NP-MRD: Showing NP-Card for Rhoifolin (NP0043960)

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Record Information

Version

1.0

Created at

2021-06-22 17:42:54 UTC

Updated at

2021-08-20 00:00:49 UTC

NP-MRD ID

NP0043960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhoifolin

Description

Apigenin 7-O-beta-D-rutinoside, also known as rhoifolin or apigenin-7-O-rhamnoglucoside, 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. Apigenin 7-O-beta-D-rutinoside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Rhoifolin is found in Acmella oleracea, Acorus calamus, Astragalus peregrinus, Asystasia gangetica, Bryum pseudotriquetrum, Carallia brachiata, Chrysanthemum morifolium, Citrus maxima, Citrus sinensis, Citrus unshiu, Euchresta japonica, Gnetum africanum, Gonocaryum calleryanum, Kummerowia striata, Lawsonia alba , Lawsonia inermis, Lonicera gracilipes, Lonicera japonica, Lupinus luteus, Plagiomnium ciliare, Pyrrosia serpens, Reichardia picroides, Toxicodendron sylvestre, Serenoa repens, Syringa persica, Toxicodendron succedaneum, Trachelospermum jasminoides and Valeriana hardwickii . It was first documented in 2004 (PMID: 15631081). Based on a literature review a significant number of articles have been published on Apigenin 7-O-beta-D-rutinoside (PMID: 27719955) (PMID: 15974126) (PMID: 19771866) (PMID: 20222420).

Structure

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


  Mrv1652306222119422D          

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  4 40  1  1  0  0  0
  3 41  1  6  0  0  0
M  END

NP0043960
     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306222119422D          

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    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  6  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 18 34  1  0  0  0  0
 12 35  1  1  0  0  0
 35 36  1  0  0  0  0
 11 37  1  6  0  0  0
 10 38  1  1  0  0  0
  5 39  1  1  0  0  0
  4 40  1  1  0  0  0
  3 41  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0043960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/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/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
RPMNUQRUHXIGHK-PYXJVEIZSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.5187

> <EXACT_MASS>
578.163555668

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
56.77391073360466

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
-0.28530463866666605

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.741302488439352

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2976229448889365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925693394505

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
135.92789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rhoifolin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043960
     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
   -2.1333   -0.7411    2.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -2.1314    2.3711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9954   -2.3352    1.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047   -2.6332    0.1911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6784   -2.3227   -1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -1.3409   -1.6613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5830   -0.1710   -2.0661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7735    0.3195   -1.0456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6654   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.6161   -2.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    0.9781   -2.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664    0.9006   -3.6987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    1.3900   -1.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773    1.7522   -1.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2434    1.7299   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090    2.1574   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.1903    1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210    2.6081    2.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    2.6438    3.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9368    3.0258    4.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    3.3778    4.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920    3.7703    5.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0319    3.3499    3.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4395    2.9619    2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2409    1.8328    0.9739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.4437   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2748    1.0829   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966    0.8947   -2.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    0.5451   -3.7480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7549    1.7436   -4.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318    2.8565   -4.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655   -0.5568   -3.4371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7148   -0.9037   -4.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -1.7565   -2.9212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1421   -2.7541   -2.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4571   -4.0545    0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7805   -4.2329   -0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -4.4348    1.8701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5233   -5.2221    2.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788   -3.2132    2.7736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1423   -3.6923    4.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482   -0.7965    2.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.1874    3.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.1839    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -2.1342    3.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8781   -1.9714    0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345   -0.9608   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591   -0.4822   -2.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7682    0.3109   -3.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491    1.0940   -3.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2504    2.4448   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    2.3619    3.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    3.0601    5.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3281    3.0653    6.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917    3.6231    3.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0853    2.9534    1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    1.1395    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238    0.2110   -4.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988    1.5512   -5.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6028    1.9973   -3.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057    2.8982   -3.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133   -0.1839   -2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2831   -0.1184   -4.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -2.1148   -3.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9532   -2.3091   -2.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564   -4.7964   -0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -3.5813    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078   -5.0114    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9635   -4.9181    3.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369   -2.8771    2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -2.9297    4.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 27  9  1  0
 26 13  1  0
 24 18  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  1
  6 47  1  1
  7 48  1  6
 10 49  1  0
 12 50  1  0
 16 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 27 57  1  0
 29 58  1  6
 30 59  1  0
 30 60  1  0
 31 61  1  0
 32 62  1  1
 33 63  1  0
 34 64  1  6
 35 65  1  0
 36 66  1  6
 37 67  1  0
 38 68  1  6
 39 69  1  0
 40 70  1  1
 41 71  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13   35                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25                                                            
CONECT   27   23   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34   18                                                            
CONECT   35   12   36                                                       
CONECT   36   35                                                            
CONECT   37   11                                                            
CONECT   38   10                                                            
CONECT   39    5                                                            
CONECT   40    4                                                            
CONECT   41    3                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

