Myriocin (CHEM018943)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:41:17 UTC
Update Date2016-11-09 01:15:54 UTC
Accession NumberCHEM018943
Identification
Common NameMyriocin
ClassSmall Molecule
DescriptionAn amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Antibiotic isp-IChEBI
ThermozymocidinChEBI
ISP-1Kegg
ISP-1 serine palmitoyltransferase inhibitorMeSH
2-Amino-2-hydroxymethyl-3,4-dihydroxy-14- oxoeicos-6-enoic acidMeSH
SPI-1 inhibitorMeSH
ISP-1 suppressantMeSH
(e,2S,3R,4R)-2-amino-3,4-Dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoateGenerator
MyriocinMeSH
Chemical FormulaC21H39NO6
Average Molecular Mass401.544 g/mol
Monoisotopic Mass401.278 g/mol
CAS Registry Number35891-70-4
IUPAC Name(2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
Traditional Namemyriocin
SMILES[H]\C(CCCCCCC(=O)CCCCCC)=C(\[H])C[C@@]([H])(O)[C@]([H])(O)[C@@](N)(CO)C(O)=O
InChI IdentifierInChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1
InChI KeyZZIKIHCNFWXKDY-GNTQXERDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • D-alpha-amino acid
  • L-alpha-amino acid
  • Amino fatty acid
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Unsaturated fatty acid
  • Hydroxy acid
  • 1,3-aminoalcohol
  • Amino acid
  • Secondary alcohol
  • Amino acid or derivatives
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary aliphatic amine
  • Organic oxide
  • Primary amine
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • 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 Solubility0.062 g/LALOGPS
logP0.3ALOGPS
logP0.49ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)8.35ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area141.08 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity109.38 m³·mol⁻¹ChemAxon
Polarizability46.65 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-2209100000-24d20694829459488130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-9422000000-2bf0cd7171010c3d55efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-9520000000-2bf68838a1dd107b168fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2319500000-7ba3ca68f1c00ef0525cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052s-7669000000-9dc7800238eaf83d7439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9400000000-d179258d6a789d25961aSpectrum
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 IDC00016936
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMyriocin
Chemspider IDNot Available
ChEBI ID582124
PubChem Compound ID6438394
Kegg Compound IDC19914
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15679316
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21456524
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23178537
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23659342
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23802886
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23957439
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24141140
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24395529
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24456332