Ajugol
Basic information
- CAS
52949-83-4- Standard SMILES
C[C@]1(O)C[C@@H](O)[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]21- InChIKey
VELYAQRXBJLJAK-XKKWFBPMSA-N- Molecular formula
- C15H24O9
- Average molar mass
- 348.34 g/mol
- Monoisotopic mass
- 348.14203234
Overview
Ajugol is a glycoside and an iridoid monoterpenoid.
Names & identifiers
- Preferred name
- Ajugol
- IUPAC
- (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
- English name
- Ajugol
- Molecular formula
- C15H24O9
- Molecular weight
- 348.35
Names & synonyms
Ajugol52949-83-43W9VFT5UKU.BETA.-D-GLUCOPYRANOSIDE, (1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL(1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL .BETA.-D-GLUCOPYRANOSIDE(1S,4aR,5R,7S,7aS)-1,4a,5,6,7,7a-Hexahydro-5,7-dihydroxy-7-methylcyclopenta[c]pyran-1-yl beta-D-glucopyranoside(2S,3S,4R,5R,6S)-6-(((1R,4AS,7S,7AR)-7-HYDROXY-7-METHYL-1,4A,5,6,7,7A-HEXAHYDROCYCLOPENTA(C)PYRAN-1-YL)OXY)-2-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAOL.BETA.-D-GLUCOPYRANOSIDE, 1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL, (1S-(1.ALPHA.,4A.ALPHA.,5.ALPHA.,7.ALPHA.,7A.ALPHA.))-(1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YL BETA-D-GLUCOPYRANOSIDERefChem:110357BETA-D-GLUCOPYRANOSIDE, (1S,4AR,5R,7S,7AS)-1,4A,5,6,7,7A-HEXAHYDRO-5,7-DIHYDROXY-7-METHYLCYCLOPENTA(C)PYRAN-1-YLbeta-D-Glucopyranoside, 1,4a,5,6,7,7a-hexahydro-5,7-dihydroxy-7-methylcyclopenta(c)pyran-1-yl, (1S-(1alpha,4aalpha,5alpha,7alpha,7aalpha))-
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 149 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 486
Physicochemical properties
- Boiling point
- 617.9 · 617.9±55.0 °C(Predicted)
- Density
- 1.57 · 1.57
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 3.7 mg/mL · DMSO : ≥ 3.7 mg/mL (10.62 mM)
- pka
- 12.8 · 12.80±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- InChI
- InChI=1/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8+,9+,10+,11-,12+,13-,14-,15-/s3
- InChIKey
- VELYAQRXBJLJAK-HWRKDDHMNA-N
- SMILES
- O([C@]1([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H]1OC=C[C@@]2([H])[C@H](O)C[C@@](O)(C)[C@@]12[H] |&1:1,4,7,9,11,13,17,19,22,25,r|
- FDA UNII
- 3 W9VFT5UKU · 3W9VFT5UKU
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
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)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Applications
UsesAjugol is an iridoid glycoside that can be isolated from Leonurus artemisia. Ajugol has anti-protozoal activity againt Trypanosoma b. rhodesiense with an IC50 of 31.8 μg/mL[1].
Suppliers
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Compound notes
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