(10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one

• ChemBase ID: 153922
• Molecular Formular: C22H22O8
• Molecular Mass: 414.40528
• Monoisotopic Mass: 414.13146766
• SMILES: COc1cc(cc(c1OC)OC)[C@@H]1c2cc3c(cc2[C@@H]([C@@H]2[C@H]1C(=O)OC2)O)OCO3
• Canonical SMILES: COc1cc(cc(c1OC)OC)[C@H]1[C@@H]2C(=O)OC[C@@H]2[C@H](c2c1cc1OCOc1c2)O
• InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1
• InChIKey: YJGVMLPVUAXIQN-HAEOHBJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1,3(7),8-trien-12-one
• IUPAC Traditional name: (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^3,^7.0^1^1,^1^5]hexadeca-1,3(7),8-trien-12-one
• Synonyms: (5R,5aS,8aR,9R)-9-Hydroxy-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; NSC 36407; PPP; Picropodophyllin; Picropodophyllotoxin

Database IDs

• CAS Number: 477-47-4
• MDL Number: MFCD01742647
• PubChem SID: 162248061
• PubChem CID: 72435

CALCULATED PROPERTIES

• Acid pKa: 14.015751
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.6227983
• LogD (pH = 7.4): 1.6227982
• Log P: 1.6227983
• Molar Refractivity: 103.905 cm^3
• Polarizability: 41.000076 Å^3
• Polar Surface Area: 92.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: white powder

Safety Information

• RTECS: LV2510000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 21-25-36/37/38-68
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C22H22O8

DETAILS

Sigma Aldrich - T9576

Biochem/physiol Actions
Picropodophyllotoxin is an insulin-like growth factor-I (IGF-I) receptor kinase inhibitor.
Quality
May contain 2-3% ethanol (w/w)