(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

• ChemBase ID: 126452
• Molecular Formular: C15H22O10
• Molecular Mass: 362.32918
• Monoisotopic Mass: 362.1212969
• SMILES: O1C=C[C@H]2[C@H](O)[C@@H]3O[C@]3(CO)[C@H]2[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/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-/m1/s1
• InChIKey: LHDWRKICQLTVDL-PZYDOOQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-2-{[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0^2,^4]dec-7-en-10-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: catalpol
• Synonyms: Catalpol; (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside; Catalpinoside; Catalpol

Database IDs

• CAS Number: 2415-24-9
• EC Number: 219-324-0
• MDL Number: MFCD11111524
• PubChem SID: 162220786
• PubChem CID: 91520
• CHEMBL: 513223
• Chemspider ID: 82641
• Wikipedia Title: Catalpol

CALCULATED PROPERTIES

• Acid pKa: 12.191621
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.4318037
• LogD (pH = 7.4): -3.4318106
• Log P: -3.4318037
• Molar Refractivity: 77.1915 cm^3
• Polarizability: 32.088512 Å^3
• Polar Surface Area: 161.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• RTECS: LZ5776816
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (HPLC)
• Empirical Formula (Hill Notation): C15H22O10

DETAILS

Sigma Aldrich - 50839

Biochem/physiol Actions
The primary function is to stimulate the production of adrenal cortical hormones, which increases the production of sex hormones. Catalpol also exhibits anti-inflammatory activity and has shown to increase the production of androgens yielded by the adrenal gland, which can lead to increases in muscle mass.