(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

• ChemBase ID: 126882
• Molecular Formular: C23H22O6
• Molecular Mass: 394.41718
• Monoisotopic Mass: 394.14163842
• SMILES: O=C1c2c(O[C@@H]3COc4cc(OC)c(OC)cc4[C@H]13)c1C=CC(Oc1cc2)(C)C
• Canonical SMILES: COc1cc2c(cc1OC)OC[C@@H]1[C@H]2C(=O)c2c(O1)c1C=CC(Oc1cc2)(C)C
• InChI: InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1
• InChIKey: ORDAZKGHSNRHTD-UXHICEINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^3,^1^2.0^4,^9.0^1^5,^2^0]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one; (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^3,^1^2.0^4,^9.0^1^5,^2^0]docosa-3,5,9,11,15,17,19-heptaen-13-one
• IUPAC Traditional name: deguelin; (1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0^3,^1^2.0^4,^9.0^1^5,^2^0]docosa-3,5,9,11,15,17,19-heptaen-13-one
• Synonyms: 3H-Bis(1)benzopyrano; (3,4-b:6',5'-e)pyran-7(7aH)-one; 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7aS,13aS)-; 3H-Bis(1); benzopyrano(3,4-b:6',5'-e)pyran-7(7aH)-one; 13,13a-dihydro- 9,10-dimethoxy-3,3-dimethyl-, (7aS-cis)-; Deguelin; (7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one; (-)-Deguelin; Deguelin

Database IDs

• CAS Number: 522-17-8
• MDL Number: MFCD01740600
• PubChem SID: 162221208
• PubChem CID: 107935
• CHEMBL: 393417
• Chemspider ID: 97058
• Wikipedia Title: Deguelin

CALCULATED PROPERTIES

• Acid pKa: 11.72448
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.3042057
• LogD (pH = 7.4): 3.3041852
• Log P: 3.304206
• Molar Refractivity: 107.218 cm^3
• Polarizability: 41.272274 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: Powder; white to yellow solid
• Melting Point: 171°C; 85-87 °C(lit.)

Safety Information

• RTECS: DX1500000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C23H22O6

DETAILS

Sigma Aldrich - D0817

Biochem/physiol Actions
Inhibitor of activated Akt. Does not affect MAPK, ERK1/2, or JNK. Anticancer, chemoprotective agent.