COMPND    NP0043960
HETATM    1  C1  UNL     1      -2.133  -0.741   2.492  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.527  -2.131   2.371  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.995  -2.335   1.106  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.005  -2.633   0.191  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.678  -2.323  -1.112  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.467  -1.341  -1.661  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.583  -0.171  -2.066  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.773   0.320  -1.046  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.545   0.665  -1.159  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.208   0.616  -2.351  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.580   0.978  -2.459  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.166   0.901  -3.699  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.270   1.390  -1.343  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.577   1.752  -1.344  1.00  0.00           C  
HETATM   15  O5  UNL     1       5.243   1.730  -2.408  1.00  0.00           O  
HETATM   16  C11 UNL     1       5.209   2.157  -0.164  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.507   2.190   1.007  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.121   2.608   2.285  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.376   2.644   3.440  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.937   3.026   4.645  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.276   3.378   4.673  1.00  0.00           C  
HETATM   22  O6  UNL     1       6.892   3.770   5.857  1.00  0.00           O  
HETATM   23  C17 UNL     1       7.032   3.350   3.538  1.00  0.00           C  
HETATM   24  C18 UNL     1       6.439   2.962   2.347  1.00  0.00           C  
HETATM   25  O7  UNL     1       3.241   1.833   0.974  1.00  0.00           O  
HETATM   26  C19 UNL     1       2.608   1.444  -0.124  1.00  0.00           C  
HETATM   27  C20 UNL     1       1.275   1.083  -0.068  1.00  0.00           C  
HETATM   28  O8  UNL     1      -2.397   0.895  -2.521  1.00  0.00           O  
HETATM   29  C21 UNL     1      -2.976   0.545  -3.748  1.00  0.00           C  
HETATM   30  C22 UNL     1      -3.755   1.744  -4.234  1.00  0.00           C  
HETATM   31  O9  UNL     1      -2.932   2.857  -4.410  1.00  0.00           O  
HETATM   32  C23 UNL     1      -3.966  -0.557  -3.437  1.00  0.00           C  
HETATM   33  O10 UNL     1      -4.715  -0.904  -4.568  1.00  0.00           O  
HETATM   34  C24 UNL     1      -3.196  -1.756  -2.921  1.00  0.00           C  
HETATM   35  O11 UNL     1      -4.142  -2.754  -2.701  1.00  0.00           O  
HETATM   36  C25 UNL     1      -2.457  -4.055   0.399  1.00  0.00           C  
HETATM   37  O12 UNL     1      -3.780  -4.233  -0.017  1.00  0.00           O  
HETATM   38  C26 UNL     1      -2.420  -4.435   1.870  1.00  0.00           C  
HETATM   39  O13 UNL     1      -3.523  -5.222   2.207  1.00  0.00           O  
HETATM   40  C27 UNL     1      -2.479  -3.213   2.774  1.00  0.00           C  
HETATM   41  O14 UNL     1      -2.142  -3.692   4.060  1.00  0.00           O  
