NP-MRD: Showing NP-Card for Icariin (NP0043901)

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Record Information

Version

1.0

Created at

2021-06-22 17:28:16 UTC

Updated at

2024-04-19 09:50:47 UTC

NP-MRD ID

NP0043901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Icariin

Description

Icariin, also known as ieariline, 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. Thus, icariin is considered to be a flavonoid. Icariin is found in Campanula medium, Epimedium acuminatum, Epimedium diphyllum, Epimedium grandiflorum, Epimedium hunanense, Epimedium pubescens, Epimedium sagittatum, Epimedium sempervirens, Epimedium sutchuenense and Epimedium wushanense. It was first documented in 2005 (PMID: 16380159). Based on a literature review a significant number of articles have been published on Icariin (PMID: 20026390) (PMID: 16751992) (PMID: 17120748) (PMID: 17142971).

Structure

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


  Mrv1652306222119282D          

 48 52  0  0  1  0            999 V2000
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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  9 14  1  0  0  0  0
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 44 45  1  0  0  0  0
  5 46  1  6  0  0  0
  4 47  1  6  0  0  0
  3 48  1  1  0  0  0
M  END

NP0043901
     RDKit          3D

 88 92  0  0  0  0  0  0  0  0999 V2000
   -5.9988    5.3581    1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    3.9436    1.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    3.1357    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    1.7624    1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804    0.8744    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7770    1.9997    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3422    3.3230   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8012    3.4749   -1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7349   -1.6034    0.4348 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9399   -3.0849    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8249   -3.4140    1.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
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 48 88  1  0
M  END


  Mrv1652306222119282D          

 48 52  0  0  1  0            999 V2000
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    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  2  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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 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
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 25  1  0  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 29 34  1  6  0  0  0
 28 35  1  1  0  0  0
 27 36  1  6  0  0  0
 16 37  1  0  0  0  0
 10 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  0  0  0  0
  5 46  1  6  0  0  0
  4 47  1  6  0  0  0
  3 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0043901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C(=O)C2=C(O1)C(CC=C(C)C)=C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

> <INCHI_KEY>
TZJALUIVHRYQQB-XLRXWWTNSA-N

> <FORMULA>
C33H40O15

> <MOLECULAR_WEIGHT>
676.668

> <EXACT_MASS>
676.236720588

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
68.52372435210071

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
0.8120329543333347

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.905637787860833

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.0685466559563865

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092344940455

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
166.62039999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
icariin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043901
     RDKit          3D

 88 92  0  0  0  0  0  0  0  0999 V2000
   -5.9988    5.3581    1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    3.9436    1.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2804    0.8744    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7770    1.9997    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5085    2.6911   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422    3.3230   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0671    3.6253   -0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9493   -3.3364    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2009   -3.6155   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0431   -4.0493    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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 43 83  1  6
 44 84  1  0
 45 85  1  1
 46 86  1  0
 47 87  1  0
 48 88  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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   48                                                  
CONECT    4    3    5   47                                                  
CONECT    5    4    6   46                                                  
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                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   18   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29                                                            
CONECT   35   28                                                            
CONECT   36   27                                                            
CONECT   37   16                                                            
CONECT   38   10   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42   38                                                       
CONECT   44   41   45                                                       
CONECT   45   44                                                            
CONECT   46    5                                                            
CONECT   47    4                                                            
CONECT   48    3                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

