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36148-89-7 molecular structure
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methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate

ChemBase ID: 160589
Molecular Formular: C48H75NO17
Molecular Mass: 938.1056
Monoisotopic Mass: 937.50349995
SMILES and InChIs

SMILES:
C\1=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]([C@H]1C)O)C)C)O)O)O)O)O)(O)O2)O)C(=O)OC)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)C)O)N)O
Canonical SMILES:
COC(=O)[C@H]1[C@@H]2C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@H]([C@H]([C@@H](OC(=O)C[C@@H](C[C@@H](CC[C@H]([C@@H](C[C@@H](C[C@@](O2)(C[C@@H]1O)O)O)O)O)O)O)C)C)O)O[C@@H]1O[C@H](C)[C@H]([C@H]([C@@H]1O)N)O
InChI:
InChI=1S/C48H75NO17/c1-28-18-16-14-12-10-8-6-7-9-11-13-15-17-19-35(65-47-45(59)42(49)44(58)31(4)64-47)25-39-41(46(60)62-5)38(55)27-48(61,66-39)26-34(52)23-37(54)36(53)21-20-32(50)22-33(51)24-40(56)63-30(3)29(2)43(28)57/h6-19,28-39,41-45,47,50-55,57-59,61H,20-27,49H2,1-5H3/b7-6+,10-8+,11-9+,14-12+,15-13+,18-16+,19-17+/t28-,29-,30-,31+,32+,33+,34-,35-,36+,37+,38-,39?,41+,42-,43+,44+,45-,47-,48+/m0/s1
InChIKey:
UAZIZEMIKKIBCA-SROBOZQESA-N

Cite this record

CBID:160589 http://www.chembase.cn/molecule-160589.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
IUPAC Traditional name
amphotericin B methyl ester
Synonyms
Amphotericin B Monomethyl Ester
Amphotericin B Methyl Ester 90%
CAS Number
36148-89-7
PubChem SID
162254724
PubChem CID
11968030

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
TRC A634255 external link Add to cart
PubChem 11968030 external link
Data Source Data ID Price
TRC
A634255 external link Add to cart Please log in.
Data Source Data ID
PubChem 11968030 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.823185  H Acceptors 16 
H Donor 11  LogD (pH = 5.5) -2.8226233 
LogD (pH = 7.4) -1.5940475  Log P 0.1097699 
Molar Refractivity 249.4396 cm3 Polarizability 96.73872 Å3
Polar Surface Area 308.61 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Methanol expand Show data source
Apperance
Yellow Solid expand Show data source
Melting Point
>175°C (dec.) expand Show data source
Storage Condition
-20°C Freezer 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 - A634255 external link
Amphotericin B Methyl Ester is the methyl ester derivative of the polyene antibiotic Amphotericin B (A634250). Amphotericin B Methyl Esterin is a cholesterol binding compound that showed inhibiton of human immunodeficiency virus type 1 (HIV-1).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Waheed, A.A. et al.: J. Biol. Chem., 281, 28699 (2006)
  • • Waheed, A. et al.: J. Virol., 82, 9776 (2006)
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PATENTS

PATENTS

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INTERNET

INTERNET

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