NP-MRD: Showing NP-Card for Hesperidin (NP0000675)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:45 UTC

Updated at

2024-09-03 04:18:44 UTC

NP-MRD ID

NP0000675

Natural Product DOI

https://doi.org/10.57994/1495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hesperidin

Description

Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit. Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit due to vitamin C deficiency such as bruising due to capillary fragility were found in early studies to be relieved by crude vitamin C extract but not by purified vitamin C. The bioflavonoids, formerly called "vitamin P", were found to be the essential components in correcting this bruising tendency and improving the permeability and integrity of the capillary lining. These bioflavonoids include hesperidin, citrin, rutin, flavones, flavonols, catechin and quercetin. Of historical importance is the observation that "citrin", a mixture of two flavonoids, eriodictyol and hesperidin, was considered to possess a vitamin-like activity, as early as in 1949. Hesperidin deficiency has since been linked with abnormal capillary leakiness as well as pain in the extremities causing aches, weakness and night leg cramps. Supplemental hesperidin also helps in reducing oedema or excess swelling in the legs due to fluid accumulation. As with other bioflavonoids, hesperidin works best when administered concomitantly with vitamin C. No signs of toxicity have been observed with normal intake of hesperidin. Hesperidin was first discovered in 1827, by Lebreton, but not in a pure state and has been under continuous investigation since then (PMID: 11746857 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB03236.mol
  Mrv1652305271900152D          

 43 47  0  0  0  0            999 V2000
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  1 34  1  6  0  0  0
  5 43  1  0  0  0  0
M  END

HMDB0003265
     RDKit          3D
Hesperidin
 77 81  0  0  0  0  0  0  0  0999 V2000
    9.4341    3.5854    3.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1725    3.7751    2.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5548    2.6925    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1547    1.4436    2.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5153    0.3689    1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2896    0.5630    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170   -0.6008    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7312   -0.5335   -1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088   -1.7007   -1.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -2.5281   -2.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.8275   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB03236.mol
  Mrv1652305271900152D          

 43 47  0  0  0  0            999 V2000
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   -4.6441    0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3585   -0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0730    0.2062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0730    1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3585    1.4437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3585    2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7875    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7875   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3585   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  3 11  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 25 28  1  6  0  0  0
 24 29  1  6  0  0  0
 23 30  1  6  0  0  0
 22 20  1  6  0  0  0
 19 20  1  0  0  0  0
 18 19  1  1  0  0  0
 17 31  1  1  0  0  0
 16 32  1  1  0  0  0
 15 33  1  6  0  0  0
 12 14  1  0  0  0  0
  7 12  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 34 39  2  0  0  0  0
 40 41  1  0  0  0  0
 37 40  1  0  0  0  0
 36 42  1  0  0  0  0
  1 34  1  6  0  0  0
  5 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000675

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(OC1O[C@H](CO[C@H]3O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H](O)[C@H]1O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21+,22-,23+,24-,25+,26+,27-,28?/m0/s1