COMPND    NP0043901
HETATM    1  C1  UNL     1      -5.999   5.358   1.564  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.132   3.944   1.754  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.043   3.136   1.471  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.281   1.762   1.670  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.280   0.874   1.417  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.014   1.260   0.963  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.016   0.278   0.606  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.751   0.741   0.646  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.274   0.013   0.360  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.553   0.535   0.431  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.777   2.000   0.697  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.508   2.691  -0.582  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.342   3.323  -1.357  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.806   3.950  -2.626  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.801   3.475  -1.138  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.673  -0.214   0.157  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.876   0.360   0.268  1.00  0.00           O  
HETATM   18  C15 UNL     1       5.176  -0.034   0.049  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.450  -1.208   0.872  1.00  0.00           O  
HETATM   20  C16 UNL     1       6.735  -1.603   0.435  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.940  -3.085   0.601  1.00  0.00           C  
HETATM   22  O5  UNL     1       6.825  -3.414   1.942  1.00  0.00           O  
HETATM   23  C18 UNL     1       7.703  -0.797   1.273  1.00  0.00           C  
HETATM   24  O6  UNL     1       8.970  -0.812   0.717  1.00  0.00           O  
HETATM   25  C19 UNL     1       7.161   0.609   1.483  1.00  0.00           C  
HETATM   26  O7  UNL     1       6.490   0.720   2.684  1.00  0.00           O  
HETATM   27  C20 UNL     1       6.212   0.981   0.355  1.00  0.00           C  
HETATM   28  O8  UNL     1       7.006   1.312  -0.744  1.00  0.00           O  
HETATM   29  C21 UNL     1       2.477  -1.515  -0.206  1.00  0.00           C  
HETATM   30  C22 UNL     1       1.190  -2.120  -0.310  1.00  0.00           C  
HETATM   31  O9  UNL     1       1.114  -3.426  -0.691  1.00  0.00           O  
HETATM   32  C23 UNL     1       0.107  -1.314  -0.013  1.00  0.00           C  
HETATM   33  C24 UNL     1      -1.184  -1.809  -0.064  1.00  0.00           C  
HETATM   34  O10 UNL     1      -1.391  -2.996  -0.397  1.00  0.00           O  
HETATM   35  C25 UNL     1      -2.294  -0.997   0.255  1.00  0.00           C  
HETATM   36  O11 UNL     1      -3.548  -1.579   0.179  1.00  0.00           O  
HETATM   37  C26 UNL     1      -4.461  -1.503  -0.871  1.00  0.00           C  
HETATM   38  O12 UNL     1      -5.748  -1.465  -0.317  1.00  0.00           O  
HETATM   39  C27 UNL     1      -6.211  -2.749  -0.047  1.00  0.00           C  
HETATM   40  C28 UNL     1      -7.267  -2.801   1.027  1.00  0.00           C  
HETATM   41  C29 UNL     1      -6.575  -3.531  -1.265  1.00  0.00           C  
HETATM   42  O13 UNL     1      -6.283  -4.890  -1.025  1.00  0.00           O  
HETATM   43  C30 UNL     1      -5.696  -3.014  -2.412  1.00  0.00           C  
HETATM   44  O14 UNL     1      -6.256  -1.924  -3.056  1.00  0.00           O  
HETATM   45  C31 UNL     1      -4.341  -2.680  -1.807  1.00  0.00           C  
HETATM   46  O15 UNL     1      -3.553  -2.271  -2.896  1.00  0.00           O  
HETATM   47  C32 UNL     1      -2.784   2.617   0.771  1.00  0.00           C  
HETATM   48  C33 UNL     1      -3.839   3.520   1.042  1.00  0.00           C  
HETATM   49  H1  UNL     1      -5.667   5.459   0.503  1.00  0.00           H  
HETATM   50  H2  UNL     1      -5.188   5.737   2.206  1.00  0.00           H  
HETATM   51  H3  UNL     1      -6.905   5.929   1.778  1.00  0.00           H  