HETATM   42  H1  UNL     1      -3.248  -0.797   2.521  1.00  0.00           H  
HETATM   43  H2  UNL     1      -1.723  -0.187   3.350  1.00  0.00           H  
HETATM   44  H3  UNL     1      -1.837  -0.184   1.573  1.00  0.00           H  
HETATM   45  H4  UNL     1      -0.639  -2.134   3.071  1.00  0.00           H  
HETATM   46  H5  UNL     1      -2.878  -1.971   0.465  1.00  0.00           H  
HETATM   47  H6  UNL     1      -3.235  -0.961  -0.958  1.00  0.00           H  
HETATM   48  H7  UNL     1      -0.959  -0.482  -2.937  1.00  0.00           H  
HETATM   49  H8  UNL     1       0.768   0.311  -3.283  1.00  0.00           H  
HETATM   50  H9  UNL     1       4.049   1.094  -3.992  1.00  0.00           H  
HETATM   51  H10 UNL     1       6.250   2.445  -0.182  1.00  0.00           H  
HETATM   52  H11 UNL     1       3.329   2.362   3.376  1.00  0.00           H  
HETATM   53  H12 UNL     1       4.366   3.060   5.560  1.00  0.00           H  
HETATM   54  H13 UNL     1       7.328   3.065   6.431  1.00  0.00           H  
HETATM   55  H14 UNL     1       8.092   3.623   3.524  1.00  0.00           H  
HETATM   56  H15 UNL     1       7.085   2.953   1.458  1.00  0.00           H  
HETATM   57  H16 UNL     1       0.776   1.140   0.902  1.00  0.00           H  
HETATM   58  H17 UNL     1      -2.224   0.211  -4.488  1.00  0.00           H  
HETATM   59  H18 UNL     1      -4.199   1.551  -5.248  1.00  0.00           H  
HETATM   60  H19 UNL     1      -4.603   1.997  -3.579  1.00  0.00           H  
HETATM   61  H20 UNL     1      -2.206   2.898  -3.770  1.00  0.00           H  
HETATM   62  H21 UNL     1      -4.613  -0.184  -2.619  1.00  0.00           H  
HETATM   63  H22 UNL     1      -5.283  -0.118  -4.772  1.00  0.00           H  
HETATM   64  H23 UNL     1      -2.438  -2.115  -3.635  1.00  0.00           H  
HETATM   65  H24 UNL     1      -4.953  -2.309  -2.352  1.00  0.00           H  
HETATM   66  H25 UNL     1      -1.856  -4.796  -0.152  1.00  0.00           H  
HETATM   67  H26 UNL     1      -4.410  -3.581   0.383  1.00  0.00           H  
HETATM   68  H27 UNL     1      -1.508  -5.011   2.056  1.00  0.00           H  
HETATM   69  H28 UNL     1      -3.964  -4.918   3.051  1.00  0.00           H  
HETATM   70  H29 UNL     1      -3.537  -2.877   2.857  1.00  0.00           H  
HETATM   71  H30 UNL     1      -2.195  -2.930   4.714  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3   40   45
CONECT    3    4
CONECT    4    5   36   46
CONECT    5    6
CONECT    6    7   34   47
CONECT    7    8   28   48
CONECT    8    9
CONECT    9   10   10   27
CONECT   10   11   49
CONECT   11   12   13   13
CONECT   12   50
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   16   17   17   51
CONECT   17   18   25
CONECT   18   19   19   24
CONECT   19   20   52
CONECT   20   21   21   53
CONECT   21   22   23
CONECT   22   54
CONECT   23   24   24   55
CONECT   24   56
CONECT   25   26
CONECT   26   27   27
CONECT   27   57
CONECT   28   29
CONECT   29   30   32   58
CONECT   30   31   59   60
CONECT   31   61
CONECT   32   33   34   62
CONECT   33   63
CONECT   34   35   64
CONECT   35   65
CONECT   36   37   38   66
CONECT   37   67
CONECT   38   39   40   68
CONECT   39   69
CONECT   40   41   70
CONECT   41   71
END

