7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

• ChemBase ID: 155929
• Molecular Formular: C26H28O14
• Molecular Mass: 564.49212
• Monoisotopic Mass: 564.14790558
• SMILES: c1cc(ccc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]1[C@H]([C@](CO1)(CO)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@]([C@@H]1O)(O)CO
• InChI: InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23-,24-,25+,26-/m1/s1
• InChIKey: NTDLXWMIWOECHG-MFMSCHSJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3S,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• Synonyms: Apigenin-7-(2-O-apiosylglucoside); Apiin

Database IDs

• CAS Number: 26544-34-3
• EC Number: 247-780-0
• MDL Number: MFCD00016941
• PubChem SID: 162250067; 24850695
• PubChem CID: 16211399

CALCULATED PROPERTIES

• Acid pKa: 8.30543
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.8385525
• LogD (pH = 7.4): -0.88977826
• Log P: -0.83787805
• Molar Refractivity: 131.7285 cm^3
• Polarizability: 52.107494 Å^3
• Polar Surface Area: 225.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C26H28O14

DETAILS

Sigma Aldrich - 17784

Biochem/physiol Actions
Apiin, a major flavonoid component of celery, shows antiinflammatory activity mediated through inhibition of nitric oxide synthesis and inhibition of iNOS expression.1