12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.03,8.08,25]heptacosane]-4',18',20'-triene-11',17',22'-trione

• ChemBase ID: 155465
• Molecular Formular: C27H34O9
• Molecular Mass: 502.55346
• Monoisotopic Mass: 502.22028267
• SMILES: CC1CCOC(=O)/C=C/C=C/C(=O)OC2CC3C4(C2(C2(CCC(=CC2O3)C)COC(=O)C1O)C)CO4
• Canonical SMILES: O=C1/C=C/C=C/C(=O)OCCC(C(C(=O)OCC23C4(C(O1)CC(C14CO1)OC3C=C(CC2)C)C)O)C
• InChI: InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3
• InChIKey: NLUGUZJQJYVUHS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^3,^8.0^8,^2^5]heptacosane]-4',18',20'-triene-11',17',22'-trione
• IUPAC Traditional name: 12'-hydroxy-5',13',25'-trimethyl-2',10',16',23'-tetraoxaspiro[oxirane-2,26'-tetracyclo[22.2.1.0^3,^8.0^8,^2^5]heptacosane]-4',18',20'-triene-11',17',22'-trione
• Synonyms: Muconomycin A; Verrucarin A from Myrothecium sp.

Database IDs

• CAS Number: 3148-09-2
• MDL Number: MFCD00056759
• PubChem SID: 162249603; 24900750
• PubChem CID: 57517202

CALCULATED PROPERTIES

• Acid pKa: 12.477668
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.5549805
• LogD (pH = 7.4): 2.554977
• Log P: 2.5549805
• Molar Refractivity: 128.5137 cm^3
• Polarizability: 50.50024 Å^3
• Polar Surface Area: 120.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: WH1314900
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C27H34O9

DETAILS

Sigma Aldrich - V4877

Biochem/physiol Actions
Verrucarin A is phytotoxic to plantlet cultures and cytotoxic to cultured mammalian cell lines.
Other Notes
Macrocyclic trichothecene mycotoxin.