HETATM   52  H4  UNL     1      -6.240   1.444   2.004  1.00  0.00           H  
HETATM   53  H5  UNL     1      -4.473  -0.159   1.619  1.00  0.00           H  
HETATM   54  H6  UNL     1       2.774   2.236   1.076  1.00  0.00           H  
HETATM   55  H7  UNL     1       1.041   2.339   1.486  1.00  0.00           H  
HETATM   56  H8  UNL     1       0.443   2.653  -0.894  1.00  0.00           H  
HETATM   57  H9  UNL     1       0.859   3.470  -2.953  1.00  0.00           H  
HETATM   58  H10 UNL     1       2.586   3.769  -3.413  1.00  0.00           H  
HETATM   59  H11 UNL     1       1.736   5.032  -2.447  1.00  0.00           H  
HETATM   60  H12 UNL     1       4.302   2.571  -1.579  1.00  0.00           H  
HETATM   61  H13 UNL     1       4.067   3.625  -0.089  1.00  0.00           H  
HETATM   62  H14 UNL     1       4.186   4.383  -1.678  1.00  0.00           H  
HETATM   63  H15 UNL     1       5.298  -0.475  -0.952  1.00  0.00           H  
HETATM   64  H16 UNL     1       6.838  -1.317  -0.621  1.00  0.00           H  
HETATM   65  H17 UNL     1       7.949  -3.336   0.226  1.00  0.00           H  
HETATM   66  H18 UNL     1       6.201  -3.616  -0.052  1.00  0.00           H  
HETATM   67  H19 UNL     1       6.043  -4.049   2.012  1.00  0.00           H  
HETATM   68  H20 UNL     1       7.756  -1.281   2.269  1.00  0.00           H  
HETATM   69  H21 UNL     1       9.640  -0.387   1.303  1.00  0.00           H  
HETATM   70  H22 UNL     1       8.024   1.296   1.441  1.00  0.00           H  
HETATM   71  H23 UNL     1       6.893   1.436   3.222  1.00  0.00           H  
HETATM   72  H24 UNL     1       5.711   1.932   0.732  1.00  0.00           H  
HETATM   73  H25 UNL     1       7.415   2.226  -0.627  1.00  0.00           H  
HETATM   74  H26 UNL     1       3.299  -2.179  -0.440  1.00  0.00           H  
HETATM   75  H27 UNL     1       0.360  -3.999  -0.834  1.00  0.00           H  
HETATM   76  H28 UNL     1      -4.233  -0.570  -1.425  1.00  0.00           H  
HETATM   77  H29 UNL     1      -5.317  -3.282   0.396  1.00  0.00           H  
HETATM   78  H30 UNL     1      -6.758  -2.751   2.021  1.00  0.00           H  
HETATM   79  H31 UNL     1      -8.017  -1.991   0.971  1.00  0.00           H  
HETATM   80  H32 UNL     1      -7.764  -3.815   0.965  1.00  0.00           H  
HETATM   81  H33 UNL     1      -7.644  -3.407  -1.572  1.00  0.00           H  
HETATM   82  H34 UNL     1      -5.521  -5.150  -1.603  1.00  0.00           H  
HETATM   83  H35 UNL     1      -5.529  -3.848  -3.131  1.00  0.00           H  
HETATM   84  H36 UNL     1      -7.221  -1.975  -3.145  1.00  0.00           H  
HETATM   85  H37 UNL     1      -3.856  -3.526  -1.322  1.00  0.00           H  
HETATM   86  H38 UNL     1      -2.817  -1.685  -2.623  1.00  0.00           H  
HETATM   87  H39 UNL     1      -1.847   2.960   0.432  1.00  0.00           H  
HETATM   88  H40 UNL     1      -3.641   4.596   0.873  1.00  0.00           H  
CONECT    1    2   49   50   51
CONECT    2    3
CONECT    3    4    4   48
CONECT    4    5   52
CONECT    5    6    6   53
CONECT    6    7   47
CONECT    7    8   35   35
CONECT    8    9
CONECT    9   10   10   32
CONECT   10   11   16
CONECT   11   12   54   55
CONECT   12   13   13   56
CONECT   13   14   15
CONECT   14   57   58   59
CONECT   15   60   61   62
CONECT   16   17   29   29
CONECT   17   18
CONECT   18   19   27   63
CONECT   19   20
CONECT   20   21   23   64
CONECT   21   22   65   66
CONECT   22   67
CONECT   23   24   25   68
CONECT   24   69
CONECT   25   26   27   70
CONECT   26   71
CONECT   27   28   72
CONECT   28   73
CONECT   29   30   74
CONECT   30   31   32   32
CONECT   31   75
CONECT   32   33
CONECT   33   34   34   35
CONECT   35   36
CONECT   36   37
CONECT   37   38   45   76
CONECT   38   39
CONECT   39   40   41   77
CONECT   40   78   79   80
CONECT   41   42   43   81
CONECT   42   82
CONECT   43   44   45   83
CONECT   44   84
CONECT   45   46   85
CONECT   46   86
CONECT   47   48   48   87
CONECT   48   88
END

