(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol

• ChemBase ID: 133733
• Molecular Formular: C20H34O4
• Molecular Mass: 338.48156
• Monoisotopic Mass: 338.24570957
• SMILES: C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]1[C@]32CC[C@@]([C@@H](C1)C3)(CO)O)(C)CO)O
• Canonical SMILES: OC[C@@]1(O)CC[C@]23C[C@@H]1C[C@@H]2CC[C@@H]1[C@]3(C)CC[C@H]([C@@]1(C)CO)O
• InChI: InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
• InChIKey: NOFOAYPPHIUXJR-APNQCZIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.0^1,^1^0.0^2,^7]hexadecane-5,13-diol
• IUPAC Traditional name: aphidicolin
• Synonyms: APC; Aphidicolin from Nigrospora sphaerica; Aphidicolin

Database IDs

• CAS Number: 38966-21-1
• MDL Number: MFCD00083214
• Beilstein Number: 4689958
• PubChem SID: 162228010; 24890452
• PubChem CID: 457964

CALCULATED PROPERTIES

• Acid pKa: 13.633374
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.0900846
• LogD (pH = 7.4): 1.0900843
• Log P: 1.0900846
• Molar Refractivity: 92.3849 cm^3
• Polarizability: 37.137657 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL (stable at least six weeks at -20°C.); ethanol: soluble1 mg/mL (stable at least a week at 4°C.); H2O: insoluble; methanol: soluble10 mg/mL
• Apperance: white powder
• Melting Point: 227-233 °C(lit.)
• Optical Rotation: [α]27/D +12°, c = 1 in methanol(lit.)

Safety Information

• RTECS: PB9185000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... POLA1(5422), POLD1(5424), POLG(5428)

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (TLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C20H34O4

DETAILS

Sigma Aldrich - A0781

Biochem/physiol Actions
Aphidicolin is an antibiotic, a potent antiviral and antimitotic agent and DNA polymerase inhibitor.
Caution
Estimated shelf-life is two years. For optimal stability, it should be protected from light and stored desiccated.

Sigma Aldrich - 10797

Application
Antibiotic isolated from the fungus Nigrospora sphaerica, which is a potent antiviral and antimitotic agent1,2; Inhibitor of DNA polymerase3