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124-87-8 molecular structure
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(1R,3R,5S,8S,9S,12R,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione; (1R,3R,5S,8S,9S,12R,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

ChemBase ID: 131029
Molecular Formular: C30H34O13
Molecular Mass: 602.58316
Monoisotopic Mass: 602.19994115
SMILES and InChIs

SMILES:
CC(=C)[C@@H]1[C@H]2[C@@H]3[C@@]4([C@]([C@@H]1C(=O)O2)(C[C@@H]1[C@]4(O1)C(=O)O3)O)C.C[C@@]12[C@H]3[C@@H]4[C@H]([C@H]([C@@]1(C[C@@H]1[C@]2(O1)C(=O)O3)O)C(=O)O4)C(C)(C)O
Canonical SMILES:
CC(=C)[C@@H]1[C@@H]2OC(=O)[C@H]1[C@]1([C@]3([C@@H]2OC(=O)[C@]23[C@@H](C1)O2)C)O.O=C1O[C@H]2[C@H]([C@@H]1[C@]1(O)C[C@@H]3[C@]4([C@@]1([C@@H]2OC4=O)C)O3)C(O)(C)C
InChI:
InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7+,8+,9-,13-,14-,15+;6-,7+,8+,9+,10-,13-,14-,15+/m11/s1
InChIKey:
VJKUPQSHOVKBCO-NGKRNLQBSA-N

Cite this record

CBID:131029 http://www.chembase.cn/molecule-131029.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,3R,5S,8S,9S,12R,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione; (1R,3R,5S,8S,9S,12R,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
IUPAC Traditional name
(1R,3R,5S,8S,9S,12R,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione; (1R,3R,5S,8S,9S,12R,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
Synonyms
Cocculin
Picrotoxin
CAS Number
124-87-8
EC Number
204-716-6
MDL Number
MFCD00074824
Beilstein Number
3894406
PubChem SID
24887544
162225307
24278188
PubChem CID
5311359

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5311359 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.596322  H Acceptors
H Donor LogD (pH = 5.5) -1.0787522 
LogD (pH = 7.4) -1.0787524  Log P -1.0787522 
Molar Refractivity 68.2899 cm3 Polarizability 28.414474 Å3
Polar Surface Area 105.59 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
ethanol: soluble50 mg/mL, clear to slightly hazy expand Show data source
Apperance
white to light yellow powder expand Show data source
Melting Point
203 °C(lit.) expand Show data source
RTECS
TJ9100000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
3462 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
28 expand Show data source
Safety Statements
28-36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300 expand Show data source
GHS Precautionary statements
P264-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3462 6.1/PG 2 expand Show data source
Gene Information
human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562) expand Show data source
Purity
98.0% (TLC) expand Show data source
Empirical Formula (Hill Notation)
C30H34O13 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - P1675 external link
Biochem/physiol Actions
GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel.
Other Notes
Molecular complex (1:1) of picrotin and picrotoxinin.
Sigma Aldrich - 80410 external link
Biochem/physiol Actions
GABAA receptor antagonist; binds to the GABA receptor-linked Cl- channel.
Other Notes
GABA receptor antagonist1

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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