Catalpol
Basic information
- CAS
2415-24-9- Standard SMILES
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
LHDWRKICQLTVDL-PZYDOOQISA-N- Molecular formula
- C15H22O10
- Average molar mass
- 362.33 g/mol
- Monoisotopic mass
- 362.12129689
Overview
Catalpol is an organic molecular entity. It has a role as a metabolite.
Names & identifiers
- Preferred name
- Catalpol
- IUPAC
- (2S,3R,4S,5S,6R)-2-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
- English name
- Catalpol
- Molecular formula
- C15H22O10
- Molecular weight
- 362.33
Names & synonyms
Catalpol2415-24-9JCX5L7JIC2DTXSID60178850(2S,3R,4S,5S,6R)-2-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol(2S,3R,4S,5S,6R)-2-(((1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo(4.4.0.02,4)dec-7-en-10-yl)oxy)-6-(hydroxymethyl)oxane-3,4,5-triolRefChem:31875DTXCID20101341(2S,3R,4S,5S,6R)-2-(((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)-6-(hydroxymethyl)oxane-3,4,5-triol219-324-0CatalpinosideMFCD11111524
Show more names
CATAPOLCatalpol-RMCatapol ,>=98%Catalpol，CatalnolCatalpol 2415-24-9CATALPOL WITH HPLC,6-beta,6a-alpha))-
CHEMBL513223Catalpol CRSCHEBI:69797De(p-hydroxybenzoyl)catalposide(2S,3R,4S,5S,6R)-2-(((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)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolCatalposide, des-p-hydroxybenzoyl-SR-05000002315-2Catalpol (Standard)
Properties
Computed structural properties
- XLogP
- -3.2
- Topological polar surface area
- 162 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 542
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Physicochemical properties
- Melting point
- 203 · 203-205°C
- Boiling point
- 675.6 · 675.6±55.0 °C(Predicted)
- Density
- 1.72 · 1.72±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
- form
- Solid
- pka
- 12.79 · 12.79±0.70(Predicted)
- color
- White to Off-White
- InChI
- InChI=1/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/s3
- InChIKey
- LHDWRKICQLTVDL-CLLMHHLUSA-N
- SMILES
- C([C@]12O[C@H]1[C@@H](O)[C@]1([H])C=CO[C@@H](O[C@@]3([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@]21[H])O |&1:1,3,4,6,11,13,15,16,18,20,25,r|
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
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCatalpol: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- LZ5776816
- hs_code
- 29389090
- Toxicity
- mouse,LD,intravenous,> 2500mg/kg (2500mg/kg),Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 93, 1968.
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
Chemistry & industry
Applications
DescriptionCatalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties. It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 μM. Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 μg/ml and 25 to 100 mg/kg, respectively. In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.
UsesCatapol is an iridoid glucoside that has been shown to alleviate neuropathic pain.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Catalpol is an organic molecular entity. It has a role as a metabolite.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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