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1397-89-3 molecular structure
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(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(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-carboxylic acid

ChemBase ID: 72773
Molecular Formular: C47H73NO17
Molecular Mass: 924.07902
Monoisotopic Mass: 923.48784988
SMILES and InChIs

SMILES:
[C@@H]1([C@H](C)[C@@H]([C@H](/C=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)O1)O)O)O)O)O)(O2)O)O)C(=O)O)OC1[C@H]([C@H]([C@@H]([C@H](O1)C)O)N)O)C)O)C
Canonical SMILES:
O[C@@H]1CC[C@@H](O)[C@H](O)C[C@H](O)C[C@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C1)O)C)C)O)C)OC1O[C@H](C)[C@H]([C@@H]([C@@H]1O)N)O)C(=O)O
InChI:
InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46?,47+/m0/s1
InChIKey:
APKFDSVGJQXUKY-QSSPICSASA-N

Cite this record

CBID:72773 http://www.chembase.cn/molecule-72773.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(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-carboxylic acid
IUPAC Traditional name
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(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-carboxylic acid
Synonyms
Amphotericin B
Fungilin
Fungizone
AmBisome
Fungisome
CAS Number
1397-89-3
PubChem SID
162037694
PubChem CID
9919339

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S1636 external link Add to cart Please log in.
Data Source Data ID
PubChem 9919339 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors 17  H Donor 12 
LogD (pH = 5.5) -2.3028812  LogD (pH = 7.4) -2.3064086 
Log P -2.3001616  Molar Refractivity 244.6705 cm3
Polarizability 94.662575 Å3 Polar Surface Area 319.61 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Acid pKa 3.5797393 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals
Selleck Chemicals - S1636 external link
Research Area: Infection
Biological Activity:
Amphotericin B is a polyene, antifungal antibiotic produced from a strain of Streptomyces nodosus. (IC50=0.028–0.290 μg/ml) [1] It has been the most effective systemic antifungal agent. [2] For Histoplasma and Blastomyces infections the mean effective dose (ED50) of amphotericin B was 0.3 mg/kg, whereas the corresponding values for AME, respectively, were 2.4 and 2.8 mg/kg. For Cryptococcus infection the ED50 for amphotericin B was 0.2 mg/kg compared with 2.0 mg/kg for AME. The ED50 of amphotericin B for Candida infection was lower than 0.05 mg/kg and the value of AME was between 0.5 to 0.05 mg/kg. [3]

REFERENCES

REFERENCES

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  • • Kayser O et al. Acta Trop. 2003 Apr;86(1):105-7.
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PATENTS

PATENTS

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INTERNET

INTERNET

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