NP-MRD: Showing NP-Card for Kaempferol 3-gentiobioside (NP0048840)

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Record Information

Version

2.0

Created at

2022-03-17 21:03:00 UTC

Updated at

2022-03-17 21:03:00 UTC

NP-MRD ID

NP0048840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kaempferol 3-gentiobioside

Description

Kaempferol 3-gentiobioside is found in Eryngium planum , Fumaria parviflora , Helichrysum arenarium, Meconopsis betonicifolia, Meconopsis grandis, Meconopsis horridula, Primula sinensis, Sauropus androgynus, Senna alata, Senna alexandrina, Sorbus pendula, Styphnolobium japonicum, Tribulus longipetalus, Tribulus pentandrus, Tribulus terrestris and Viburnum dilatum. Kaempferol 3-gentiobioside was first documented in 2000 (PMID: 10854741).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214592D          

 43 47  0  0  0  0            999 V2000
   -7.1203    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203    1.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4058    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4058    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    2.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    1.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    4.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203    0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    4.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5492    2.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203   -2.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347   -2.4290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8347   -3.2540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1202   -3.6664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4058   -3.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4058   -2.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6913   -2.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6912   -3.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1201   -4.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5491   -3.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5492   -2.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    0.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768   -0.7788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2624   -1.1913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5479   -0.7788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5479    0.0462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2624    0.4587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2624    1.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -1.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624   -2.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913   -1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334    0.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2636   -2.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 17  2  0  0  0  0
  4 18  1  0  0  0  0
 16 19  1  0  0  0  0
  2 20  1  0  0  0  0
  9 38  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 24 29  1  1  0  0  0
 23 30  1  6  0  0  0
 22 31  1  1  0  0  0
 41 27  1  0  0  0  0
 32 33  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 42  1  6  0  0  0
 35 39  1  1  0  0  0
 34 40  1  6  0  0  0
 33 41  1  1  0  0  0
 31 43  1  0  0  0  0
M  END


  Mrv0541 02241214592D          

 43 47  0  0  0  0            999 V2000
   -7.1203    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203    1.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4058    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4058    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    2.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    1.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    4.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    2.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    2.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8335    3.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203    0.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1190    4.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5492    2.9336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1203   -2.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8347   -2.4290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8347   -3.2540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1202   -3.6664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4058   -3.2539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4058   -2.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6913   -2.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6912   -3.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1201   -4.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5491   -3.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5492   -2.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9769    0.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9768   -0.7788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2624   -1.1913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5479   -0.7788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5479    0.0462    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2624    0.4587    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2624    1.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -1.1913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624   -2.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913   -1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334    0.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2636   -2.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 17  2  0  0  0  0
  4 18  1  0  0  0  0
 16 19  1  0  0  0  0
  2 20  1  0  0  0  0
  9 38  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 24 29  1  1  0  0  0
 23 30  1  6  0  0  0
 22 31  1  1  0  0  0
 41 27  1  0  0  0  0
 32 33  1  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 36 42  1  6  0  0  0
 35 39  1  1  0  0  0
 34 40  1  6  0  0  0
 33 41  1  1  0  0  0
 31 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1

> <INCHI_KEY>
BITPRCODIALMOV-DEFKTLOSSA-N

> <FORMULA>
C27H30O16

> <MOLECULAR_WEIGHT>
610.5175

> <EXACT_MASS>
610.153384912

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
57.52942839194276

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-1.6121056200000001

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.440142681458452

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.433889538519376

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648686043828816

> <JCHEM_POLAR_SURFACE_AREA>
265.52

> <JCHEM_REFRACTIVITY>
139.7079

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -13.291   5.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.625   4.706   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.625   3.166   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.291   2.396   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.957   3.166   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.957   4.706   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -10.624   5.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.624   2.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.290   3.166   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.290   4.706   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.956   5.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.623   7.786   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.956   7.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.623   4.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.289   5.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.289   7.016   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.624   0.856   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -13.291   0.856   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.955   7.786   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -15.959   5.476   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -13.291  -3.764   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -14.625  -4.534   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -14.625  -6.074   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.291  -6.844   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.957  -6.074   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.957  -4.534   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.624  -3.764   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -10.624  -6.844   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -13.291  -8.384   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -15.958  -6.844   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -15.959  -3.764   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -9.290   0.086   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -9.290  -1.454   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.956  -2.224   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.623  -1.454   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.623   0.086   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.956   0.856   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -7.956   2.396   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.289  -2.224   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -7.956  -3.764   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -10.624  -2.224   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.289   0.856   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -17.292  -4.534   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   17                                                  
CONECT    9    8   10   38                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   19                                                  
CONECT   17    8                                                            
CONECT   18    4                                                            
CONECT   19   16                                                            
CONECT   20    2                                                            
CONECT   21   22   26                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26   41                                                       
CONECT   28   25                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22   43                                                       
CONECT   32   33   37                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35   40                                                  
CONECT   35   34   36   39                                                  
CONECT   36   35   37   42                                                  
CONECT   37   32   36   38                                                  
CONECT   38    9   37                                                       
CONECT   39   35                                                            
CONECT   40   34                                                            
CONECT   41   27   33                                                       
CONECT   42   36                                                            
CONECT   43   31                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucosyl-beta-D-glucoside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucosyl-(1->6)-beta-D-glucoside	ChEBI
Kaempferol 3-O-beta-gentiobioside	ChEBI
Kaempferol 3-O-gentiobioside	ChEBI
Kaempferol beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside	ChEBI
Kaempferol beta-D-glucosyl-(1->6)-beta-D-glucoside	ChEBI
Kaempferol-3-gentiobioside	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-b-D-glucosyl-b-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-β-D-glucosyl-β-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucopyranosyl-(1->6)-b-D-glucopyranoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucosyl-(1->6)-b-D-glucoside	Generator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucosyl-(1->6)-β-D-glucoside	Generator
Kaempferol 3-O-b-gentiobioside	Generator
Kaempferol 3-O-β-gentiobioside	Generator
Kaempferol b-D-glucopyranosyl-(1->6)-b-D-glucopyranoside	Generator
Kaempferol β-D-glucopyranosyl-(1->6)-β-D-glucopyranoside	Generator
Kaempferol b-D-glucosyl-(1->6)-b-D-glucoside	Generator
Kaempferol β-D-glucosyl-(1->6)-β-D-glucoside	Generator

Chemical Formula

C₂₇H₃₀O₁₆

Average Mass

610.5175 Da

Monoisotopic Mass

610.15338 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

22149-35-5

SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1

InChI Key

BITPRCODIALMOV-DEFKTLOSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eryngium planum	Plant	KNApSAcK
Fumaria parviflora	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helichrysum arenarium	LOTUS Database	35616633
Meconopsis betonicifolia	Plant	KNApSAcK
Meconopsis grandis	Plant	KNApSAcK
Meconopsis horridula	Plant	KNApSAcK
Primula sinensis	Plant	KNApSAcK
Sauropus androgynus	LOTUS Database	35616633
Senna alata	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Sorbus pendula	Plant	KNApSAcK
Styphnolobium japonicum	Plant	KNApSAcK
Tribulus longipetalus	Plant	KNApSAcK
Tribulus pentandrus	Plant	KNApSAcK
Tribulus terrestris	Plant	KNApSAcK
Viburnum dilatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
O-glycosyl compound
Glycosyl compound
Chromone
Disaccharide
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Oxane
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.55	ALOGPS
logP	-1.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.71 m³·mol⁻¹	ChemAxon
Polarizability	57.53 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

FDB016664

KNApSAcK ID

C00005166

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-14847

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9960512

PDB ID

Not Available

ChEBI ID

136785

Good Scents ID

Not Available

References

General References

Iwashina T, Lopez-Saez JA, Herrero A, Kitajima J, Matsumoto S: Flavonol glycosides from Asplenium foreziense and its five related taxa and A. incisum. Biochem Syst Ecol. 2000 Aug 1;28(7):665-671. doi: 10.1016/s0305-1978(99)00103-9. [PubMed:10854741 ]
Moriyama H, Iizuka T, Nagai M: A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation. Yakugaku Zasshi. 2001 Nov;121(11):817-20. doi: 10.1248/yakushi.121.817. [PubMed:11725550 ]
Moriyama H, Iizuka T, Nagai M, Miyataka H, Satoh T: Antiinflammatory activity of heat-treated Cassia alata leaf extract and its flavonoid glycoside. Yakugaku Zasshi. 2003 Jul;123(7):607-11. doi: 10.1248/yakushi.123.607. [PubMed:12875244 ]
Iwashina T, Githiri SM, Benitez ER, Takemura T, Kitajima J, Takahashi R: Analysis of flavonoids in flower petals of soybean near-isogenic lines for flower and pubescence color genes. J Hered. 2007 May-Jun;98(3):250-7. doi: 10.1093/jhered/esm012. Epub 2007 Apr 9. [PubMed:17420179 ]

Showing NP-Card for Kaempferol 3-gentiobioside (NP0048840)

MOL for NP0048840 (Kaempferol 3-gentiobioside)

3D MOL for NP0048840 (Kaempferol 3-gentiobioside)

3D SDF for NP0048840 (Kaempferol 3-gentiobioside)

3D-SDF for NP0048840 (Kaempferol 3-gentiobioside)

PDB for NP0048840 (Kaempferol 3-gentiobioside)

3D PDB for NP0048840 (Kaempferol 3-gentiobioside)

SMILES for NP0048840 (Kaempferol 3-gentiobioside)

INCHI for NP0048840 (Kaempferol 3-gentiobioside)

Structure for NP0048840 (Kaempferol 3-gentiobioside)

3D Structure for NP0048840 (Kaempferol 3-gentiobioside)