NP-MRD: Showing NP-Card for Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside (NP0045756)

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Record Information

Version

2.0

Created at

2022-03-17 19:36:54 UTC

Updated at

2022-03-17 19:36:54 UTC

NP-MRD ID

NP0045756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside

Description

Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212172D          

 51 57  0  0  0  0            999 V2000
   -4.4837    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    1.6124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3403    2.4374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6258    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    4.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    3.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    3.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176    4.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    0.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    1.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    0.3749    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6258   -1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -2.1002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9465    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -2.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -3.3376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1969   -3.7501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5176   -3.3376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5176   -2.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1969   -2.1001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1969   -1.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2320   -2.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -3.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969   -4.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321   -3.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -4.5751    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
  4 17  1  0  0  0  0
  5 39  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  7  9  1  0  0  0  0
 39  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 18  1  0  0  0  0
  8 19  1  1  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 26 25  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 32 30  2  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 31 35  2  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 21 36  1  0  0  0  0
 23 37  1  0  0  0  0
 28 46  1  0  0  0  0
 35 38  1  0  0  0  0
 20 39  1  6  0  0  0
 40 41  1  0  0  0  0
 40 45  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 44 47  1  6  0  0  0
 41 48  1  1  0  0  0
 42 49  1  6  0  0  0
 43 50  1  1  0  0  0
 48 51  1  0  0  0  0
M  CHG  1  26   1
M  END


  Mrv0541 02241212172D          

 51 57  0  0  0  0            999 V2000
   -4.4837    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    1.6124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3403    2.4374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6258    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    4.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    3.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113    2.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    3.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176    4.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4837    0.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9126    2.8499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    1.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7692   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258    0.3749    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.6258   -1.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -0.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9113   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176    1.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5176   -0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321    0.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712    0.1097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -2.1002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9465    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547    1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -2.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114   -3.3376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1969   -3.7501    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5176   -3.3376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5176   -2.5126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1969   -2.1001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1969   -1.2751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2320   -2.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -3.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1969   -4.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321   -3.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6258   -4.5751    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
  4 17  1  0  0  0  0
  5 39  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  7  9  1  0  0  0  0
 39  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 18  1  0  0  0  0
  8 19  1  1  0  0  0
 20 21  1  0  0  0  0
 20 25  2  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 26 25  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 32 30  2  0  0  0  0
 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 31 35  2  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 21 36  1  0  0  0  0
 23 37  1  0  0  0  0
 28 46  1  0  0  0  0
 35 38  1  0  0  0  0
 20 39  1  6  0  0  0
 40 41  1  0  0  0  0
 40 45  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 44 47  1  6  0  0  0
 41 48  1  1  0  0  0
 42 49  1  6  0  0  0
 43 50  1  1  0  0  0
 48 51  1  0  0  0  0
M  CHG  1  26   1
M  END
> <DATABASE_ID>
NP0045756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C(C4[C@H](O)[C@H](OC5=C4C(O)=CC(O)=C5)C4=CC=C(O)C=C4)=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H32O15/c37-13-25-29(44)31(46)32(47)36(50-25)49-24-11-19-20(41)12-22(43)27(35(19)51-33(24)14-1-5-16(38)6-2-14)28-26-21(42)9-18(40)10-23(26)48-34(30(28)45)15-3-7-17(39)8-4-15/h1-12,25,28-32,34,36-37,44-47H,13H2,(H5-,38,39,40,41,42,43)/p+1/t25-,28?,29-,30+,31+,32-,34-,36-/m1/s1

> <INCHI_KEY>
UCHHYHHTRCIREP-IEPQWAIVSA-O

> <FORMULA>
C36H33O15

> <MOLECULAR_WEIGHT>
705.6382

> <EXACT_MASS>
705.181945386

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
68.60200464611296

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2R,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.341899999999999

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.755509899388834

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.64039224748957

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6789504700866686

> <JCHEM_POLAR_SURFACE_AREA>
263.35999999999996

> <JCHEM_REFRACTIVITY>
184.80400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2R,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

