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306387-90-6 molecular structure
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N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-yl]ethyl}-6-(3-phenylpropanamido)hexanamide

ChemBase ID: 172042
Molecular Formular: C44H63N3O4
Molecular Mass: 697.98872
Monoisotopic Mass: 697.48185751
SMILES and InChIs

SMILES:
C1(=O)CC2=CCC3C(C2(CC1)C)CC1=C(C2(CCC31)O[C@H]1C([C@H]2C)N(CC(C1)C)CCNC(=O)CCCCCNC(=O)CCc1ccccc1)C
Canonical SMILES:
CC1CN(CCNC(=O)CCCCCNC(=O)CCc2ccccc2)C2[C@@H](C1)OC1([C@@H]2C)CCC2C(=C1C)CC1C2CC=C2C1(C)CCC(=O)C2
InChI:
InChI=1S/C44H63N3O4/c1-29-25-39-42(47(28-29)24-23-46-40(49)13-9-6-10-22-45-41(50)17-14-32-11-7-5-8-12-32)31(3)44(51-39)21-19-35-36-16-15-33-26-34(48)18-20-43(33,4)38(36)27-37(35)30(44)2/h5,7-8,11-12,15,29,31,35-36,38-39,42H,6,9-10,13-14,16-28H2,1-4H3,(H,45,50)(H,46,49)/t29?,31-,35?,36?,38?,39-,42?,43?,44?/m1/s1
InChIKey:
WDHRPWOAMDJICD-BWBMXWGBSA-N

Cite this record

CBID:172042 http://www.chembase.cn/molecule-172042.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3'H-spiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-yl]ethyl}-6-(3-phenylpropanamido)hexanamide
IUPAC Traditional name
N-{2-[(3'R,7'aR)-3',6',10,11b-tetramethyl-3-oxo-1,2,3',3'a,4,5',6,6',6a,6b,7,7',7'a,8,11,11a-hexadecahydrospiro[cyclohexa[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-yl]ethyl}-6-(3-phenylpropanamido)hexanamide
Synonyms
KAAD-Cyclopamine
3-Keto-N-aminoethyl-N'-aminocaproyldihydrocinnamoyl Cyclopamine, >80%
CAS Number
306387-90-6
PubChem SID
164227952
PubChem CID
16760383

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC K171000 external link Add to cart
PubChem 16760383 external link
Data Source Data ID Price
TRC
K171000 external link Add to cart Please log in.
Data Source Data ID
PubChem 16760383 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 15.530833  H Acceptors
H Donor LogD (pH = 5.5) 2.878715 
LogD (pH = 7.4) 4.53552  Log P 5.9973145 
Molar Refractivity 204.6121 cm3 Polarizability 80.17164 Å3
Polar Surface Area 87.74 Å2 Rotatable Bonds 12 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

TRC TRC
Toronto Research Chemicals - K171000 external link
Cyclopamine demonstrates teratogenic properties and has been shown to reverse effects ofoncogenic mutations in Smoothened and Patched.1 The KAAD-Cyclopamine has shown 10-20 fold higher potency than cyclopamine in inhibition of β-Galactosidase expression in p2Ptch-1- cells, with similar or lower toxicity. KAAD-Cyclopamine compound is unstable in solution.

REFERENCES

REFERENCES

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  • • Taipale, J., et al.: Nature, 406, 1005 (2000)
  • • Perron, M., et al.: Development, 130, 1565 (2000)
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PATENTS

PATENTS

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INTERNET

INTERNET

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