NP-MRD: Showing NP-Card for Proanthocyanidin A5' 3-galactoside (NP0049510)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:13:40 UTC

Updated at

2022-03-17 21:13:41 UTC

NP-MRD ID

NP0049510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Proanthocyanidin A5' 3-galactoside

Description

3-O-beta-D-Galactopyranosylproanthocyanidin A5' belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 3-O-beta-D-Galactopyranosylproanthocyanidin A5' is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-O-beta-D-galactopyranosylproanthocyanidin a5' has been detected, but not quantified in, cocoa and cocoa products. This could make 3-O-beta-D-galactopyranosylproanthocyanidin a5' a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209532D          

 53 60  0  0  0  0            999 V2000
    0.7907   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -1.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    0.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757   -1.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -3.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -3.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -3.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -3.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    1.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    1.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    1.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    3.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    3.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    0.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -1.0801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172    0.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    4.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579    3.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -3.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -4.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    2.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197    2.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    3.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036    3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191    2.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512    1.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172    2.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855    3.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    4.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693    4.7721    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
  1 29  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 41  1  0  0  0  0
 15 16  2  0  0  0  0
 15 42  1  0  0  0  0
 19 27  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  2  0  0  0  0
 22 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  2  0  0  0  0
 25 38  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  1  0  0  0  0
 30 31  2  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 39  1  0  0  0  0
 34 35  2  0  0  0  0
 34 40  1  0  0  0  0
 36 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 48  1  0  0  0  0
 44 45  1  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 45 50  1  0  0  0  0
 46 47  1  0  0  0  0
 46 51  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END


  Mrv0541 02241209532D          

 53 60  0  0  0  0            999 V2000
    0.7907   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -1.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2165   -0.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    0.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757   -1.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -2.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0680   -3.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -3.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393   -3.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7907   -3.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.4706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043    1.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449    1.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    1.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9171    3.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046    3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    3.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3204    0.7858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7449   -1.0801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172    0.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    4.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5579    3.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -3.9471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3544   -4.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    2.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197    2.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    3.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036    3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191    2.8017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512    1.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172    2.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7855    3.7628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    4.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7693    4.7721    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
  1 29  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 41  1  0  0  0  0
 15 16  2  0  0  0  0
 15 42  1  0  0  0  0
 19 27  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 26  1  0  0  0  0
 22 23  2  0  0  0  0
 22 29  1  0  0  0  0
 23 24  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  2  0  0  0  0
 25 38  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 30  1  0  0  0  0
 28 29  1  0  0  0  0
 28 36  1  0  0  0  0
 30 31  2  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 39  1  0  0  0  0
 34 35  2  0  0  0  0
 34 40  1  0  0  0  0
 36 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 48  1  0  0  0  0
 44 45  1  0  0  0  0
 44 49  1  0  0  0  0
 45 46  1  0  0  0  0
 45 50  1  0  0  0  0
 46 47  1  0  0  0  0
 46 51  1  0  0  0  0
 47 48  1  0  0  0  0
 47 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2C3C4=C(O)C=C(O)C=C4OC2(OC2=CC(O)=C4CC(O)C(OC4=C32)C2=CC=C(O)C(O)=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H34O17/c37-11-25-29(46)30(47)31(48)35(49-25)51-34-28-26-21(44)7-14(38)8-23(26)52-36(34,13-2-4-17(40)20(43)6-13)53-24-10-18(41)15-9-22(45)32(50-33(15)27(24)28)12-1-3-16(39)19(42)5-12/h1-8,10,22,25,28-32,34-35,37-48H,9,11H2

> <INCHI_KEY>
JUIIUJBWZYKSEP-UHFFFAOYSA-N

> <FORMULA>
C36H34O17

> <MOLECULAR_WEIGHT>
738.645

> <EXACT_MASS>
738.179599662

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
71.05232007329279

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,13-bis(3,4-dihydroxyphenyl)-21-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19-tetrol

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.819696451

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.104094746178864

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.662652725538374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.947737823953653

> <JCHEM_POLAR_SURFACE_AREA>
288.90999999999997

> <JCHEM_REFRACTIVITY>
176.6096000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,13-bis(3,4-dihydroxyphenyl)-21-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19-tetrol