> <INCHI_KEY>
QUQPHWDTPGMPEX-UNZJSITISA-N

> <FORMULA>
C28H34O15

> <MOLECULAR_WEIGHT>
610.5606

> <EXACT_MASS>
610.189770418

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
59.87068866808306

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.31455698766666607

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.819837030926854

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.609445995469539

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
140.767

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hesperidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003265
     RDKit          3D
Hesperidin
 77 81  0  0  0  0  0  0  0  0999 V2000
    9.4341    3.5854    3.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1725    3.7751    2.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5548    2.6925    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1547    1.4436    2.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5153    0.3689    1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2896    0.5630    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170   -0.6008    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7312   -0.5335   -1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088   -1.7007   -1.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -2.5281   -2.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.8275   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -2.4315   -1.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9468   -2.9510   -3.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.5373   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -2.0254   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555   -2.0873    0.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491   -2.6145   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -1.6934   -0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281   -1.9701   -1.5254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6081   -1.3154   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    0.0542   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    0.7857   -1.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4435    1.4676    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3818    2.4257    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0015    3.0999    1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    3.4650   -0.6996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1594    4.7259   -0.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5434    3.1682   -1.8167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2388    3.2664   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279    1.7268   -2.2324 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7764    1.4648   -3.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -3.4755   -1.6290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7610   -3.7363   -2.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -4.1399   -0.2833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2312   -3.6862    0.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897   -3.8652    0.2647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0910   -4.9671    0.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0157   -1.4101    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.2961    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815   -0.6925    0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7259    1.8071    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    2.9004    1.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7597    4.1624    1.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8333    4.5259    3.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3177    2.7890    4.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1080    3.1466    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292    1.2898    2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0072   -0.5791    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1177   -1.5377    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8016   -0.5347   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    0.4134   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081   -2.9467   -3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063   -3.0159   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -2.8975   -1.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869   -1.5475   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.8023   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1665   -1.5069   -2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    0.0846   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4121    2.0180    0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    2.4412    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4505    4.0370    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579    3.3038    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5346    3.5679   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507    5.2399    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    3.8293   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2553    3.9548   -0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7172    1.6151   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9121    1.8178   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -3.8660   -2.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072   -4.2578   -2.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787   -5.2313   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -4.0759    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -3.6382    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7465   -5.3589    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -1.0156    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    1.9530    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2510    4.9219    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 15 38  1  0
 38 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  2  0
 42 43  1  0
 42  3  1  0
 40  7  1  0
 39 11  1  0
 36 17  1  0
 30 22  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  4 47  1  0
  5 48  1  0
  7 49  1  1
  8 50  1  0
  8 51  1  0
 13 52  1  0
 14 53  1  0
 17 54  1  0
 19 55  1  6
 20 56  1  0
 20 57  1  0
 22 58  1  1
 24 59  1  1
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  6
 27 64  1  0
 28 65  1  6
 29 66  1  0
 30 67  1  6
 31 68  1  0
 32 69  1  6
 33 70  1  0
 34 71  1  6
 35 72  1  0
 36 73  1  1
 37 74  1  0
 38 75  1  0
 41 76  1  0
 43 77  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03236.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       6.002  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.002  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.668  -2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.668  -4.235   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.667   0.385   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.334   0.385   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001  -1.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.334  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.668  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.668  -0.385   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.002   0.385   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.335  -0.385   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -8.669   1.925   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.669   0.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.003  -0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.336   0.385   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.336   1.925   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.003   2.695   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.003   4.235   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -12.670   2.695   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -12.670  -0.385   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -10.003  -1.925   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.002  -2.695   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.334  -4.235   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.667  -2.695   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.335   0.385   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.335   1.925   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.669   2.695   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.003   1.925   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.003   0.385   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.669  -0.385   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      11.336   2.695   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      12.670   1.925   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.669   4.235   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.001  -4.235   0.000  0.00  0.00           O+0
CONECT    1    2   10   34                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   43                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    1                                                       
CONECT   11    3                                                            
CONECT   12   14    7                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15   12                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   13   19                                                  
CONECT   19   20   18                                                       
CONECT   20   22   19                                                       
CONECT   21   22   26                                                       
CONECT   22   21   23   20                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   17                                                            
CONECT   32   16                                                            
CONECT   33   15                                                            
CONECT   34   35   39    1                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   41   37                                                       
CONECT   41   40                                                            
CONECT   42   36                                                            
CONECT   43    5                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

