Micafungin (CED0003277)

Record Information
Version1.0
Creation Date2016-05-25 18:25:21 UTC
Update Date2026-05-14 16:58:10 UTC
Accession NumberCHEM022244
Identification
Common NameMicafungin
ClassSmall Molecule
Description
Micafungin is a compound with the chemical formula C56H71N9O23S. Micafungin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 1,270 g/mol, Micafungin is a heavy molecule. The compound is found in or released from two recorded sources: antennas in electrical and electronic equipment and antimycotics in healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this substance is intravenous. Micafungin acts upon two recorded protein targets, serving as an inhibitor or modulator of 1,3-beta-glucan synthase component GSC2 and 1,3-beta-glucan synthase component FKS1 (fksA).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MycamineChEBI
FK-463HMDB
Micafungin sodiumHMDB
Chemical FormulaC56H71N9O23S
Average Molecular Mass1270.274 g/mol
Monoisotopic Mass1269.438 g/mol
CAS Registry Number235114-32-6
IUPAC Name{5-[(1S,2S)-2-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-3-[(1R)-2-carbamoyl-1-hydroxyethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-18-(4-{5-[4-(pentyloxy)phenyl]-1,2-oxazol-3-yl}benzamido)-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0⁹,¹³]heptacosan-6-yl]-1,2-dihydroxyethyl]-2-hydroxyphenyl}oxidanesulfonic acid
Traditional Namemicafungin
SMILESCCCCCOC1=CC=C(C=C1)C1=CC(=NO1)C1=CC=C(C=C1)C(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)C1=CC(OS(O)(=O)=O)=C(O)C=C1)[C@H](O)CC(N)=O
InChI IdentifierInChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1
InChI KeyPIEUQSKUWLMALL-YABMTYFHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Cyclic alpha peptide
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Phenylsulfate
  • Alpha-amino acid or derivatives
  • Arylsulfate
  • Benzamide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Heteroaromatic compound
  • Isoxazole
  • Organic sulfuric acid or derivatives
  • Azole
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Primary carboxylic acid amide
  • Lactam
  • Ether
  • Azacycle
  • Oxacycle
  • Alkanolamine
  • Organoheterocyclic compound
  • Polyol
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.22 g/LALOGPS
logP0.67ALOGPS
logP-6.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area510.14 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity303.07 m³·mol⁻¹ChemAxon
Polarizability128.22 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0090000000-4b64f397b40e9008eeddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2291000000-4aa58ad76a6198021e14Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00e9-9453000001-3dc99a3a598f50ee7ca2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fsi-0590000000-af7cc7a7d3742e6e3151Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-6970000000-2b09e28866be1a89cf60Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-015l-8940000003-178cb82ef6ea2cf80947Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0090000000-1a19fd3d6300f9b33adbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kmi-1196000000-f2edf39e533b563fa71aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fdo-8921000008-d7d7832ba7a2829ff46aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-734ebe6b07172472a082Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-4690000001-fa2fc98848c5526a3370Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9230000001-ae99dc8d18ace78fb005Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot 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
348AntimycoticsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
2 pathways
Micafungin Action Pathway
Micafungin Action Pathway
Micafungin Drug Metabolism Action Pathway
Micafungin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-1,3-glucan synthaseO13383Candida albicansPredicted (SEA)0.233548
Click to view 3D structure1,3-beta-glucan synthaseF5BCZ9Candida glabrataPredicted (SEA)0.622794
Click to view 3D structure1,3-beta-glucan synthase component GSC2P40989Baker's yeastPredicted (SEA)0.700643
Click to view 3D structureBeta-1,3-glucan synthaseO13428Candida albicansPredicted (SEA)2.72472
Click to view 3D structureKallikrein 1-related peptidase b5P15945Mus musculusPredicted (SEA)87.7361
Gamma-aminobutyric acid receptor subunit beta-1 structureClick to view 3D structureGamma-aminobutyric acid receptor subunit beta-1P18505HumansPredicted (SEA)88.7481
Kallikrein-5 structureClick to view 3D structureKallikrein-5Q9Y337HumansPredicted (SEA)406.606
Tumor necrosis factor receptor superfamily member 9 structureClick to view 3D structureTumor necrosis factor receptor superfamily member 9Q07011HumansPredicted (SEA)86.8797
Albumin structureClick to view 3D structureAlbuminP02768HumansPredicted (SEA)684.139
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)2836.2
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)1260.61
Neutral ceramidase structureClick to view 3D structureNeutral ceramidaseQ9NR71HumansPredicted (SEA)148.926
Signal peptidase I structureClick to view 3D structureSignal peptidase IP00803Escherichia coli (strain K12)Predicted (SEA)22.3427
Lymphocyte activation gene 3 protein structureClick to view 3D structureLymphocyte activation gene 3 proteinP18627HumansPredicted (SEA)82.4423
Click to view 3D structureIntegrin alpha-3P26006HumansPredicted (SEA)45.0747
Kallikrein-7 structureClick to view 3D structureKallikrein-7P49862HumansPredicted (SEA)411.822
Myeloblastin structureClick to view 3D structureMyeloblastinP24158HumansPredicted (SEA)127.517
Click to view 3D structureCCN family member 2P29279HumansPredicted (SEA)184.113
Nectin-4 structureClick to view 3D structureNectin-4Q96NY8HumansPredicted (SEA)91.6285
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)4876.94
von Hippel-Lindau disease tumor suppressor structureClick to view 3D structurevon Hippel-Lindau disease tumor suppressorP40337HumansPredicted (SEA)76.0587
Click to view 3D structureEndothelin-1 receptorP21450Bos taurusPredicted (SEA)221.715
Peptidyl-prolyl cis-trans isomerase C structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase CP45877HumansPredicted (SEA)18.2167
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)1544.68
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)3789.54
Concentrations
Not Available
External Links
DrugBank IDDB01141
HMDB IDHMDB0015272
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMicafungin
Chemspider ID419105
ChEBI ID600520
PubChem Compound ID477468
Kegg Compound IDC15819
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Groll AH, Stergiopoulou T, Roilides E, Walsh TJ: Micafungin: pharmacology, experimental therapeutics and clinical applications. Expert Opin Investig Drugs. 2005 Apr;14(4):489-509.
2. Chandrasekar PH, Sobel JD: Micafungin: a new echinocandin. Clin Infect Dis. 2006 Apr 15;42(8):1171-8. Epub 2006 Mar 14.
3. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703.
4. Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20.
5. Ikeda F, Tanaka S, Ohki H, Matsumoto S, Maki K, Katashima M, Barrett D, Aoki Y: Role of micafungin in the antifungal armamentarium. Curr Med Chem. 2007;14(11):1263-75.
6. Wiederhold NP, Lewis JS 2nd: The echinocandin micafungin: a review of the pharmacology, spectrum of activity, clinical efficacy and safety. Expert Opin Pharmacother. 2007 Jun;8(8):1155-66.
7. Vehreschild JJ, Cornely OA: Micafungin sodium, the second of the echinocandin class of antifungals: theory and practice. Future Microbiol. 2006 Aug;1(2):161-70.
8. Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1.
9. Bormann AM, Morrison VA: Review of the pharmacology and clinical studies of micafungin. Drug Des Devel Ther. 2009 Dec 29;3:295-302.
10. Grover ND: Echinocandins: A ray of hope in antifungal drug therapy. Indian J Pharmacol. 2010 Feb;42(1):9-11. doi: 10.4103/0253-7613.62396.
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17194830
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17307974
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17325217
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17325225
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17420211
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=17785512