(2R)-3-[(2R,5S,6S,8R)-8-[(2R,3E)-4-[(2S,4'aR,5S,6'R,8'S,8'aR)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2R,3R,6R)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydro-3'H-spiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid

• ChemBase ID: 1926
• Molecular Formular: C44H68O13
• Molecular Mass: 805.00292
• Monoisotopic Mass: 804.46599224
• SMILES: C[C@@H]1CC[C@@]2(CCCCO2)O[C@H]1[C@@H](C)C[C@H](O)[C@@H]1O[C@@H]2CC[C@]3(CC[C@H](O3)/C=C/[C@@H](C)[C@H]3CC(=C[C@]4(O[C@H](CC[C@@H]4O)CC(C)(O)C(=O)O)O3)C)O[C@@H]2[C@@H](O)C1=C
• Canonical SMILES: CC1=C[C@@]2(O[C@H](C1)[C@@H](/C=C/[C@@H]1CC[C@@]3(O1)CC[C@@H]1[C@H](O3)[C@@H](O)C(=C)[C@@H](O1)[C@H](C[C@@H]([C@@H]1O[C@]3(CCCCO3)CC[C@H]1C)C)O)C)O[C@H](CC[C@@H]2O)CC(C(=O)O)(O)C
• InChI: InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30-,31-,32+,33-,34-,35+,36+,37-,38-,39+,41-,42-,43+,44+/m1/s1
• InChIKey: QNDVLZJODHBUFM-NHKYITFXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-[(2R,5S,6S,8R)-8-[(2R,3E)-4-[(2S,4'aR,5S,6'R,8'S,8'aR)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2R,3R,6R)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydro-3'H-spiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid
• IUPAC Traditional name: (2R)-3-[(2R,5S,6S,8R)-8-[(2R,3E)-4-[(2S,4'aR,5S,6'R,8'S,8'aR)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2R,3R,6R)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid
• Synonyms: 9,10-Deepithio-9,10-Didehydroacanthifolicin

Database IDs

• CAS Number: 78111-17-8
• PubChem SID: 160965381; 46504468
• PubChem CID: 46936318

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.761946
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): 3.3957899
• LogD (pH = 7.4): 1.855299
• Log P: 5.134746
• Molar Refractivity: 210.7806 cm^3
• Polarizability: 83.88593 Å^3
• Polar Surface Area: 182.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.73
• LOG S: -5.26
• Solubility (Water): 4.42e-03 g/l

DETAILS

DrugBank - DB02169

• Drug Groups: experimental
• Description: A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. (Thromb Res 1992;67(4):345-54 & Cancer Res 1993;53(2):239-41)