(2R)-3-[(1S,2S,2'S,4S,5'R,6R)-4-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-5'-hydroxy-6-methylspiro[3-oxa-7-thiabicyclo[4.1.0]heptane-2,6'-oxane]-2'-yl]-2-hydroxy-2-methylpropanoic acid
Basic information
- CAS
77739-71-0- Standard SMILES
C=C1[C@@H](O)[C@@H]2O[C@]3(CC[C@H](/C=C/[C@@H](C)[C@@H]4C[C@@]5(C)S[C@H]5[C@@]5(O[C@H](C[C@@](C)(O)C(=O)O)CC[C@H]5O)O4)O3)CC[C@H]2O[C@@H]1[C@@H](O)C[C@H](C)[C@H]1O[C@@]2(CCCCO2)CC[C@H]1C- InChIKey
PBZVIYIWLYRXNM-WNFYGIPLSA-N- Molecular formula
- C44H68O13S
- Average molar mass
- 837.1 g/mol
- Monoisotopic mass
- 836.43806339
Overview
PBZVIYIWLYRXNM-WNFYGIPLSA-N has been reported in Pandaros acanthifolium with data available.
Names & identifiers
- Preferred name
- (2R)-3-[(1S,2S,2'S,4S,5'R,6R)-4-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-5'-hydroxy-6-methylspiro[3-oxa-7-thiabicyclo[4.1.0]heptane-2,6'-oxane]-2'-yl]-2-hydroxy-2-methylpropanoic acid
- IUPAC
- (2R)-3-[(1S,2S,2'S,4S,5'R,6R)-4-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-5'-hydroxy-6-methylspiro[3-oxa-7-thiabicyclo[4.1.0]heptane-2,6'-oxane]-2'-yl]-2-hydroxy-2-methylpropanoic acid
- English name
- acanthifolicin
- Molecular formula
- C44H68O13S
- Molecular weight
- 837.07
Names & synonyms
orb1701268DTXSID801383229AKOS040747754T26544acanthifolicinAcanthifolic acidSpiro[3-oxa-7-thiabicyclo[4.1.0]heptane-2,2′-[2H]pyran]-6′-propanoic acid, tetrahydro-α,3′-dihydroxy-α,6-dimethyl-4-[(1R,2E)-1-methyl-3-[(2R,4′aR,5R,6′S,8′R,8′aS)-octahydro-8′-hydroxy-6′-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7′-methylenespiro[furan-2(3H),2′(3′H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-, (αR,1S,2S,3′R,4S,6R,6′S)-
Database identifiers
- CAS
77739-71-0- PubChem CID
- 101970447
- DTXSID
DTXSID801383229
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 208 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 10
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 1,560
Physicochemical properties
- Melting point
- 166 · 166-167 °C
- Boiling point
- 947.4 · 947.4±65.0 °C(predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
- pka
- 3.87 · 3.87±0.16(predicted)
Chemistry & industry
Applications
DescriptionAcanthifolicin is an okadaic acid derivative that has been shown top inhibit protein phosphatase 1 with an IC50= 20 nM (similar to that of okadaic acid at 19 nM).
UsesAcanthifolicin, a derivative of Okadaic acid (HY-N6785), is a protein phosphatase inhibitor. Acanthifolicin inhibits protein phosphatase-1 (PP1) and PP2 with IC50 values of 20 nM and 1 nM, respectively[1].
Additional notes
DefinitionChEBI: Acanthifolicin is a ketal.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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