NP-MRD: Showing NP-Card for Apiin (NP0043840)

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Record Information

Version

2.0

Created at

2021-06-22 17:25:14 UTC

Updated at

2021-08-20 00:00:45 UTC

NP-MRD ID

NP0043840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apiin

Description

Apiin, also known as apioside or 6''-acetylapiin, 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. Apiin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Apiin is found in Ageratina calophylla, Centaurea cyanus, Elsholtzia rugulosa, Lawsonia alba , Limonium axillare, Monarda punctata and Roman chamomile. Apiin was first documented in 2000 (PMID: 10722209). Based on a literature review a small amount of articles have been published on apiin (PMID: 15813363) (PMID: 17637182) (PMID: 18553272).

Structure

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


  Mrv1652306222119252D          

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M  END

NP0043840
     RDKit          3D

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 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  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
 14 19  1  0  0  0  0
 18 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
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 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
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 16 32  1  0  0  0  0
 10 33  1  1  0  0  0
 33 34  1  0  0  0  0
  9 35  1  6  0  0  0
  8 36  1  1  0  0  0
  3 37  1  1  0  0  0
  2 38  1  6  0  0  0
 38 39  1  0  0  0  0
  2 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0043840

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1

> <INCHI_KEY>
NTDLXWMIWOECHG-YRCFQSNFSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.59322708778055

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.17

> <JCHEM_LOGP>
-0.8378780196666665

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.741126342949714

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.297616365100709

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092569339453

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
131.7285

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apiin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043840
     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    4.5220   -3.2369    2.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112   -2.0831    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715   -1.3302    1.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898   -0.0638    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0072    0.7120    1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0060    1.9876    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1259    2.7978    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2877    2.3026    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4064    3.1193    1.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3313    1.0304    1.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1777    0.2415    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6929    0.3948    0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5758   -0.2701    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385    0.2356   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -0.4842   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    0.0955   -0.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286   -0.3683   -0.8915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2735   -0.7234   -2.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562   -0.5314   -2.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5868   -1.0688   -4.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -2.4165   -4.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    0.9276   -2.7757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3459    1.0396   -2.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2832    1.6416   -1.6331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9697    1.9204   -2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    0.6637   -0.4857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3342    0.0299   -0.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    0.2007    1.1174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9432   -0.9172    1.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -1.1514    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0747   -0.0189    1.4566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0447    0.4326    2.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7920   -0.4192    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6942   -1.4283    0.5124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313    1.0366    1.2121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9599    1.9683    2.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1660   -1.7516    0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992   -2.2773    1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859   -3.5494    1.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -1.5445    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -1.8023    2.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059    2.3977    0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1366    3.8049    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5988    3.7442    2.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2600    0.6879    2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2777   -0.7336    2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.2440   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -1.3394   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3235   -1.1458   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.5694   -4.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.9654   -4.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0628   -2.9890   -3.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173    1.4044   -3.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205    0.2430   -3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429    2.5904   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    2.2262   -2.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    1.2402    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.8401    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5403   -2.0669    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5802   -1.3612    3.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8042   -0.2002    2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1010   -0.8392   -0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3707    0.4584   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5768   -1.3074    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2573    1.5622    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346    2.1918    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838   -2.3796    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -4.0798    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  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
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 31 35  1  0
 35 36  1  0
 15 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 40  2  1  0
 11  5  1  0
 40 13  1  0
 26 17  1  0
 35 28  1  0
  3 41  1  0
  6 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 14 47  1  0
 17 48  1  1
 19 49  1  1
 20 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  6
 23 54  1  0
 24 55  1  1
 25 56  1  0
 26 57  1  1
 28 58  1  1
 30 59  1  0
 30 60  1  0
 32 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
 35 65  1  6
 36 66  1  0
 37 67  1  0
 39 68  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      -4.565  -2.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.105  -2.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.581  -0.905   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.089  -0.905   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -8.045  -0.429   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.282  -3.900   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.045  -4.818   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -7.505  -3.011   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   38   40                                             
CONECT    3    2    4   37                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   36                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23                                                            
CONECT   25   21   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28                                                            
CONECT   32   16                                                            
CONECT   33   10   34                                                       
CONECT   34   33                                                            
CONECT   35    9                                                            
CONECT   36    8                                                            
CONECT   37    3                                                            
CONECT   38    2   39                                                       
CONECT   39   38                                                            
CONECT   40    2                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