NP0043960
     RDKit          3D

71 75  0  0  0  0  0  0  0  0999 V2000
   -2.1333   -0.7411    2.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -2.1314    2.3711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9954   -2.3352    1.1058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047   -2.6332    0.1911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6784   -2.3227   -1.1121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4675   -1.3409   -1.6613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5830   -0.1710   -2.0661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7735    0.3195   -1.0456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5447    0.6654   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.6161   -2.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5796    0.9781   -2.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1664    0.9006   -3.6987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2702    1.3900   -1.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773    1.7522   -1.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2434    1.7299   -2.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090    2.1574   -0.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.1903    1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210    2.6081    2.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    2.6438    3.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9368    3.0258    4.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2756    3.3778    4.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920    3.7703    5.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0319    3.3499    3.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4395    2.9619    2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2409    1.8328    0.9739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    1.4437   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2748    1.0829   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966    0.8947   -2.5215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    0.5451   -3.7480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7549    1.7436   -4.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318    2.8565   -4.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655   -0.5568   -3.4371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7148   -0.9037   -4.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1956   -1.7565   -2.9212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1421   -2.7541   -2.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4571   -4.0545    0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7805   -4.2329   -0.0169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196   -4.4348    1.8701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5233   -5.2221    2.2070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788   -3.2132    2.7736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1423   -3.6923    4.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482   -0.7965    2.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226   -0.1874    3.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.1839    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -2.1342    3.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8781   -1.9714    0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2345   -0.9608   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591   -0.4822   -2.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7682    0.3109   -3.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491    1.0940   -3.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2504    2.4448   -0.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    2.3619    3.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    3.0601    5.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3281    3.0653    6.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917    3.6231    3.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0853    2.9534    1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759    1.1395    0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238    0.2110   -4.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988    1.5512   -5.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6028    1.9973   -3.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2057    2.8982   -3.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133   -0.1839   -2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2831   -0.1184   -4.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -2.1148   -3.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9532   -2.3091   -2.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8564   -4.7964   -0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095   -3.5813    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078   -5.0114    2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9635   -4.9181    3.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5369   -2.8771    2.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -2.9297    4.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 17 25  1  0
 25 26  1  0
 26 27  2  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  4 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  2  1  0
 34  6  1  0
 27  9  1  0
 26 13  1  0
 24 18  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  2 45  1  1
  4 46  1  1
  6 47  1  1
  7 48  1  6
 10 49  1  0
 12 50  1  0
 16 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 23 55  1  0
 24 56  1  0
 27 57  1  0
 29 58  1  6
 30 59  1  0
 30 60  1  0
 31 61  1  0
 32 62  1  1
 33 63  1  0
 34 64  1  6
 35 65  1  0
 36 66  1  6
 37 67  1  0
 38 68  1  6
 39 69  1  0
 40 70  1  1
 41 71  1  0
M  END

View in JSmol

Synonyms

Value	Source
7-((2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	ChEBI
Apigenin-7-O-rhamnoglucoside	ChEBI
Rhoifolin	ChEBI
Rhoifoloside	ChEBI
7-((2-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	Generator
7-((2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-benzopyran-4-one	Generator
Apigenin 7-O-b-D-rutinoside	Generator
Apigenin 7-O-β-D-rutinoside	Generator

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5187 Da

Monoisotopic Mass

578.16356 Da

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)-4H-chromen-4-one

Traditional Name

rhoifolin

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H30O14/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/h2-8,10,18,20-30,32-36H,9H2,1H3/t10-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI Key