NP0043901
     RDKit          3D

88 92  0  0  0  0  0  0  0  0999 V2000
   -5.9988    5.3581    1.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    3.9436    1.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    3.1357    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    1.7624    1.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2804    0.8744    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    1.2601    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    0.2776    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507    0.7412    0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2743    0.0133    0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5530    0.5346    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    1.9997    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5085    2.6911   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422    3.3230   -1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063    3.9495   -2.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012    3.4749   -1.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6726   -0.2144    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.3603    0.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1755   -0.0335    0.0494 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4498   -1.2084    0.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7349   -1.6034    0.4348 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9399   -3.0849    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8249   -3.4140    1.9420 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025   -0.7971    1.2731 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9696   -0.8115    0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1610    0.6085    1.4834 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4904    0.7204    2.6837 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2115    0.9810    0.3554 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0058    1.3118   -0.7438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -1.5155   -0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896   -2.1198   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1137   -3.4257   -0.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1072   -1.3138   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1839   -1.8093   -0.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905   -2.9964   -0.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936   -0.9971    0.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5476   -1.5788    0.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4610   -1.5031   -0.8713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7479   -1.4655   -0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2110   -2.7487   -0.0473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2672   -2.8011    1.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5747   -3.5310   -1.2651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2826   -4.8897   -1.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6965   -3.0139   -2.4118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2557   -1.9244   -3.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3412   -2.6801   -1.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5532   -2.2709   -2.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838    2.6167    0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8390    3.5198    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6673    5.4589    0.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1881    5.7372    2.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9050    5.9286    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2399    1.4435    2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -0.1590    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7740    2.2363    1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415    2.3391    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    2.6527   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587    3.4696   -2.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5857    3.7693   -3.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7360    5.0318   -2.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    2.5714   -1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671    3.6253   -0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    4.3828   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2982   -0.4746   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8376   -1.3170   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9493   -3.3364    0.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2009   -3.6155   -0.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0431   -4.0493    2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7558   -1.2815    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6399   -0.3869    1.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0235    1.2957    1.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8926    1.4362    3.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7108    1.9317    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4148    2.2264   -0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987   -2.1790   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596   -3.9986   -0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332   -0.5699   -1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3168   -3.2820    0.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582   -2.7509    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0173   -1.9910    0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7635   -3.8153    0.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6435   -3.4074   -1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5211   -5.1496   -1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5290   -3.8484   -3.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2209   -1.9747   -3.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564   -3.5263   -1.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8174   -1.6848   -2.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471    2.9595    0.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6410    4.5960    0.8731 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
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 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
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  1  0
 45 46  1  0
  6 47  1  0
 47 48  2  0
 48  3  1  0
 35  7  2  0
 45 37  1  0
 32  9  1  0
 27 18  1  0
  1 49  1  0
  1 50  1  0
  1 51  1  0
  4 52  1  0
  5 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  0
 14 57  1  0
 14 58  1  0
 14 59  1  0
 15 60  1  0
 15 61  1  0
 15 62  1  0
 18 63  1  6
 20 64  1  6
 21 65  1  0
 21 66  1  0
 22 67  1  0
 23 68  1  1
 24 69  1  0
 25 70  1  1
 26 71  1  0
 27 72  1  1
 28 73  1  0
 29 74  1  0
 31 75  1  0
 37 76  1  6
 39 77  1  1
 40 78  1  0
 40 79  1  0
 40 80  1  0
 41 81  1  6
 42 82  1  0
 43 83  1  6
 44 84  1  0
 45 85  1  1
 46 86  1  0
 47 87  1  0
 48 88  1  0
M  END

