Daptomycin (CHEM044231)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:54:08 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044231
Identification
Common NameDaptomycin
ClassSmall Molecule
Description
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DeptomycinMeSH
Daptomycin, 9-L beta-aspartic acidMeSH
CubicinMeSH
Daptomycin, 9 L beta aspartic acidMeSH
Chemical FormulaC72H101N17O26
Average Molecular Mass1620.693 g/mol
Monoisotopic Mass1619.710 g/mol
CAS Registry Number103060-53-3
IUPAC Name(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-(1-carboxypropan-2-yl)-5,8,11,14,17,20,23,26,29-nonahydroxy-9-(hydroxymethyl)-18,31-dimethyl-2-oxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriaconta-4,7,10,13,16,19,22,25,28-nonaen-30-yl]-C-hydroxycarbonimidoyl}-3-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-[(1-hydroxydecylidene)amino]-3-(1H-indol-3-yl)propylidene]amino}-3-(C-hydroxycarbonimidoyl)propylidene]amino}propanoic acid
Traditional Name(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-(1-carboxypropan-2-yl)-5,8,11,14,17,20,23,26,29-nonahydroxy-9-(hydroxymethyl)-18,31-dimethyl-2-oxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriaconta-4,7,10,13,16,19,22,25,28-nonaen-30-yl]-C-hydroxycarbonimidoyl}-3-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-[(1-hydroxydecylidene)amino]-3-(1H-indol-3-yl)propylidene]amino}-3-(C-hydroxycarbonimidoyl)propylidene]amino}propanoic acid
SMILES[H]C(C)(CC(O)=O)[C@]1([H])N=C(O)[C@@]([H])(CO)N=C(O)CN=C(O)[C@]([H])(CC(O)=O)N=C(O)[C@@]([H])(C)N=C(O)[C@]([H])(CC(O)=O)N=C(O)[C@]([H])(CCCN)N=C(O)CN=C(O)C([H])(N=C(O)[C@]([H])(CC(O)=O)N=C(O)[C@]([H])(CC(O)=N)N=C(O)[C@]([H])(CC2=CNC3=CC=CC=C23)N=C(O)CCCCCCCCC)C([H])(C)OC(=O)[C@]([H])(CC(=O)C2=CC=CC=C2N)N=C1O
InChI IdentifierInChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35?,36-,37?,43+,44+,45+,46+,47+,48+,49+,50-,60+,61?/m1/s1
InChI KeyDOAKLVKFURWEDJ-OFNKPWESSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as primary carboxylic acid amides. Primary carboxylic acid amides are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentPrimary carboxylic acid amides
Alternative Parents
Substituents
  • Primary carboxylic acid amide
  • Alkyl chloride
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl iodide
  • Alkyl halide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP0.93ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count23ChemAxon
Polar Surface Area748.38 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity411.28 m³·mol⁻¹ChemAxon
Polarizability159.74 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uei-0000195000-d307278a65d07c4ef2b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0itc-2612291000-e40ed1a6d6520710f0d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mi-5914111000-d12a04754b89ad30031cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fk9-0000094000-82873a0f8cc1583d67caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ukc-1100194000-19118807733955c744b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-9622320000-d6bf995b65794136005fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 ID16129629
Kegg Compound IDC12013
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available