COMPND    HMDB0003265
HETATM    1  C1  UNL     1       9.434   3.585   3.542  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.172   3.775   2.940  1.00  0.00           O  
HETATM    3  C2  UNL     1       7.555   2.693   2.343  1.00  0.00           C  
HETATM    4  C3  UNL     1       8.155   1.444   2.331  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.515   0.369   1.726  1.00  0.00           C  
HETATM    6  C5  UNL     1       6.290   0.563   1.144  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.617  -0.601   0.491  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.731  -0.533  -1.000  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.009  -1.701  -1.583  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.494  -2.528  -2.367  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.602  -1.828  -1.152  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.670  -2.432  -1.955  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.947  -2.951  -3.186  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.338  -2.537  -1.513  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.026  -2.025  -0.285  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.256  -2.087   0.220  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.349  -2.614  -0.451  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.425  -1.693  -0.444  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.228  -1.970  -1.525  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.608  -1.315  -1.358  1.00  0.00           C  
HETATM   21  O6  UNL     1      -4.426   0.054  -1.240  1.00  0.00           O  
HETATM   22  C16 UNL     1      -5.573   0.786  -1.060  1.00  0.00           C  
HETATM   23  O7  UNL     1      -5.444   1.468   0.143  1.00  0.00           O  
HETATM   24  C17 UNL     1      -6.382   2.426   0.382  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.002   3.100   1.699  1.00  0.00           C  
HETATM   26  C19 UNL     1      -6.495   3.465  -0.700  1.00  0.00           C  
HETATM   27  O8  UNL     1      -6.159   4.726  -0.174  1.00  0.00           O  
HETATM   28  C20 UNL     1      -5.543   3.168  -1.817  1.00  0.00           C  
HETATM   29  O9  UNL     1      -4.239   3.266  -1.314  1.00  0.00           O  
HETATM   30  C21 UNL     1      -5.728   1.727  -2.232  1.00  0.00           C  
HETATM   31  O10 UNL     1      -4.776   1.465  -3.238  1.00  0.00           O  
HETATM   32  C22 UNL     1      -3.433  -3.476  -1.629  1.00  0.00           C  
HETATM   33  O11 UNL     1      -4.761  -3.736  -2.031  1.00  0.00           O  
HETATM   34  C23 UNL     1      -3.254  -4.140  -0.283  1.00  0.00           C  
HETATM   35  O12 UNL     1      -4.231  -3.686   0.600  1.00  0.00           O  
HETATM   36  C24 UNL     1      -1.890  -3.865   0.265  1.00  0.00           C  
HETATM   37  O13 UNL     1      -1.091  -4.967   0.080  1.00  0.00           O  
HETATM   38  C25 UNL     1       2.016  -1.410   0.511  1.00  0.00           C  
HETATM   39  C26 UNL     1       3.323  -1.296   0.100  1.00  0.00           C  
HETATM   40  O14 UNL     1       4.282  -0.692   0.886  1.00  0.00           O  
HETATM   41  C27 UNL     1       5.726   1.807   1.174  1.00  0.00           C  
HETATM   42  C28 UNL     1       6.322   2.900   1.761  1.00  0.00           C  
HETATM   43  O15 UNL     1       5.760   4.162   1.795  1.00  0.00           O  
HETATM   44  H1  UNL     1       9.833   4.526   3.979  1.00  0.00           H  
HETATM   45  H2  UNL     1       9.318   2.789   4.321  1.00  0.00           H  
HETATM   46  H3  UNL     1      10.108   3.147   2.769  1.00  0.00           H  
HETATM   47  H4  UNL     1       9.129   1.290   2.793  1.00  0.00           H  
HETATM   48  H5  UNL     1       8.007  -0.579   1.736  1.00  0.00           H  
HETATM   49  H6  UNL     1       6.118  -1.538   0.812  1.00  0.00           H  
HETATM   50  H7  UNL     1       6.802  -0.535  -1.307  1.00  0.00           H  
HETATM   51  H8  UNL     1       5.287   0.413  -1.346  1.00  0.00           H  
HETATM   52  H9  UNL     1       3.808  -2.947  -3.645  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.606  -3.016  -2.146  1.00  0.00           H  
HETATM   54  H11 UNL     1      -1.194  -2.898  -1.500  1.00  0.00           H  
HETATM   55  H12 UNL     1      -2.787  -1.547  -2.427  1.00  0.00           H  
HETATM   56  H13 UNL     1      -5.084  -1.802  -0.513  1.00  0.00           H  
HETATM   57  H14 UNL     1      -5.167  -1.507  -2.286  1.00  0.00           H  
HETATM   58  H15 UNL     1      -6.431   0.085  -1.056  1.00  0.00           H  
HETATM   59  H16 UNL     1      -7.412   2.018   0.556  1.00  0.00           H  
HETATM   60  H17 UNL     1      -5.310   2.441   2.300  1.00  0.00           H  
HETATM   61  H18 UNL     1      -5.450   4.037   1.524  1.00  0.00           H  
HETATM   62  H19 UNL     1      -6.858   3.304   2.343  1.00  0.00           H  
HETATM   63  H20 UNL     1      -7.535   3.568  -1.072  1.00  0.00           H  
HETATM   64  H21 UNL     1      -6.951   5.240   0.107  1.00  0.00           H  
HETATM   65  H22 UNL     1      -5.702   3.829  -2.668  1.00  0.00           H  
HETATM   66  H23 UNL     1      -4.255   3.955  -0.624  1.00  0.00           H  
HETATM   67  H24 UNL     1      -6.717   1.615  -2.726  1.00  0.00           H  
HETATM   68  H25 UNL     1      -3.912   1.818  -2.934  1.00  0.00           H  
HETATM   69  H26 UNL     1      -2.749  -3.866  -2.380  1.00  0.00           H  
HETATM   70  H27 UNL     1      -4.807  -4.258  -2.852  1.00  0.00           H  
HETATM   71  H28 UNL     1      -3.379  -5.231  -0.439  1.00  0.00           H  
HETATM   72  H29 UNL     1      -4.106  -4.076   1.494  1.00  0.00           H  
HETATM   73  H30 UNL     1      -1.887  -3.638   1.365  1.00  0.00           H  
HETATM   74  H31 UNL     1      -0.746  -5.359   0.917  1.00  0.00           H  
HETATM   75  H32 UNL     1       1.735  -1.016   1.479  1.00  0.00           H  
HETATM   76  H33 UNL     1       4.750   1.953   0.707  1.00  0.00           H  
HETATM   77  H34 UNL     1       6.251   4.922   2.242  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3
CONECT    3    4    4   42
CONECT    4    5   47
CONECT    5    6    6   48
CONECT    6    7   41
CONECT    7    8   40   49
CONECT    8    9   50   51
CONECT    9   10   10   11
CONECT   11   12   12   39
CONECT   12   13   14
CONECT   13   52
CONECT   14   15   15   53
CONECT   15   16   38
CONECT   16   17
CONECT   17   18   36   54
CONECT   18   19
CONECT   19   20   32   55
CONECT   20   21   56   57
CONECT   21   22
CONECT   22   23   30   58
CONECT   23   24
CONECT   24   25   26   59
CONECT   25   60   61   62
CONECT   26   27   28   63
CONECT   27   64
CONECT   28   29   30   65
CONECT   29   66
CONECT   30   31   67
CONECT   31   68
CONECT   32   33   34   69
CONECT   33   70
CONECT   34   35   36   71
CONECT   35   72
CONECT   36   37   73
CONECT   37   74
CONECT   38   39   39   75
CONECT   39   40
CONECT   41   42   42   76
CONECT   42   43
CONECT   43   77
END

