Amphotericin B (CED0001054)

Record Information
Version1.0
Creation Date2016-05-22 03:37:10 UTC
Update Date2026-05-14 16:45:55 UTC
Accession NumberCHEM016564
Identification
Common NameAmphotericin B
ClassSmall Molecule
Description
Amphotericin B is a compound with the chemical formula C47H73NO17. Amphotericin B belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. With an average molecular weight of 924.09 g/mol, Amphotericin B is a heavy molecule. This substance is found in or released from 17 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics, antimycotics, gynecologicals, intestinal antiinfectives, and stomatological preparations. In the realm of household cleaning and consumer products, it is linked to soap detergents, bleaching agents, tobacco pipes, tobacco smoke filters, and non electric simulated smoking devices. Additionally, it is identified in electrical and electronic equipment, including antennas, amplifiers, hybrid capacitors, electrically stimulated smoking devices, and electric hearing aids, among two other sources. Recorded exposure routes for this compound include oral, intravenous, and inhalation.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,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-carboxylateGenerator
AmphotericinMeSH
Amphotericin b colloidal dispersionMeSH
AmphocilMeSH
Amphotericin b cholesterol dispersionMeSH
FungizoneMeSH
Chemical FormulaC47H73NO17
Average Molecular Mass924.091 g/mol
Monoisotopic Mass923.488 g/mol
CAS Registry Number1397-89-3
IUPAC Name(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,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-carboxylic acid
Traditional Nameamphotericin B
SMILES[H][C@]1(O)C[C@@]2(O)C[C@@]([H])(O)C[C@@]([H])(O)[C@]([H])(O)CC[C@@]([H])(O)C[C@@]([H])(O)CC(=O)O[C@@]([H])(C)[C@]([H])(C)[C@]([H])(O)[C@@]([H])(C)C=CC=CC=CC=CC=CC=CC=C[C@@]([H])(C[C@]([H])(O2)[C@]1([H])C(O)=O)O[C@]1([H])O[C@]([H])(C)[C@@]([H])(O)[C@]([H])(N)[C@]1([H])O
InChI IdentifierInChI=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)/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
InChI KeyAPKFDSVGJQXUKY-KKGHZKTASA-N
Chemical Taxonomy
Description 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
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • 1,2-aminoalcohol
  • Hemiacetal
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.082 g/LALOGPS
logP-0.66ALOGPS
logP-2.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area319.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity244.67 m³·mol⁻¹ChemAxon
Polarizability101.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0000000696-af354c0714b1f3055896Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000000920-e259a6945873d29a3864Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1000000900-2098546b5e33eaee0aebNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0nvr-2000000395-7e8ba184739a29a08068Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w4i-0000000590-bd4e765e6de78bc09304Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2000002900-e34b699106d23f4b3f80Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
241Stomatological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
254Intestinal antiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
348AntimycoticsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureATP synthase subunit beta, mitochondrialP00830Saccharomyces cerevisiae S288cPredicted (SEA)0.389246
DIS3-like exonuclease 2 structureClick to view 3D structureDIS3-like exonuclease 2Q8IYB7HumansPredicted (SEA)0.934191
DNA topoisomerase 2-alpha structureClick to view 3D structureDNA topoisomerase 2-alphaP11388HumansPredicted (SEA)52.8596
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)2104.5
V-type proton ATPase subunit S1 structureClick to view 3D structureV-type proton ATPase subunit S1Q15904HumansPredicted (SEA)0.389246
Click to view 3D structureThreonyl-tRNA synthaseG3FIN0Phytophthora sojaePredicted (SEA)0.233548
Click to view 3D structureE-selectinP98105Rattus norvegicusPredicted (SEA)4.82665
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP51639Rattus norvegicusPredicted (SEA)95.2096
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)1192.42
3-hydroxy-3-methylglutaryl-coenzyme A reductase structureClick to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP04035HumansPredicted (SEA)220.625
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)5272.57
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1P54751Mus musculusPredicted (SEA)10.7432
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)7478.74
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)5423.52
Gap junction beta-2 protein structureClick to view 3D structureGap junction beta-2 proteinP29033HumansPredicted (SEA)12.4559
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)3608.86
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)7567.02
Signal transducer and activator of transcription 3 structureClick to view 3D structureSignal transducer and activator of transcription 3P40763HumansPredicted (SEA)4067.47
Click to view 3D structurePeptidyl-prolyl cis-trans isomerase FKBP1AP26883Mus musculusPredicted (SEA)2.49118
Click to view 3D structureNeurogenic locus notch homolog protein 1Q01705Mus musculusPredicted (SEA)16.8933
Gap junction alpha-1 protein structureClick to view 3D structureGap junction alpha-1 proteinP17302HumansPredicted (SEA)15.6477
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)5995.32
Click to view 3D structureMotilin receptorA5A4K8Oryctolagus cuniculusPredicted (SEA)1.47914
Click to view 3D structureInositol monophosphatase 1P20456Bos taurusPredicted (SEA)171.19
Peptidyl-prolyl cis-trans isomerase FKBP1A structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase FKBP1AP62942HumansPredicted (SEA)952.174
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID14956
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References