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChIKey:
YPCKPOWJKPVJRQ-TZSSRYMLSA-N

Cite this record

CBID:164261 http://www.chembase.cn/molecule-164261.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(2-chloroacetyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
IUPAC Traditional name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-(2-chloroacetyl)-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
Synonyms
8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-8-(2-chloroacetyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
14-Chlorodaunomycin
14-Chlororubomycin
14-Chloro Daunorubicin
CAS Number
121250-06-4
PubChem SID
162258396
PubChem CID
14477608

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC C365655 external link Add to cart
PubChem 14477608 external link
Data Source Data ID Price
TRC
C365655 external link Add to cart Please log in.
Data Source Data ID
PubChem 14477608 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.530912  H Acceptors 11 
H Donor LogD (pH = 5.5) -0.08828281 
LogD (pH = 7.4) 1.0790293  Log P 2.2710261 
Molar Refractivity 137.6447 cm3 Polarizability 53.910458 Å3
Polar Surface Area 185.84 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
MSDS Link
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Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - C365655 external link
Adriamycin analogue; use as anticancer agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Krishan, A., et al.: Cancer Res., 41, 2745 (1981)
  • • Mueller, M., et al.: Eur. J. Biochem., 140, 447 (1981)
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PATENTS

PATENTS

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INTERNET

INTERNET

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