RPMNUQRUHXIGHK-PYXJVEIZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acmella oleracea	LOTUS Database	35616633
Acorus calamus	LOTUS Database	35616633
Astragalus peregrinus	LOTUS Database	35616633
Asystasia gangetica	LOTUS Database	35616633
Asystasia gangetica L.	KNApSAcK Database	22123792
Bryum pseudotriquetrum	LOTUS Database	35616633
Carallia brachiata	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Citrus aurantium	KNApSAcK Database	22123792
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	LOTUS Database	35616633
Citrus paradisi	FooDB	PHENOL EXPLORER
Citrus sinensis	LOTUS Database	35616633
Citrus unshiu	LOTUS Database	35616633
Euchresta japonica	LOTUS Database	35616633
Gnetum africanum	LOTUS Database	35616633
Gonocaryum calleryanum	LOTUS Database	35616633
Kummerowia striata	LOTUS Database	35616633
Lawsonia alba	Plant	KNApSAcK
Lawsonia inermis	LOTUS Database	35616633
Ligustrum robustum	KNApSAcK Database	22123792
Lonicera gracilipes	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Lupinus luteus	LOTUS Database	35616633
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plagiomnium ciliare	LOTUS Database	35616633
Pyrrosia serpens	LOTUS Database	35616633
Reichardia picroides	LOTUS Database	35616633
Rhus succedanea	KNApSAcK Database	22123792
Rhus sylvestris	LOTUS Database	35616633
Serenoa repens	LOTUS Database	35616633
Syringa afghanica	KNApSAcK Database	22123792
Syringa persica	LOTUS Database	35616633
Toxicodendron succedaneum	LOTUS Database	35616633
Trachelospermum asiaticum var.intermedium	KNApSAcK Database	22123792
Trachelospermum jasminoides	LOTUS Database	35616633
Valeriana hardwickii	Plant	KNApSAcK
Vicia faba	KNApSAcK Database	22123792

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
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
Disaccharide
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:31227 )
dihydroxyflavone (CHEBI:31227 )
glycosyloxyflavone (CHEBI:31227 )
neohesperidoside (CHEBI:31227 )
flavones (C12627 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	916.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1487 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.060 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0	ALOGPS
logP	-0.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.93 m³·mol⁻¹	ChemAxon
Polarizability	56.77 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

HMDB0303149

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

APIGENIN-7-O-NEOHESPERIDOSIDE

BiGG ID

Not Available

Wikipedia Link

Rhoifolin

METLIN ID

Not Available

PubChem Compound

5282150

PDB ID

Not Available

ChEBI ID

31227

Good Scents ID

rw1698971

References

General References

Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
Wang WS, Zhou YW, Ye YH, Du N: [Studies on the flavonoids in herb from Scutellaria barbata]. Zhongguo Zhong Yao Za Zhi. 2004 Oct;29(10):957-9. [PubMed:15631081 ]
Wang X, Cheng C, Sun Q, Li F, Liu J, Zheng C: Isolation and purification of four flavonoid constituents from the flowers of Paeonia suffruticosa by high-speed counter-current chromatography. J Chromatogr A. 2005 May 20;1075(1-2):127-31. doi: 10.1016/j.chroma.2005.04.017. [PubMed:15974126 ]
Tian Y, Tang H, Wang X, Qiu F, Xue G, Li J: [Studies on antibacterial constituents of Discocleidion rufescens (2)]. Zhongguo Zhong Yao Za Zhi. 2009 Jun;34(11):1377-80. [PubMed:19771866 ]
Tao L, Huang J, Zhao Y, Li C: [Chemical constituents in Buddleja albiflora]. Zhongguo Zhong Yao Za Zhi. 2009 Dec;34(23):3043-6. [PubMed:20222420 ]

Showing NP-Card for Rhoifolin (NP0043960)

MOL for NP0043960 (Rhoifolin)

3D MOL for NP0043960 (Rhoifolin)

3D SDF for NP0043960 (Rhoifolin)

3D-SDF for NP0043960 (Rhoifolin)

PDB for NP0043960 (Rhoifolin)

3D PDB for NP0043960 (Rhoifolin)

SMILES for NP0043960 (Rhoifolin)

INCHI for NP0043960 (Rhoifolin)

Structure for NP0043960 (Rhoifolin)

3D Structure for NP0043960 (Rhoifolin)