Picrotin
Basic information
- CAS
21416-53-5- Standard SMILES
CC(C)(O)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@]34C(=O)O[C@H]2[C@]14C- InChIKey
RYEFFICCPKWYML-QCGISDTRSA-N- Molecular formula
- C15H18O7
- Average molar mass
- 310.3 g/mol
- Monoisotopic mass
- 310.10525291
Overview
Picrotin is an organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. It has a role as a plant metabolite. It is a picrotoxane sesquiterpenoid, a diol, a tertiary alcohol, an epoxide, a gamma-lactone and an organic heteropentacyclic compound. It is functionally related to a picrotoxinin.
Names & identifiers
- Preferred name
- Picrotin
- IUPAC
- (1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
- English name
- PICROTIN
- Molecular formula
- C15H18O7
- Molecular weight
- 310.3
Names & synonyms
picrotin21416-53-5U06Z6QD7N2CHEBI:8205DTXSID80274161NSC-129536(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo(6.4.1.19,12.03,5.05,13)tetradecane-6,11-dioneRefChem:174200DTXCID5025605(1S,3S,5R,9S,12R,13S,14R)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo(6.4.1.19,12.03,5.05,13)tetradecane-6,11-dioneMFCD00868514
Show more names
Picrotin CRSPicrotin, 10 mM in DMSO(1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-Hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-(1aR,8aS,9S)-1aβ,2,2a,6,6aα,8b-Hexahydro-2aα-hydroxy-9-(1-hydroxy-1-methylethyl)-8bα-methyl-3α,6α-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione
Properties
Computed structural properties
- XLogP
- -0.8
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 644
Experimental & physicochemical properties
Collision Cross Section
173.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
157.6 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 256 · 256-258°C
- alpha
- -64.7 ° · D -64.7° (c = 2.31 in abs alc)
- Boiling point
- 595.8 · 595.8±50.0 °C(Predicted)
- Density
- 1.59 · 1.59
- storage temp.
- 2 · 2-8°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2)(1:9): 0.1 mg/ml
- pka
- 13.28 · 13.28±0.60(Predicted)
- form
- Solid
- color
- White to off-white
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 Z6QD7N2 · U06Z6QD7N2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- TJ8800000
- Toxicity
- LD50 i.p. in mice: 135 mg/kg (Jarboe)
Chemistry & industry
Applications
DescriptionPicrotin is a natural picrotoxane that antagonizes glycine receptors (GlyRs; IC50s = 57 and 117 μM for α1 and α2 homodimeric GlyRs, respectively). It also inhibits α3 homodimeric GlyRs. Picrotin is inactive in inhibiting γ-aminobutyric acid (GABA) type A and type C receptors. Picrotin occurs in the natural plant-derived poison picrotoxin , equimolar with picrotoxinin.
UsesGABAa receptor antagonist
Additional notes
DefinitionChEBI: Picrotin is an organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. It has a role as a plant metabolite. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone, a diol and a picrotoxane sesquiterpenoid. It is functionally related to a picrotoxinin.
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