COMPND    NP0043840
HETATM    1  O1  UNL     1       4.522  -3.237   2.132  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.611  -2.083   1.664  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.771  -1.330   1.714  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.790  -0.064   1.177  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.007   0.712   1.236  1.00  0.00           C  
HETATM    6  C5  UNL     1       7.006   1.988   0.719  1.00  0.00           C  
HETATM    7  C6  UNL     1       8.126   2.798   0.728  1.00  0.00           C  
HETATM    8  C7  UNL     1       9.288   2.303   1.278  1.00  0.00           C  
HETATM    9  O2  UNL     1      10.406   3.119   1.285  1.00  0.00           O  
HETATM   10  C8  UNL     1       9.331   1.030   1.806  1.00  0.00           C  
HETATM   11  C9  UNL     1       8.178   0.241   1.779  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.693   0.395   0.628  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.576  -0.270   0.555  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.439   0.236  -0.026  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.236  -0.484  -0.102  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.162   0.096  -0.697  1.00  0.00           O  
HETATM   17  C13 UNL     1      -1.129  -0.368  -0.891  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.274  -0.723  -2.259  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.556  -0.531  -2.709  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.587  -1.069  -4.146  1.00  0.00           C  
HETATM   21  O6  UNL     1      -2.248  -2.417  -4.107  1.00  0.00           O  
HETATM   22  C16 UNL     1      -2.961   0.928  -2.776  1.00  0.00           C  
HETATM   23  O7  UNL     1      -4.346   1.040  -2.741  1.00  0.00           O  
HETATM   24  C17 UNL     1      -2.283   1.642  -1.633  1.00  0.00           C  
HETATM   25  O8  UNL     1      -0.970   1.920  -2.048  1.00  0.00           O  
HETATM   26  C18 UNL     1      -2.174   0.664  -0.486  1.00  0.00           C  
HETATM   27  O9  UNL     1      -3.334   0.030  -0.174  1.00  0.00           O  
HETATM   28  C19 UNL     1      -3.780   0.201   1.117  1.00  0.00           C  
HETATM   29  O10 UNL     1      -3.943  -0.917   1.871  1.00  0.00           O  
HETATM   30  C20 UNL     1      -5.285  -1.151   2.047  1.00  0.00           C  
HETATM   31  C21 UNL     1      -6.075  -0.019   1.457  1.00  0.00           C  
HETATM   32  O11 UNL     1      -7.045   0.433   2.366  1.00  0.00           O  
HETATM   33  C22 UNL     1      -6.792  -0.419   0.187  1.00  0.00           C  
HETATM   34  O12 UNL     1      -7.694  -1.428   0.512  1.00  0.00           O  
HETATM   35  C23 UNL     1      -5.031   1.037   1.212  1.00  0.00           C  
HETATM   36  O13 UNL     1      -4.960   1.968   2.248  1.00  0.00           O  
HETATM   37  C24 UNL     1       1.166  -1.752   0.419  1.00  0.00           C  
HETATM   38  C25 UNL     1       2.299  -2.277   1.007  1.00  0.00           C  
HETATM   39  O14 UNL     1       2.286  -3.549   1.547  1.00  0.00           O  
HETATM   40  C26 UNL     1       3.494  -1.544   1.075  1.00  0.00           C  
HETATM   41  H1  UNL     1       6.622  -1.802   2.188  1.00  0.00           H  
HETATM   42  H2  UNL     1       6.106   2.398   0.282  1.00  0.00           H  
HETATM   43  H3  UNL     1       8.137   3.805   0.324  1.00  0.00           H  
HETATM   44  H4  UNL     1      10.599   3.744   2.061  1.00  0.00           H  
HETATM   45  H5  UNL     1      10.260   0.688   2.223  1.00  0.00           H  
HETATM   46  H6  UNL     1       8.278  -0.734   2.203  1.00  0.00           H  
HETATM   47  H7  UNL     1       2.503   1.244  -0.438  1.00  0.00           H  
HETATM   48  H8  UNL     1      -1.250  -1.339  -0.367  1.00  0.00           H  
HETATM   49  H9  UNL     1      -3.324  -1.146  -2.169  1.00  0.00           H  
HETATM   50  H10 UNL     1      -1.786  -0.569  -4.766  1.00  0.00           H  
HETATM   51  H11 UNL     1      -3.576  -0.965  -4.606  1.00  0.00           H  
HETATM   52  H12 UNL     1      -3.063  -2.989  -3.961  1.00  0.00           H  
HETATM   53  H13 UNL     1      -2.617   1.404  -3.735  1.00  0.00           H  
HETATM   54  H14 UNL     1      -4.821   0.243  -3.058  1.00  0.00           H  
HETATM   55  H15 UNL     1      -2.743   2.590  -1.356  1.00  0.00           H  
HETATM   56  H16 UNL     1      -0.969   2.226  -2.982  1.00  0.00           H  
HETATM   57  H17 UNL     1      -1.741   1.240   0.368  1.00  0.00           H  
HETATM   58  H18 UNL     1      -2.984   0.840   1.613  1.00  0.00           H  
HETATM   59  H19 UNL     1      -5.540  -2.067   1.435  1.00  0.00           H  
HETATM   60  H20 UNL     1      -5.580  -1.361   3.104  1.00  0.00           H  
HETATM   61  H21 UNL     1      -7.804  -0.200   2.305  1.00  0.00           H  
HETATM   62  H22 UNL     1      -6.101  -0.839  -0.563  1.00  0.00           H  
HETATM   63  H23 UNL     1      -7.371   0.458  -0.158  1.00  0.00           H  
HETATM   64  H24 UNL     1      -8.577  -1.307   0.099  1.00  0.00           H  
HETATM   65  H25 UNL     1      -5.257   1.562   0.254  1.00  0.00           H  
HETATM   66  H26 UNL     1      -4.035   2.192   2.492  1.00  0.00           H  
HETATM   67  H27 UNL     1       0.284  -2.380   0.407  1.00  0.00           H  
HETATM   68  H28 UNL     1       1.429  -4.080   1.498  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   40
CONECT    3    4    4   41
CONECT    4    5   12
CONECT    5    6    6   11
CONECT    6    7   42
CONECT    7    8    8   43
CONECT    8    9   10
CONECT    9   44
CONECT   10   11   11   45
CONECT   11   46
CONECT   12   13
CONECT   13   14   14   40
CONECT   14   15   47
CONECT   15   16   37   37
CONECT   16   17
CONECT   17   18   26   48
CONECT   18   19
CONECT   19   20   22   49
CONECT   20   21   50   51
CONECT   21   52
CONECT   22   23   24   53
CONECT   23   54
CONECT   24   25   26   55
CONECT   25   56
CONECT   26   27   57
CONECT   27   28
CONECT   28   29   35   58
CONECT   29   30
CONECT   30   31   59   60
CONECT   31   32   33   35
CONECT   32   61
CONECT   33   34   62   63
CONECT   34   64
CONECT   35   36   65
CONECT   36   66
CONECT   37   38   67
CONECT   38   39   40   40
CONECT   39   68
END

NP0043840
     RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
    4.5220   -3.2369    2.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112   -2.0831    1.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715   -1.3302    1.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898   -0.0638    1.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0072    0.7120    1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0060    1.9876    0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1259    2.7978    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2877    2.3026    1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4064    3.1193    1.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3313    1.0304    1.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1777    0.2415    1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6929    0.3948    0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5758   -0.2701    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4385    0.2356   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2356   -0.4842   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623    0.0955   -0.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286   -0.3683   -0.8915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2735   -0.7234   -2.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5562   -0.5314   -2.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5868   -1.0688   -4.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476   -2.4165   -4.1068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9607    0.9276   -2.7757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3459    1.0396   -2.7407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2832    1.6416   -1.6331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9697    1.9204   -2.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739    0.6637   -0.4857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3342    0.0299   -0.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7799    0.2007    1.1174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9432   -0.9172    1.8705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2850   -1.1514    2.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0747   -0.0189    1.4566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0447    0.4326    2.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7920   -0.4192    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6942   -1.4283    0.5124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313    1.0366    1.2121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9599    1.9683    2.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1660   -1.7516    0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992   -2.2773    1.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859   -3.5494    1.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -1.5445    1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -1.8023    2.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1059    2.3977    0.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1366    3.8049    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5988    3.7442    2.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2600    0.6879    2.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2777   -0.7336    2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5030    1.2440   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -1.3394   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3235   -1.1458   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.5694   -4.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.9654   -4.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0628   -2.9890   -3.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173    1.4044   -3.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8205    0.2430   -3.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7429    2.5904   -1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686    2.2262   -2.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7413    1.2402    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9843    0.8401    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5403   -2.0669    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5802   -1.3612    3.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8042   -0.2002    2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1010   -0.8392   -0.5625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3707    0.4584   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5768   -1.3074    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2573    1.5622    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0346    2.1918    2.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838   -2.3796    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -4.0798    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  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
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 31 35  1  0
 35 36  1  0
 15 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  2  0
 40  2  1  0
 11  5  1  0
 40 13  1  0
 26 17  1  0
 35 28  1  0
  3 41  1  0
  6 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 14 47  1  0
 17 48  1  1
 19 49  1  1
 20 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  6
 23 54  1  0
 24 55  1  1
 25 56  1  0
 26 57  1  1
 28 58  1  1
 30 59  1  0
 30 60  1  0
 32 61  1  0
 33 62  1  0
 33 63  1  0
 34 64  1  0
 35 65  1  6
 36 66  1  0
 37 67  1  0
 39 68  1  0
M  END

View in JSmol

Synonyms

Value	Source
5,7,4'-Trihydroxyflavone 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]	ChEBI
7-((2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone	ChEBI
7-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one	ChEBI
7-O-(beta-D-Apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4'-trihydroxyflavone	ChEBI
Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]	ChEBI
Apioside	ChEBI
5,7,4'-Trihydroxyflavone 7-O-[b-D-apiosyl-(1->2)-b-D-glucoside]	Generator
5,7,4'-Trihydroxyflavone 7-O-[β-D-apiosyl-(1->2)-β-D-glucoside]	Generator
7-((2-O-b-D-Apiofuranosyl-b-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone	Generator
7-((2-O-Β-D-apiofuranosyl-β-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone	Generator
7-[(2-O-D-Apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one	Generator
7-[(2-O-D-Apio-β-D-furanosyl-β-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one	Generator
7-O-(b-D-Apiofuranosyl-1,2-b-D-glucosyl)-5,7,4'-trihydroxyflavone	Generator
7-O-(Β-D-apiofuranosyl-1,2-β-D-glucosyl)-5,7,4'-trihydroxyflavone	Generator
Apigenin 7-O-[b-D-apiosyl-(1->2)-b-D-glucoside]	Generator
Apigenin 7-O-[β-D-apiosyl-(1->2)-β-D-glucoside]	Generator
6''-Acetylapiin	MeSH
Apiin	MeSH

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

apiin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1

InChI Key

NTDLXWMIWOECHG-YRCFQSNFSA-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
Ageratina calophylla	LOTUS Database	35616633
Anthemis nobilis	KNApSAcK Database	22123792
Anthriscus cerefolium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens	KNApSAcK Database	22123792
Apium graveolens var. secalinum	FooDB	PHENOL EXPLORER
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Centaurea cyanus	LOTUS Database	35616633
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Crotalaria micans	KNApSAcK Database	22123792
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Elsholtzia rugulosa	LOTUS Database	35616633
Lawsonia alba	Plant	KNApSAcK
Lens culinaris	FooDB	PHENOL EXPLORER
Limonium axillare	LOTUS Database	35616633
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Monarda punctata	LOTUS Database	35616633
Petroselinum crispum	KNApSAcK Database	22123792
Roman chamomile	-	KNApSAcK
Vicia balansae	KNApSAcK Database	22123792
Vicia hirsuta	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
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Benzenoid
Oxane
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:15932 )
dihydroxyflavone (CHEBI:15932 )
glycosyloxyflavone (CHEBI:15932 )
flavones (C04858 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	942.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3889 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.720 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-0.17	ALOGPS
logP	-0.84	ChemAxon
logS	-2.6	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	7	ChemAxon
Refractivity	131.73 m³·mol⁻¹	ChemAxon
Polarizability	55.59 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001019

Chemspider ID

4444321

KEGG Compound ID

C04858

BioCyc ID

7-O-BETA-D-APIOFURANOSYL-12-BETA-D-GLU

BiGG ID

Not Available

Wikipedia Link

Apiin

METLIN ID

Not Available

PubChem Compound

5280746

PDB ID

Not Available

ChEBI ID

15932

Good Scents ID

rw1588401

References

General References

Fejes S, Blazovics A, Lugasi A, Lemberkovics E, Petri G, Kery A: In vitro antioxidant activity of Anthriscus cerefolium L. (Hoffm.) extracts. J Ethnopharmacol. 2000 Mar;69(3):259-65. doi: 10.1016/s0378-8741(99)00171-3. [PubMed:10722209 ]
Mikhaeil BR, Badria FA, Maatooq GT, Amer MM: Antioxidant and immunomodulatory constituents of henna leaves. Z Naturforsch C J Biosci. 2004 Jul-Aug;59(7-8):468-76. doi: 10.1515/znc-2004-7-803. [PubMed:15813363 ]
Mencherini T, Cau A, Bianco G, Della Loggia R, Aquino RP, Autore G: An extract of Apium graveolens var. dulce leaves: structure of the major constituent, apiin, and its anti-inflammatory properties. J Pharm Pharmacol. 2007 Jun;59(6):891-7. doi: 10.1211/jpp.59.6.0016. [PubMed:17637182 ]
Liu AL, Liu B, Qin HL, Lee SM, Wang YT, Du GH: Anti-influenza virus activities of flavonoids from the medicinal plant Elsholtzia rugulosa. Planta Med. 2008 Jun;74(8):847-51. doi: 10.1055/s-2008-1074558. Epub 2008 Jun 13. [PubMed:18553272 ]

Showing NP-Card for Apiin (NP0043840)

MOL for NP0043840 (Apiin)

3D MOL for NP0043840 (Apiin)

3D SDF for NP0043840 (Apiin)

3D-SDF for NP0043840 (Apiin)

PDB for NP0043840 (Apiin)

3D PDB for NP0043840 (Apiin)

SMILES for NP0043840 (Apiin)

INCHI for NP0043840 (Apiin)

Structure for NP0043840 (Apiin)

3D Structure for NP0043840 (Apiin)