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

• ChemBase ID: 72823
• Molecular Formular: C47H75NO17
• Molecular Mass: 926.0949
• Monoisotopic Mass: 925.50349995
• SMILES: [C@@H]1([C@H](C)[C@@H]([C@H](/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@@H](C[C@@H]2O[C@](C[C@@H](O)[C@@H](CC[C@@H](O)C[C@@H](O)C[C@@H](O)CC(=O)O1)O)(C[C@@H]([C@H]2C(=O)O)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@]2(O)C[C@H](O)[C@H]([C@@H](O2)C[C@H](/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@@H]([C@H]([C@H]([C@@H](OC(=O)C[C@@H](C[C@@H](C1)O)O)C)C)O)C)OC1O[C@@H](C)[C@@H]([C@H]([C@H]1O)N)O)C(=O)O
• InChI: InChI=1S/C47H75NO17/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)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,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: VQOXZBDYSJBXMA-CCBILCGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(3R,4R,5R,6S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• IUPAC Traditional name: (1S,3R,4R,7R,9R,11R,15S,16R,17R,18S,19E,21E,25E,27E,29E,31E,33R,35S,36R,37S)-33-{[(3R,4R,5R,6S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-1,3,4,7,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,25,27,29,31-hexaene-36-carboxylic acid
• Synonyms: Bio-Statin; Mycostatin Pastilles; Nystatin

Database IDs

• CAS Number: 1400-61-9
• PubChem SID: 162037744
• PubChem CID: 71299255

CALCULATED PROPERTIES

• Acid pKa: 3.611593
• H Acceptors: 17
• H Donor: 12
• LogD (pH = 5.5): -1.9412671
• LogD (pH = 7.4): -1.9444739
• Log P: -1.9383262
• Molar Refractivity: 243.5539 cm^3
• Polarizability: 94.91027 Å^3
• Polar Surface Area: 319.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1934

Research Area: Infection
Biological Activity:
Nystatin (Mycostatin) is a polyene antifungal drug to which many molds and yeasts are sensitive, including Candida spp. Nystatin has some toxicity associated with it when given intravenously, but it is not absorbed across intact skin or mucous membranes. It is considered a relatively safe drug for treating oral or gastrointestinal fungal infections. Nystatin interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. [1]

REFERENCES

• http://www.drugbank.ca/drugs/DB00646