(2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 157884
• Molecular Formular: C41H68O14
• Molecular Mass: 784.97022
• Monoisotopic Mass: 784.46090686
• SMILES: C[C@]12CC[C@@]34C[C@]53CC[C@@H](C([C@@H]5[C@H](C[C@H]4[C@@]1(C[C@@H]([C@@H]2[C@]1(CC[C@H](O1)C(C)(C)O)C)O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)(C)C)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@]4([C@@]5([C@@H]2C(C)(C)[C@H](CC5)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)C4)CC[C@]2([C@@]3(C)C[C@@H]([C@@H]2[C@@]2(C)CC[C@H](O2)C(O)(C)C)O)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C41H68O14/c1-35(2)24(54-33-29(48)26(45)20(44)17-51-33)9-11-41-18-40(41)13-12-37(5)31(39(7)10-8-25(55-39)36(3,4)50)19(43)15-38(37,6)23(40)14-21(32(35)41)52-34-30(49)28(47)27(46)22(16-42)53-34/h19-34,42-50H,8-18H2,1-7H3/t19-,20+,21-,22+,23-,24-,25-,26-,27+,28-,29+,30+,31-,32-,33-,34+,37+,38-,39+,40-,41+/m0/s1
• InChIKey: QMNWISYXSJWHRY-YLNUDOOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.0^1,^3.0^3,^8.0^1^2,^1^6]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5S,6R)-2-{[(1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-14-hydroxy-15-[(2R,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}pentacyclo[9.7.0.0^1,^3.0^3,^8.0^1^2,^1^6]octadecan-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Astragaloside IV; 黄芪甲苷 IV

Database IDs

• CAS Number: 84687-43-4
• MDL Number: MFCD16036240
• PubChem SID: 162252020
• PubChem CID: 13943297

CALCULATED PROPERTIES

• Acid pKa: 11.925284
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -0.3115432
• LogD (pH = 7.4): -0.31155598
• Log P: -0.31154302
• Molar Refractivity: 194.5801 cm^3
• Polarizability: 79.65742 Å^3
• Polar Surface Area: 228.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 295-296 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: >98.0%; ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C41H68O14

DETAILS

Sigma Aldrich - 74777

Biochem/physiol Actions
Anti-inflammatory.
Other Notes
Chemical constituent of Astragali radix1,2