Picroside I
Basic information
- CAS
27409-30-9- Standard SMILES
O=C(/C=C/c1ccccc1)OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O)[C@@H]4O[C@]4(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O- InChIKey
XZGPUOQGERGURE-LUVHZPKESA-N- Molecular formula
- C24H28O11
- Average molar mass
- 492.5 g/mol
- Monoisotopic mass
- 492.16316171
Overview
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-10-yl]oxy}oxan-2-yl]methyl (2E)-3-phenylprop-2-enoate has been reported in Gentiana kurroo and Picrorhiza kurrooa with data available.
Names & identifiers
- Preferred name
- Picroside I
- IUPAC
- [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxan-2-yl]methyl (E)-3-phenylprop-2-enoate
- English name
- PICROSIDE I
- Molecular formula
- C24H28O11
- Molecular weight
- 492.47
Names & synonyms
Picroside I27409-30-9DTXSID101318188[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]oxan-2-yl]methyl (E)-3-phenylprop-2-enoate((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-10-yl)oxy)oxan-2-yl)methyl (E)-3-phenylprop-2-enoateRefChem:174196DTXCID401747976((2R,3S,4S,5R,6S)-6-(((1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno(5,6)cyclopenta(1,3-c)pyran-2-yl)oxy)-3,4,5-trihydroxyoxan-2-yl)methyl (E)-3-phenylprop-2-enoate248-445-16'-CinnamoylcatalpolAmphicoside IMFCD29505480
Show more names
PicrosideⅠPicroside-ⅠAmphicoside ⅠAmphicoside ⅠAmphicoside Ⅰ3Picroside I-RMPicroside I(AS)PICOLINIC ACID(P)
((2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(((1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl cinnamatePicroside-IPicroside 1Picroside I (Standard)DKB2JY964APicroside 1 (Globularicisin)CHEMBL454577orb1305018
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 168 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 8
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 826
Physicochemical properties
- Boiling point
- 778.6 · 778.6±60.0 °C(Predicted)
- Density
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/mL, · ethanol: soluble1mg/mL, clear, colorless
- form
- powder
- pka
- 12.7 · 12.70±0.70(Predicted)
- color
- White
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- BSYHSWKTXMTFNF-NTLZGZQOSA-N
- SMILES
- [C@]12(CO)O[C@H]1[C@H]([C@]1([H])C=CO[C@@H](O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@]21[H])OC(=O)/C=C/C1=CC=CC=C1 |&1:0,4,5,6,11,13,14,16,17,19,24,r|
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Applications
DescriptionPicroliv is a hepatoprotective mixture of compounds that is isolated from an herb native to the Himalayas. Picroside I is an iridoid glycoside found in picroliv. By itself, picroside I blocks changes in acid phosphatase activity, phospholipid levels, and lipid peroxide production induced by D-galactosamine in rat liver. Picroside I also enhances neurite outgrowth in PC12D cells induced by basic fibroblast growth factor and 7S nerve growth factor when given at 60 μM. At concentrations as low as 5 μM, picroside I enhances the ATPase activity of the efflux transporter P-glycoprotein.
UsesPicroside I acts as an oxygen free radical scavenger and thus promotes anti-inflammatory activity and may be used in the treatment of arthritis.
Related reactions
0 records
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Compound notes
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