HMDB0003265
     RDKit          3D
Hesperidin
 77 81  0  0  0  0  0  0  0  0999 V2000
    9.4341    3.5854    3.5424 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1725    3.7751    2.9401 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5548    2.6925    2.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1547    1.4436    2.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5153    0.3689    1.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2896    0.5630    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6170   -0.6008    0.4911 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7312   -0.5335   -1.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088   -1.7007   -1.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4936   -2.5281   -2.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -1.8275   -1.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -2.4315   -1.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9468   -2.9510   -3.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3381   -2.5373   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0257   -2.0254   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2555   -2.0873    0.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3491   -2.6145   -0.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -1.6934   -0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281   -1.9701   -1.5254 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6081   -1.3154   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    0.0542   -1.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    0.7857   -1.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4435    1.4676    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3818    2.4257    0.3819 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0015    3.0999    1.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4954    3.4650   -0.6996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1594    4.7259   -0.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5434    3.1682   -1.8167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2388    3.2664   -1.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279    1.7268   -2.2324 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7764    1.4648   -3.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -3.4755   -1.6290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7610   -3.7363   -2.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   -4.1399   -0.2833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2312   -3.6862    0.5996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897   -3.8652    0.2647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0910   -4.9671    0.0800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0157   -1.4101    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225   -1.2961    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815   -0.6925    0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7259    1.8071    1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    2.9004    1.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7597    4.1624    1.7947 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8333    4.5259    3.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3177    2.7890    4.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1080    3.1466    2.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292    1.2898    2.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0072   -0.5791    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1177   -1.5377    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8016   -0.5347   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2868    0.4134   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8081   -2.9467   -3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063   -3.0159   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -2.8975   -1.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869   -1.5475   -2.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842   -1.8023   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1665   -1.5069   -2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4311    0.0846   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4121    2.0180    0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3104    2.4412    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4505    4.0370    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8579    3.3038    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5346    3.5679   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9507    5.2399    0.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7020    3.8293   -2.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2553    3.9548   -0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7172    1.6151   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9121    1.8178   -2.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -3.8660   -2.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072   -4.2578   -2.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3787   -5.2313   -0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1060   -4.0759    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -3.6382    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7465   -5.3589    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348   -1.0156    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499    1.9530    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2510    4.9219    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 19 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 15 38  1  0
 38 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  2  0
 42 43  1  0
 42  3  1  0
 40  7  1  0
 39 11  1  0
 36 17  1  0
 30 22  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  4 47  1  0
  5 48  1  0
  7 49  1  1
  8 50  1  0
  8 51  1  0
 13 52  1  0
 14 53  1  0
 17 54  1  0
 19 55  1  6
 20 56  1  0
 20 57  1  0
 22 58  1  1
 24 59  1  1
 25 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  6
 27 64  1  0
 28 65  1  6
 29 66  1  0
 30 67  1  6
 31 68  1  0
 32 69  1  6
 33 70  1  0
 34 71  1  6
 35 72  1  0
 36 73  1  1
 37 74  1  0
 38 75  1  0
 41 76  1  0
 43 77  1  0
M  END

