7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 133763
• Molecular Formular: C27H32O14
• Molecular Mass: 580.53458
• Monoisotopic Mass: 580.1792057
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1cc(c2c(c1)OC(CC2=O)c1ccc(cc1)O)O)CO)O)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]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChIKey: DFPMSGMNTNDNHN-JJLSSNRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
• Synonyms: 4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside; Naringenine-7-rhamnosidoglucoside; Naringin

Database IDs

• CAS Number: 10236-47-2
• EC Number: 233-566-4
• MDL Number: MFCD00148888
• Beilstein Number: 102012
• PubChem SID: 162228040; 24897483; 24886149
• PubChem CID: 25075

CALCULATED PROPERTIES

• Acid pKa: 9.315869
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -0.15695165
• LogD (pH = 7.4): -0.16210435
• Log P: -0.15688573
• Molar Refractivity: 134.3038 cm^3
• Polarizability: 54.11746 Å^3
• Polar Surface Area: 225.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -80±10°, c = 1% in ethanol

Safety Information

• RTECS: QN6340000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-24/25; 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥90%; ≥95% (HPLC)
• Biological Source: from citrus fruit
• Empirical Formula (Hill Notation): C27H32O14

DETAILS

Sigma Aldrich - N1376

Biochem/physiol Actions
Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.1
包装
25, 100 g in poly bottle

Sigma Aldrich - 71162

Biochem/physiol Actions
Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.1