> <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       1.476  -0.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.476  -1.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.808  -2.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.137  -1.975   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.137  -0.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.808   0.332   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.141  -2.745   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.141  -4.288   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.476  -5.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.808  -4.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.193  -5.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.528  -4.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.860  -5.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.860  -6.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.528  -7.368   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.193  -6.598   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.476  -6.598   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.472  -2.745   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.808   1.872   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.565   1.983   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.025   1.983   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.257   0.651   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.025  -0.681   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.565  -0.681   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.332   0.651   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.257   3.315   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.712   3.315   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.942   1.983   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.712   0.651   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.942   4.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.712   5.984   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.942   7.317   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.598   7.317   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.368   5.984   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.598   4.650   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.598   1.467   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -3.257  -2.016   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -7.872   0.651   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.368   8.654   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.908   5.984   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.195  -7.368   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -2.528  -8.908   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.807   3.751   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.295   3.353   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.383   4.444   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.981   5.933   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.487   6.328   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       3.396   5.230   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       5.696   1.872   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       7.872   4.049   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       7.066   7.024   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       4.084   7.814   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.169   8.908   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   19                                                  
CONECT    7    2    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   17                                                  
CONECT   10    3    9                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   11   15                                                       
CONECT   17    9                                                            
CONECT   18    4                                                            
CONECT   19    6   27                                                       
CONECT   20   21   25                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   37                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24   38                                                  
CONECT   26   21   27                                                       
CONECT   27   19   26   28   30                                             
CONECT   28   27   29   36                                                  
CONECT   29    1   22   28                                                  
CONECT   30   27   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35   40                                                  
CONECT   35   30   34                                                       
CONECT   36   28   43                                                       
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   33                                                            
CONECT   40   34                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   36   44   48                                                  
CONECT   44   43   45   49                                                  
CONECT   45   44   46   50                                                  
CONECT   46   45   47   51                                                  
CONECT   47   46   48   52                                                  
CONECT   48   43   47                                                       
CONECT   49   44                                                            
CONECT   50   45                                                            
CONECT   51   46                                                            
CONECT   52   47   53                                                       
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  120    0
END

View in JSmol

Synonyms

Value	Source
3-O-b-D-Galactopyranosylproanthocyanidin a5'	Generator
3-O-Β-D-galactopyranosylproanthocyanidin a5'	Generator

Chemical Formula

C₃₆H₃₄O₁₇

Average Mass

738.6450 Da

Monoisotopic Mass

738.17960 Da

IUPAC Name

5,13-bis(3,4-dihydroxyphenyl)-21-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19-tetrol

Traditional Name

5,13-bis(3,4-dihydroxyphenyl)-21-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19-tetrol

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2C3C4=C(O)C=C(O)C=C4OC2(OC2=CC(O)=C4CC(O)C(OC4=C32)C2=CC=C(O)C(O)=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H34O17/c37-11-25-29(46)30(47)31(48)35(49-25)51-34-28-26-21(44)7-14(38)8-23(26)52-36(34,13-2-4-17(40)20(43)6-13)53-24-10-18(41)15-9-22(45)32(50-33(15)27(24)28)12-1-3-16(39)19(42)5-12/h1-8,10,22,25,28-32,34-35,37-48H,9,11H2

InChI Key

JUIIUJBWZYKSEP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Theobroma cacao	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Not Available

Substituents

Not Available

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	1.62	ALOGPS
logP	1.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	288.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	176.61 m³·mol⁻¹	ChemAxon
Polarizability	71.05 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039862

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019520

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

14841172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Proanthocyanidin A5' 3-galactoside (NP0049510)

MOL for NP0049510 (Proanthocyanidin A5' 3-galactoside)

3D MOL for NP0049510 (Proanthocyanidin A5' 3-galactoside)

3D SDF for NP0049510 (Proanthocyanidin A5' 3-galactoside)

3D-SDF for NP0049510 (Proanthocyanidin A5' 3-galactoside)

PDB for NP0049510 (Proanthocyanidin A5' 3-galactoside)

3D PDB for NP0049510 (Proanthocyanidin A5' 3-galactoside)

SMILES for NP0049510 (Proanthocyanidin A5' 3-galactoside)

INCHI for NP0049510 (Proanthocyanidin A5' 3-galactoside)

Structure for NP0049510 (Proanthocyanidin A5' 3-galactoside)

3D Structure for NP0049510 (Proanthocyanidin A5' 3-galactoside)