View in JSmol

Synonyms

Value	Source
7-Rhamnoglucoside, hesperetin	HMDB
Hesperetin 7-rhamnoglucoside	HMDB
Hesperetin-7-rutinoside	HMDB
Atripliside b	HMDB
Hesperetin 7 rhamnoglucoside	HMDB
Hesperetin 7 rutinoside	HMDB
(2S)-Hesperidin	HMDB
(S)-(-)-Hesperidin	HMDB
Cirantin	HMDB
Ciratin	HMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-a-L-rhamnosyl-D-glucoside) (7ci)	HMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-alpha-L-rhamnosyl-delta-glucoside) (7ci)	HMDB
Hesper bitabs	HMDB
Hesperetin 7-O-rutinoside	HMDB
Hesperetin-rutinoside	HMDB
Hesperidine	HMDB
Hesperidoside	HMDB
Hesperitin-7-rhamnoglucoside	HMDB
Hesperidin	MeSH

Chemical Formula

C₂₈H₃₄O₁₅

Average Mass

610.5606 Da

Monoisotopic Mass

610.18977 Da

IUPAC Name

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

Traditional Name

hesperidine

CAS Registry Number

520-26-3

SMILES

COC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(OC1O[C@H](CO[C@H]3O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H](O)[C@H]1O)C=C2O

InChI Identifier

InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21+,22-,23+,24-,25+,26+,27-,28?/m0/s1

