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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2019-01-11 19:34:19 UTC
HMDB IDHMDB0014784
Secondary Accession Numbers
  • HMDB14784
Metabolite Identification
Common NameNystatin
DescriptionNystatin 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.
Structure
Data?1547235259
Synonyms
ValueSource
MycostatinChEBI
Chemical FormulaC47H75NO17
Average Molecular Weight926.0949
Monoisotopic Molecular Weight925.503499979
IUPAC Name(21E,23E,25E,27E,31E,33E)-20-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,8,11,12,16,18,36-octahydroxy-35,37,38-trimethyl-2,14-dioxo-1-oxacyclooctatriaconta-21,23,25,27,31,33-hexaene-17-carboxylic acid
Traditional Namenystatin
CAS Registry Number1400-61-9
SMILES
C[C@H]1OC(OC2CC(O)C(C(O)CC(=O)CC(O)C(O)CCC(O)CC(O)CC(O)CC(=O)OC(C)C(C)C(O)C(C)\C=C\C=C\CC\C=C\C=C\C=C\C=C\2)C(O)=O)[C@@H](O)[C@@H](N)[C@@H]1O
InChI Identifier
InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-35(65-47-45(60)42(48)44(59)30(4)64-47)26-39(56)41(46(61)62)38(55)24-34(52)23-37(54)36(53)20-19-31(49)21-32(50)22-33(51)25-40(57)63-29(3)28(2)43(27)58/h5-6,8,10-18,27-33,35-39,41-45,47,49-51,53-56,58-60H,7,9,19-26,48H2,1-4H3,(H,61,62)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27?,28?,29?,30-,31?,32?,33?,35?,36?,37?,38?,39?,41?,42+,43?,44-,45+,47?/m1/s1
InChI KeyZDFDJJJGIRGMBE-AFARJNEBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Amino acid
  • Ketone
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point160 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.066 g/LNot Available
LogP0.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP-2.8ALOGPS
logP-2.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.62ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area327.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity245.18 m³·mol⁻¹ChemAxon
Polarizability102.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0000000696-2dbe48a763da2c51ff0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0010000922-aa0997aef4cbe4d08c7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1002103911-eae0bbc46987f1df1bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08g0-2000000496-774431ed75efe06401c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ir-0000000490-8f81c2a4e4a2977923e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1000000900-94ba1a7b1c2cf5359defView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00646 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00646 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00646
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10128183
KEGG Compound IDC06572
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNystatin
METLIN IDNot Available
PubChem Compound11953884
PDB IDNot Available
ChEBI ID7660
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Akaike N, Harata N: Nystatin perforated patch recording and its applications to analyses of intracellular mechanisms. Jpn J Physiol. 1994;44(5):433-73. [PubMed:7534361 ]