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83602-41-9 molecular structure
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(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl acetate

ChemBase ID: 165286
Molecular Formular: C31H57N3O5
Molecular Mass: 551.80138
Monoisotopic Mass: 551.42982194
SMILES and InChIs

SMILES:
C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)C([C@@H](C/C=C/C)C)OC(=O)C
Canonical SMILES:
C/C=C/C[C@H](C(C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)OC(=O)C)C
InChI:
InChI=1S/C31H57N3O5/c1-11-12-17-23(6)30(39-24(7)35)29(34(9)10)27(37)19-16-14-13-15-18-26(36)28(22(4)5)33-31(38)25(32-8)20-21(2)3/h11-12,21-23,25,28-30,32H,13-20H2,1-10H3,(H,33,38)/b12-11+/t23-,25+,28+,29?,30?/m1/s1
InChIKey:
MJAWNADQWQTPRP-IUUVSZEYSA-N

Cite this record

CBID:165286 http://www.chembase.cn/molecule-165286.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl acetate
IUPAC Traditional name
(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxooctadec-2-en-6-yl acetate
Synonyms
6-[(2S,3R,4R,6E)-3-(Acetyloxy)-4-methyl-2-(methylamino)-6-octenoic acid] Cyclosporin A
B 3-243
O-Acetyl-C91-cyclosporin A
O-Acetylcyclosporin A
SDZ 33-243
Cyclosporin A Acetate
CAS Number
83602-41-9
PubChem SID
162259419
PubChem CID
71315107

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC C988890 external link Add to cart
PubChem 71315107 external link
Data Source Data ID Price
TRC
C988890 external link Add to cart Please log in.
Data Source Data ID
PubChem 71315107 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Polar Surface Area 104.81 Å2 Rotatable Bonds 22 
Lipinski's Rule of Five false  Acid pKa 13.127856 
H Acceptors H Donor
LogD (pH = 5.5) 1.8924342  LogD (pH = 7.4) 4.2211614 
Log P 5.8516765  Molar Refractivity 158.5901 cm3
Polarizability 62.75373 Å3

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Ethyl Acetate expand Show data source
Methanol expand Show data source
Storage Condition
-20°C Freezer 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 - C988890 external link
A non-immunosuppressive analog of Cyclosporin A.

REFERENCES

REFERENCES

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  • • Twentyman, P. R., et al.: Brit. J. Cancer, 57, 254 (1988)
  • • Twentyman, P. R., et al.: Brit. J. Cancer, 65, 335 (1988)
  • • Schneider, H., et al.: Biochem., 33, 8218 (1994).
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PATENTS

PATENTS

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INTERNET

INTERNET

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