(3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid

• ChemBase ID: 134017
• Molecular Formular: C21H39NO6
• Molecular Mass: 401.53746
• Monoisotopic Mass: 401.27773797
• SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H](C(CO)(C(=O)O)N)O)O
• Canonical SMILES: CCCCCCC(=O)CCCCCC/C=C/C[C@H]([C@@H](C(C(=O)O)(CO)N)O)O
• InChI: InChI=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
• InChIKey: ZZIKIHCNFWXKDY-GNTQXERDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid; (2S,3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
• IUPAC Traditional name: (3R,4R,6E)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid; myriocin
• Synonyms: [2S-(2R*,3S*,4S*,6E)]-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic Acid; (+)-Myriocin; NSC 177379; (2S,3R,4R)-(E)-2-Amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic Acid; Myriocin; (2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-eicosenoic acid; ISP-I; Thermozymocidin; Myriocin from Mycelia sterilia

Database IDs

• CAS Number: 35891-70-4
• MDL Number: MFCD01632772
• PubChem SID: 162228294; 24896622
• PubChem CID: 6438394

CALCULATED PROPERTIES

• Acid pKa: 2.0621011
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.4919639
• LogD (pH = 7.4): 0.44911402
• Log P: 0.4920756
• Molar Refractivity: 109.3753 cm^3
• Polarizability: 43.162376 Å^3
• Polar Surface Area: 141.08 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble2 mg/mL
• Apperance: off-white powder

Safety Information

• RTECS: JX3890000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - M1177

Biochem/physiol Actions
Fungal metabolite with potent immunosuppressant activity. Inhibits serine palmitoyltransferase at picomolar concentrations blocking synthesis of ceramide, a precursor of sphingomyelin and glycosphingolipids. Disrupts substratum adhesion of melanoma cells. It has been suggested that its immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction.

Toronto Research Chemicals - M884400

Myriocin is a atypical amino acid and an antibiotic with potent immunosuppressant activity. Studies suggest that the immunosuppressant activity in the cytotoxic T-cell line CTTL-2 is due to apoptosis induction. Myriocin very potent inhibitor of serine pal

REFERENCES

• Miyake, Y., et al.: Biochem. Biophys. Res. Commun., 211, 396 (1995)
• Hidari, K.I.P.J. et al.: J. Biol. Chem., 271, 14636 (1995)
• Nakamura, S. et al.: J. Biol. Chem., 271, 1255 (1995)
• De Zélicourt, A. et al.: Planta 230, 1047 (1995)