> <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      -8.370   5.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.703   4.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.703   3.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.370   2.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.036   3.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.036   4.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.702   5.320   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.369   3.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.369   4.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.035   5.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.701   7.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.035   6.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.701   4.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.368   5.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.368   6.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.966   7.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -8.370   1.030   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -11.037   5.320   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.035   2.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.702   0.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.036  -0.070   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.036  -1.610   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.702  -2.380   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.369  -1.610   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.369  -0.070   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.035   0.700   0.000  0.00  0.00           O+1
HETATM   27  C   UNK     0      -3.035  -2.380   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.701  -1.610   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.701  -0.070   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.368   0.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.966   3.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.368   2.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.966  -0.070   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.300   0.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.300   2.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.600   0.205   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.702  -3.920   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       3.633   3.010   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -5.702   2.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.701  -4.690   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.701  -6.230   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.368  -7.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.966  -6.230   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.966  -4.690   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.368  -3.920   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.368  -2.380   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.300  -3.920   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -3.035  -7.000   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -0.368  -8.540   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.300  -7.000   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -3.035  -8.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4   39    6                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    9                                                       
CONECT    8   39    9   19                                                  
CONECT    9    7    8   10                                                  
CONECT   10    9   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15                                                            
CONECT   17    4                                                            
CONECT   18    2                                                            
CONECT   19    8                                                            
CONECT   20   21   25   39                                                  
CONECT   21   20   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   27                                                  
CONECT   25   20   26   24                                                  
CONECT   26   25   29                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   46                                                  
CONECT   29   26   28   30                                                  
CONECT   30   29   32   33                                                  
CONECT   31   32   35                                                       
CONECT   32   30   31                                                       
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   31   34   38                                                  
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   35                                                            
CONECT   39    5    8   20                                                  
CONECT   40   41   45                                                       
CONECT   41   40   42   48                                                  
CONECT   42   41   43   49                                                  
CONECT   43   42   44   50                                                  
CONECT   44   43   45   47                                                  
CONECT   45   40   44   46                                                  
CONECT   46   28   45                                                       
CONECT   47   44                                                            
CONECT   48   41   51                                                       
CONECT   49   42                                                            
CONECT   50   43                                                            
CONECT   51   48                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

View in JSmol

Synonyms

Value	Source
Afzelechin-(4a->8)-pelargonidin 3-O-b-glucopyranoside	Generator
Afzelechin-(4α->8)-pelargonidin 3-O-β-glucopyranoside	Generator

Chemical Formula

C₃₆H₃₃O₁₅

Average Mass

705.6382 Da

Monoisotopic Mass

705.18195 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2R,3S)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

Traditional Name

CAS Registry Number

753008-66-1

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(O)C=C(O)C(C4[C@H](O)[C@H](OC5=C4C(O)=CC(O)=C5)C4=CC=C(O)C=C4)=C3[O+]=C2C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C36H32O15/c37-13-25-29(44)31(46)32(47)36(50-25)49-24-11-19-20(41)12-22(43)27(35(19)51-33(24)14-1-5-16(38)6-2-14)28-26-21(42)9-18(40)10-23(26)48-34(30(28)45)15-3-7-17(39)8-4-15/h1-12,25,28-32,34,36-37,44-47H,13H2,(H5-,38,39,40,41,42,43)/p+1/t25-,28?,29-,30+,31+,32-,34-,36-/m1/s1

InChI Key

UCHHYHHTRCIREP-IEPQWAIVSA-O

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fragaria x ananassa	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Monocyclic monoterpenoid
11-noriridane monoterpenoid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.84	ALOGPS
logP	2.34	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.64	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	263.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	184.8 m³·mol⁻¹	ChemAxon
Polarizability	68.6 Å³	ChemAxon
Number of Rings	7	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

FDB001740

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside (NP0045756)

MOL for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

3D MOL for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

3D SDF for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

3D-SDF for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

PDB for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

3D PDB for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

SMILES for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

INCHI for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

Structure for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)

3D Structure for NP0045756 (Afzelechin-(4alpha->8)-pelargonidin 3-O-beta-glucopyranoside)