Home > Compound List > Compound details
152044-54-7 molecular structure
click picture or here to close

(1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

ChemBase ID: 168108
Molecular Formular: C27H41NO6S
Molecular Mass: 507.68254
Monoisotopic Mass: 507.26545904
SMILES and InChIs

SMILES:
[C@@H]12[C@@](CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](CC(=O)OC(C1)/C(=C/c1csc(n1)C)/C)O)(C)C)C)O)C)(O2)C
Canonical SMILES:
O=C1OC(C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
InChI:
InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20?,21-,22-,24-,27+/m0/s1
InChIKey:
QXRSDHAAWVKZLJ-HPZHUWBASA-N

Cite this record

CBID:168108 http://www.chembase.cn/molecule-168108.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
IUPAC Traditional name
(1S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Synonyms
(-)-Epothilone B
EPO 906
EPO 906A
Epothilone B
Patupilone
Epothilone B (synthetic)
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
CAS Number
152044-54-7
PubChem SID
162262240
PubChem CID
60018621

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC E588990 external link Add to cart
PubChem 60018621 external link
Data Source Data ID Price
TRC
E588990 external link Add to cart Please log in.
Data Source Data ID
PubChem 60018621 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.086929  H Acceptors
H Donor LogD (pH = 5.5) 4.122024 
LogD (pH = 7.4) 4.1227245  Log P 4.1227336 
Molar Refractivity 134.76 cm3 Polarizability 53.40498 Å3
Polar Surface Area 105.95 Å2 Rotatable Bonds
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
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White Powder expand Show data source
Melting Point
95-97°C expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere 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 - E588990 external link
Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the c

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bollag, D.M., et al.: Cancer. Res., 55, 2325 (1995)
  • • Hardt, I.H., et al.: J. Nat. Prod., 64, 847 (1995)
  • • Gerth, K., et al.: J. Antibiot., 55, 41, 45 (2002)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle