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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:47 UTC
HMDB IDHMDB0014506
Secondary Accession Numbers
  • HMDB14506
Metabolite Identification
Common NameAnidulafungin
DescriptionAnidulafungin, also known as eraxis, 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. Anidulafungin is a drug. Anidulafungin is an extremely weak basic (essentially neutral) compound (based on its pKa). Anidulafungin is a potentially toxic compound.
Structure
Data?1582753187
Synonyms
ValueSource
AnidulafunginaChEBI
AnidulafungineChEBI
AnidulafunginumChEBI
EraxisChEBI
1-((4R,5R)-4,5-Dihydroxy-N2-((4''-(pentyloxy)(1,1':4',1''-terphenyl)-4-yl)carbonyl)-L-ornithine)-echinocandin bMeSH
Chemical FormulaC58H73N7O17
Average Molecular Weight1140.2369
Monoisotopic Molecular Weight1139.506293945
IUPAC NameN-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0⁹,¹³]heptacosan-18-yl]-4-{4-[4-(pentyloxy)phenyl]phenyl}benzamide
Traditional Nameanidulafungin
CAS Registry Number166663-25-8
SMILES
[H][C@@]12C[C@@H](O)CN1C(=O)[C@@]([H])(NC(=O)[C@H](C[C@@H](O)[C@@H](O)NC(=O)[C@]1([H])[C@@H](O)[C@@H](C)CN1C(=O)[C@@]([H])(NC(=O)[C@@]([H])(NC2=O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@@H](C)O)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(OCCCCC)C=C1)[C@@H](C)O
InChI Identifier
InChI=1S/C58H73N7O17/c1-5-6-7-24-82-40-22-18-35(19-23-40)33-10-8-32(9-11-33)34-12-14-37(15-13-34)51(74)59-41-26-43(70)54(77)63-56(79)47-48(71)29(2)27-65(47)58(81)45(31(4)67)61-55(78)46(50(73)49(72)36-16-20-38(68)21-17-36)62-53(76)42-25-39(69)28-64(42)57(80)44(30(3)66)60-52(41)75/h8-23,29-31,39,41-50,54,66-73,77H,5-7,24-28H2,1-4H3,(H,59,74)(H,60,75)(H,61,78)(H,62,76)(H,63,79)/t29-,30+,31+,39+,41-,42-,43+,44-,45-,46-,47-,48-,49-,50-,54+/m0/s1
InChI KeyJHVAMHSQVVQIOT-MFAJLEFUSA-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
  • Para-terphenyl
  • Terphenyl
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Biphenyl
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Phenol ether
  • Phenoxy compound
  • Benzoyl
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Alkanolamine
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.056 g/LNot Available
LogP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP1.87ALOGPS
logP-1.5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area377.42 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity292.29 m³·mol⁻¹ChemAxon
Polarizability122.38 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0900000000-796d08ab3a918780ed58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-2901000001-b967b97492df038b2228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-6940121103-1ffee80492a108a9ab34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0umu-8900000000-f3d09209ecd555a28150Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ftf-9400000005-0db24177f2efbcd59856Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fdx-9120000101-b911329bff55a73c856cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00362 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00362 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 IDDB00362
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID145752
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnidulafungin
METLIN IDNot Available
PubChem Compound166548
PDB IDNot Available
ChEBI ID55346
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vazquez JA: Anidulafungin: a new echinocandin with a novel profile. Clin Ther. 2005 Jun;27(6):657-73. [PubMed:16117974 ]
  2. Vazquez JA, Sobel JD: Anidulafungin: a novel echinocandin. Clin Infect Dis. 2006 Jul 15;43(2):215-22. Epub 2006 Jun 9. [PubMed:16779750 ]
  3. Vazquez JA: The safety of anidulafungin. Expert Opin Drug Saf. 2006 Nov;5(6):751-8. [PubMed:17044802 ]
  4. Cappelletty D, Eiselstein-McKitrick K: The echinocandins. Pharmacotherapy. 2007 Mar;27(3):369-88. [PubMed:17316149 ]
  5. Estes KE, Penzak SR, Calis KA, Walsh TJ: Pharmacology and antifungal properties of anidulafungin, a new echinocandin. Pharmacotherapy. 2009 Jan;29(1):17-30. doi: 10.1592/phco.29.1.17. [PubMed:19113794 ]
  6. Morace G, Borghi E, Iatta R, Montagna MT: Anidulafungin, a new echinocandin: in vitro activity. Drugs. 2009;69 Suppl 1:91-4. doi: 10.2165/11315560-000000000-00000. [PubMed:19877740 ]
  7. Menichetti F: Anidulafungin, a new echinocandin: effectiveness and tolerability. Drugs. 2009;69 Suppl 1:95-7. doi: 10.2165/11315570-000000000-00000. [PubMed:19877741 ]
  8. 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. [PubMed:20606829 ]