InChI Key

QUQPHWDTPGMPEX-UNZJSITISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Agathosma betulina	LOTUS Database	35616633
Allium fistulosum	FooDB	PHENOL EXPLORER
Artemisia capillaris	LOTUS Database	35616633
Aster souliei	LOTUS Database	35616633
Baccharis magellanica	KNApSAcK Database	22123792
Betula pendula	LOTUS Database	35616633
Calicotome villosa	LOTUS Database	35616633
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	Plant	KNApSAcK
Chrysanthemum morifolium	LOTUS Database	35616633
Citrus aurantiifolia	FooDB	PHENOL EXPLORER
Citrus aurantium	LOTUS Database	35616633
Citrus aurantium L. var. amara	KNApSAcK Database	22123792
Citrus hystrix	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	FooDB	PHENOL EXPLORER
Citrus medica	LOTUS Database	35616633
Citrus natsudaidai	KNApSAcK Database	22123792
Citrus paradisi	FooDB	PHENOL EXPLORER
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus sinensis	LOTUS Database	35616633
Citrus spp.	KNApSAcK Database	22123792
Citrus sudachi	KNApSAcK Database	22123792
Citrus trifoliata	Plant	KNApSAcK
Citrus unshiu	LOTUS Database	35616633
Citrus unshiu Markovich	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cyclopia falcata	LOTUS Database	35616633
Drummondita calida	LOTUS Database	35616633
Ephedra sinica	KNApSAcK Database	22123792
Esenbeckia yaxhoob Lundell	KNApSAcK Database	22123792
Euodia hupehensis	LOTUS Database	35616633
Ficus beecheyana	KNApSAcK Database	22123792
Ficus erecta	LOTUS Database	35616633
Flindersia acuminata	LOTUS Database	35616633
Flindersia collina	LOTUS Database	35616633
Flindersia laevicarpa	LOTUS Database	35616633
Flindersia laevicarpa C.T.White et Francis.	KNApSAcK Database	22123792
Flindersia xanthoxyla	LOTUS Database	35616633
Glandularia bipinnatifida	Plant	KNApSAcK
Humulus lupulus	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hyssopus spp.	KNApSAcK Database	22123792
Mentha	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha arvensis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha longifolia	KNApSAcK Database	22123792
Mentha piperita	LOTUS Database	35616633
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha spp.	KNApSAcK Database	22123792
Mentha x piperita	FooDB	PHENOL EXPLORER
Myrtus communis	LOTUS Database	35616633
Polygonatum odoratum	LOTUS Database	35616633
Poncirus trifoliata	KNApSAcK Database	22123792
Portulaca oleracea	LOTUS Database	35616633
Rosmarinus officinalis	KNApSAcK Database	22123792
Rutaceae	-	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Schizonepeta tenuifolia	LOTUS Database	35616633
Taxus chinensis	KNApSAcK Database	22123792
Thymus vulgaris	LOTUS Database	35616633
Tilia L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Turnera ulmifolia	Plant	KNApSAcK
Valeriana officinalis	LOTUS Database	35616633
Verbascum phlomoides	LOTUS Database	35616633
Verbena hybrida	Plant	KNApSAcK
Vernonanthura divaricata	LOTUS Database	35616633
Vernonia spp.	KNApSAcK Database	22123792
Viola arvensis	LOTUS Database	35616633
Zanthoxylum avicennae	LOTUS Database	35616633
Zanthoxylum dipetalum	KNApSAcK Database	22123792
Zanthoxylum gilletii	LOTUS Database	35616633
Zanthoxylum leprieurii	LOTUS Database	35616633
Zanthoxylum nitidum	LOTUS Database	35616633
Zanthoxylum rhoifolium	LOTUS Database	35616633
Zanthoxylum scandens	LOTUS Database	35616633
Zanthoxylum zanthoxyloides	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	262 °C	Not Available
Boiling Point	930.00 to 931.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2125 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-1.212 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	2.69 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.77 m³·mol⁻¹	ChemAxon
Polarizability	59.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0003265

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hesperidin

METLIN ID

3678

PubChem Compound

53477767

PDB ID

Not Available

ChEBI ID

28775

Good Scents ID

rw1108831

References

General References

Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81. [PubMed:15351063 ]
Nielsen IL, Chee WS, Poulsen L, Offord-Cavin E, Rasmussen SE, Frederiksen H, Enslen M, Barron D, Horcajada MN, Williamson G: Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: a randomized, double-blind, crossover trial. J Nutr. 2006 Feb;136(2):404-8. [PubMed:16424119 ]
Li QS, Lou GY, Qian MZ: [Effect of hesperidin and rutin on oxidative modification of high density lipoprotein in vitro]. Zhong Xi Yi Jie He Xue Bao. 2004 Mar;2(2):115-6, 119. [PubMed:15339471 ]
Lee NK, Choi SH, Park SH, Park EK, Kim DH: Antiallergic activity of hesperidin is activated by intestinal microflora. Pharmacology. 2004 Aug;71(4):174-80. [PubMed:15240993 ]
Garg A, Garg S, Zaneveld LJ, Singla AK: Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Phytother Res. 2001 Dec;15(8):655-69. [PubMed:11746857 ]

Showing NP-Card for Hesperidin (NP0000675)

MOL for NP0000675 (Hesperidin)

3D MOL for NP0000675 (Hesperidin)

3D SDF for NP0000675 (Hesperidin)

3D-SDF for NP0000675 (Hesperidin)

PDB for NP0000675 (Hesperidin)

3D PDB for NP0000675 (Hesperidin)

SMILES for NP0000675 (Hesperidin)

INCHI for NP0000675 (Hesperidin)

Structure for NP0000675 (Hesperidin)

3D Structure for NP0000675 (Hesperidin)