View in JSmol

Synonyms

Value	Source
Ieariline	ChEBI
3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	MeSH

Chemical Formula

C₃₃H₄₀O₁₅

Average Mass

676.6680 Da

Monoisotopic Mass

676.23672 Da

IUPAC Name

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

icariin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)C(=O)C2=C(O1)C(CC=C(C)C)=C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2O

InChI Identifier

InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1

InChI Key

TZJALUIVHRYQQB-XLRXWWTNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Campanula medium	LOTUS Database	35616633
Epimedium acuminatum	LOTUS Database	35616633
Epimedium diphyllum	LOTUS Database	35616633
Epimedium grandiflorum	LOTUS Database	35616633
Epimedium hunanense	LOTUS Database	35616633
Epimedium pubescens	LOTUS Database	35616633
Epimedium sagittatum	Linigton's dataset	20026390
Epimedium sempervirens	LOTUS Database	35616633
Epimedium spp.	KNApSAcK Database	22123792
Epimedium sutchuenense	LOTUS Database	35616633
Epimedium wushanense	LOTUS Database	35616633
Vancouveria hexandra	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

8-prenylated flavone
Flavonoid-3-o-glycoside
Flavonoid-7-o-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
Methoxybenzene
Phenol ether
Phenoxy compound
Anisole
Alkyl aryl ether
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glycosyloxyflavone (CHEBI:78420 )
flavonols (CHEBI:78420 )
Flavones and Flavonols (C17555 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	948.48 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	76.85 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.736 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	0.81	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-3	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	9	ChemAxon
Refractivity	166.62 m³·mol⁻¹	ChemAxon
Polarizability	68.52 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

Not Available

DrugBank ID

DB12052

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005824

Chemspider ID

4477421

KEGG Compound ID

C17555

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Icariin

METLIN ID

Not Available

PubChem Compound

5318997

PDB ID

Not Available

ChEBI ID

78420

Good Scents ID

rw1665411

References

General References

Xia Q, Xu D, Huang Z, Liu J, Wang X, Wang X, Liu S: Preparation of icariside II from icariin by enzymatic hydrolysis method. Fitoterapia. 2010 Jul;81(5):437-42. doi: 10.1016/j.fitote.2009.12.006. Epub 2009 Dec 22. [PubMed:20026390 ]
Pan Y, Kong L, Xia X, Zhang W, Xia Z, Jiang F: Antidepressant-like effect of icariin and its possible mechanism in mice. Pharmacol Biochem Behav. 2005 Dec;82(4):686-94. doi: 10.1016/j.pbb.2005.11.010. Epub 2005 Dec 27. [PubMed:16380159 ]
Zhang ZB, Yang QT: The testosterone mimetic properties of icariin. Asian J Androl. 2006 Sep;8(5):601-5. doi: 10.1111/j.1745-7262.2006.00197.x. Epub 2006 Jun 5. [PubMed:16751992 ]
Jiang Z, Hu B, Wang J, Tang Q, Tan Y, Xiang J, Liu J: Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum. J Huazhong Univ Sci Technolog Med Sci. 2006;26(4):460-2. doi: 10.1007/s11596-006-0421-y. [PubMed:17120748 ]
Pan Y, Zhang WY, Xia X, Kong LD: Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats. Biol Pharm Bull. 2006 Dec;29(12):2399-403. doi: 10.1248/bpb.29.2399. [PubMed:17142971 ]

Showing NP-Card for Icariin (NP0043901)

MOL for NP0043901 (Icariin)

3D MOL for NP0043901 (Icariin)

3D SDF for NP0043901 (Icariin)

3D-SDF for NP0043901 (Icariin)

PDB for NP0043901 (Icariin)

3D PDB for NP0043901 (Icariin)

SMILES for NP0043901 (Icariin)

INCHI for NP0043901 (Icariin)

Structure for NP0043901 (Icariin)

3D Structure for NP0043901 (Icariin)