Identification

PhytoHub ID
PHUB000392
Name
Narirutin
Synonyms
  • Naringenin 7-O-rutinoside
CAS Number
Not Available
Average Mass
580.539
Monoisotopic Mass
580.17920571
Chemical Formula
C27H32O14
IUPAC Name
5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one
InChI Key
HXTFHSYLYXVTHC-TUURGLJWSA-N
InChI Identifier
InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
SMILES
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC(O)=C4C(=O)CC(OC4=C3)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Structure

Calculated Properties

Solubility (ALOGPS)
3.08e+00 g/l
LogS (ALOGPS)
-2.28
LogP (ALOGPS)
-0.35
Hydrogen Acceptors
14
Hydrogen Donors
8
Rotatable Bond Count
6
Polar Surface Area
225.05999999999997
Refractivity
134.30380000000005
Polarizability
56.55559613093156
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-3.6121823516836606
pKa (strongest acidic)
8.579286961223794
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Taxonomy

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavanones

Spectra

Record IDSourceDescriptionView
PM000320ReSpectN/A Spectrum - 35, [M-H]-View Spectra
PM000506ReSpectN/A Spectrum - 35%, [M+H]+View Spectra
PM007417ReSpectN/A Spectrum - 35V, [M-H]-View Spectra

Food Sources

NameGroup
GrapefruitFruit, Citrus PublicationsShow
Grapefruit juiceBeverages, Non-alcoholic PublicationsShow
Orange juiceBeverages, Non-alcoholic PublicationsShow
Sweet orangeFruit, Citrus PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsFormulaMonoisotopic mass
Narirutin Naringenin 4'-O-glucuronidehuman ratplasma (major), urine (major)C21H20O11448.100561464 Publications
Narirutin Naringenin 7-O-glucuronidehuman ratplasma (major), urine (major)C21H20O11448.100561482 Publications
Narirutin Naringenin O-diglucuronidehumanurine (minor)C27H28O17624.5095093 Publications
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