Syringomycin (CHEM029783)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:24:56 UTC
Update Date2016-11-09 01:18:57 UTC
Accession NumberCHEM029783
Identification
Common NameSyringomycin
ClassSmall Molecule
DescriptionProduction by a sugar cane isolate of Pseudomonas syringae pv. syringae Syringomycin is a general name given to a class of lipodepsinonapeptide molecules which are secreted by the plant pathogen Pseudomonas syringae. Lipodepsinonapeptides comprise a closed ring of nine nonribosomally-synthesized amino acids bonded to a fatty acid hydrocarbon tail. A commonly-encountered pathovar (pv) of P. syringae is P. syringae pv syringae which secretes a number of closely-related forms of the molecule. Syringomycins are virulence determinants which means that their secretion is required for the manifestation of disease symptoms on a number of stone fruit crop plants.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SyringomycinMeSH
Chemical FormulaC53H85ClN14O17
Average Molecular Mass1225.790 g/mol
Monoisotopic Mass1224.591 g/mol
CAS Registry Number11140-67-3
IUPAC Name(2S)-2-[(3S,6S,9Z,12S,15S,18S,21R,24R,27S)-18,21-bis(2-aminoethyl)-12-benzyl-15-(3-carbamimidamidopropyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-27-{[(3S)-1,3-dihydroxydodecylidene]amino}-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-24-(hydroxymethyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid
Traditional Name(S)-[(3S,6S,9Z,12S,15S,18S,21R,24R,27S)-18,21-bis(2-aminoethyl)-12-benzyl-15-(3-carbamimidamidopropyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-27-{[(3S)-1,3-dihydroxydodecylidene]amino}-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-24-(hydroxymethyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl](hydroxy)acetic acid
SMILES[H]C(C)=C1N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C(O)[C@]([H])(CCCNC(N)=N)N=C(O)[C@]([H])(CCN)N=C(O)[C@@]([H])(CCN)N=C(O)[C@@]([H])(CO)N=C(O)[C@]([H])(COC(=O)[C@@]([H])(N=C(O)[C@@]([H])(N=C1O)[C@]([H])(O)C(O)=O)[C@]([H])(O)CCl)N=C(O)C[C@@]([H])(O)CCCCCCCCC
InChI IdentifierInChI=1S/C53H85ClN14O17/c1-3-5-6-7-8-9-13-17-30(70)25-39(72)60-37-28-85-52(84)40(38(71)26-54)67-50(81)41(42(73)51(82)83)68-43(74)31(4-2)61-47(78)35(24-29-15-11-10-12-16-29)65-44(75)32(18-14-23-59-53(57)58)62-45(76)33(19-21-55)63-46(77)34(20-22-56)64-48(79)36(27-69)66-49(37)80/h4,10-12,15-16,30,32-38,40-42,69-71,73H,3,5-9,13-14,17-28,55-56H2,1-2H3,(H,60,72)(H,61,78)(H,62,76)(H,63,77)(H,64,79)(H,65,75)(H,66,80)(H,67,81)(H,68,74)(H,82,83)(H4,57,58,59)/b31-4-/t30-,32-,33-,34+,35-,36+,37-,38+,40-,41-,42-/m0/s1
InChI KeyZQVJBRJGDVZANE-MXDMHAPNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Alpha-amino acid ester
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Cyclic carboximidic acid
  • Chlorohydrin
  • Guanidine
  • Carboxylic acid ester
  • Halohydrin
  • Secondary alcohol
  • Amino acid
  • Lactone
  • Amino acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Oxacycle
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Polyol
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Imine
  • Primary alcohol
  • Carbonyl group
  • Primary aliphatic amine
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP0.14ALOGPS
logP-0.43ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.29ChemAxon
pKa (Strongest Basic)11.91ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count30ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area551.77 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity318.36 m³·mol⁻¹ChemAxon
Polarizability124.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-4890000000-a87205c8e8ce8c6b0a61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-4910000001-94876dcce63f1ba43803Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9500000000-7232d7d1d44d6c56bb43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bvi-1920000000-6dbb9a1c3978f7ea4147Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvi-3910000000-883b349674de6078c676Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000001-355721f215f169cf4d70Spectrum
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 IDFDB014712
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSyringomycin E
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11966095
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available