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153212-75-0 molecular structure
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(1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

ChemBase ID: 171028
Molecular Formular: C47H51NO15
Molecular Mass: 869.90554
Monoisotopic Mass: 869.32586994
SMILES and InChIs

SMILES:
C12=C([C@H](C[C@](C1(C)C)([C@H]([C@H]1[C@](C(=O)[C@@H]2OC(=O)C)([C@H]([C@@H]([C@@H]2[C@]1(CO2)OC(=O)C)O)O)C)OC(=O)c1ccccc1)O)OC(=O)[C@@H]([C@@H](NC(=O)c1ccccc1)c1ccccc1)O)C
Canonical SMILES:
CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)[C@H](O)[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
InChI:
InChI=1S/C47H51NO15/c1-24-30(61-43(57)33(51)32(27-16-10-7-11-17-27)48-41(55)28-18-12-8-13-19-28)22-47(58)40(62-42(56)29-20-14-9-15-21-29)36-45(6,38(54)35(60-25(2)49)31(24)44(47,4)5)37(53)34(52)39-46(36,23-59-39)63-26(3)50/h7-21,30,32-37,39-40,51-53,58H,22-23H2,1-6H3,(H,48,55)/t30-,32-,33+,34-,35+,36-,37-,39+,40-,45-,46+,47+/m0/s1
InChIKey:
NDCWHEDPSFRTDA-FJMWQILYSA-N

Cite this record

CBID:171028 http://www.chembase.cn/molecule-171028.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S,3R,4S,7R,8S,9R,10S,12R,15S)-4,12-bis(acetyloxy)-1,8,9-trihydroxy-15-{[(2R,3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate
IUPAC Traditional name
6α-hydroxypaclitaxel
Synonyms
6α-Hydroxy Taxol
6α-Hydroxy Paclitaxel
CAS Number
153212-75-0
PubChem SID
164226938
PubChem CID
10056458

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC H948890 external link Add to cart
PubChem 10056458 external link
Data Source Data ID Price
TRC
H948890 external link Add to cart Please log in.
Data Source Data ID
PubChem 10056458 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.862219  H Acceptors 11 
H Donor LogD (pH = 5.5) 2.8485265 
LogD (pH = 7.4) 2.847051  Log P 2.8485453 
Molar Refractivity 219.3916 cm3 Polarizability 87.20104 Å3
Polar Surface Area 241.52 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Off-White to Pale Pink Solid expand Show data source
Melting Point
177-180°C expand Show data source
Storage Condition
Refrigerator 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 - H948890 external link
The major human metabolite of Paclitaxel.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Walle, T., et al.: Biochem. Pharm., 46, 1661 (1993)
  • • Kumar, G., et al.: Drug Metab. Dispos., 22, 177 (1993)
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PATENTS

PATENTS

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INTERNET

INTERNET

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