NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol (NP0164497)

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Record Information

Version

2.0

Created at

2022-09-02 23:23:08 UTC

Updated at

2022-09-02 23:23:09 UTC

NP-MRD ID

NP0164497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol

Description

Afzelechin 3-o-alpha-l-rhamnopyranoside 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. Thus, afzelechin 3-O-alpha-L-rhamnopyranoside is considered to be a flavonoid. (2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol is found in Artocarpus dadah, Artocarpus tonkinensis, Cassipourea gummiflua and Cassipourea malosana. (2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol was first documented in 2018 (PMID: 30297618). Based on a literature review a small amount of articles have been published on Afzelechin 3-o-alpha-l-rhamnopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201232D          

 30 33  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    4.6391    1.4252    1.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8710    0.6892    0.3484 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5753    0.5556    0.7171 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977   -0.2963   -0.0131 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6449    0.4104   -0.3816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -0.0962    0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0767    0.9516    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8137    2.0148    0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856    3.2349    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4954    3.5426    2.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746    4.2122    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1642    3.9378   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605    4.8898   -1.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801    2.7047   -1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913    1.7090   -0.8802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.4786   -1.4738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4185   -0.5637   -0.8764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2914   -1.6149   -0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3979   -1.2812    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134   -2.2836    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9278   -3.6028    0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7443   -4.5930    1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072   -3.9197   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782   -2.9301   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -0.9258   -1.1998 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7945   -2.2057   -1.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8445   -1.1025   -1.2456 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2497   -2.3828   -1.6259 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -0.7191    0.1069 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8156   -0.7040    0.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9639    2.2385    1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578    0.7709    2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5217    1.9493    0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9024    1.2834   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4457   -1.1063    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199   -0.9647    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1936    1.4667    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    0.5475    1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9907    2.8927    2.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131    5.1926    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807    5.4755   -2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517    2.4543   -2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7436   -1.0153   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208   -0.2387    0.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0893   -1.9808    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5479   -4.9495    2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -4.9524   -0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -3.2335   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700   -0.3649   -2.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3420   -2.8946   -0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3175   -0.3975   -1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3009   -2.3965   -2.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0020   -1.3766    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941    0.0644    0.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  4 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29  2  1  0
 17  6  1  0
 24 18  1  0
 15  8  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  6
  4 35  1  1
  6 36  1  1
  7 37  1  0
  7 38  1  0
 10 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  6
 19 44  1  0
 20 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  6
 26 50  1  0
 27 51  1  6
 28 52  1  0
 29 53  1  1
 30 54  1  0
M  END


  Mrv1652309032201232D          

 30 33  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0164497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O9/c1-9-17(25)18(26)19(27)21(28-9)30-16-8-13-14(24)6-12(23)7-15(13)29-20(16)10-2-4-11(22)5-3-10/h2-7,9,16-27H,8H2,1H3/t9-,16-,17-,18+,19+,20+,21-/m0/s1

> <INCHI_KEY>
SQJLTDFIOMWZDE-QUYVSAIISA-N

> <FORMULA>
C21H24O9

> <MOLECULAR_WEIGHT>
420.414

> <EXACT_MASS>
420.142032353

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.2314857116611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
1.3747466579999994

> <ALOGPS_LOGS>
-2.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.730436819668396

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.148500100107714

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121825923590567

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
102.8884

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    6   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25    4   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    2   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Afzelechin 3-O-a-L-rhamnopyranoside	Generator
Afzelechin 3-O-α-L-rhamnopyranoside	Generator

Chemical Formula

C₂₁H₂₄O₉

Average Mass

420.4140 Da

Monoisotopic Mass

420.14203 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

(2S,3R,4R,5R,6S)-2-{[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@H]2CC3=C(O)C=C(O)C=C3O[C@@H]2C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H24O9/c1-9-17(25)18(26)19(27)21(28-9)30-16-8-13-14(24)6-12(23)7-15(13)29-20(16)10-2-4-11(22)5-3-10/h2-7,9,16-27H,8H2,1H3/t9-,16-,17-,18+,19+,20+,21-/m0/s1

InChI Key

SQJLTDFIOMWZDE-QUYVSAIISA-N

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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artocarpus dadah	LOTUS Database	35616633
Artocarpus tonkinensis	LOTUS Database	35616633
Cassipourea gummiflua	LOTUS Database	35616633
Cassipourea malosana	LOTUS Database	35616633

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
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
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	0.76	ALOGPS
logP	1.37	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.89 m³·mol⁻¹	ChemAxon
Polarizability	42.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008834

Chemspider ID

24716806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ahmed QU, Alhassan AM, Khatib A, Shah SAA, Hasan MM, Sarian MN: Antiradical and Xanthine Oxidase Inhibitory Activity Evaluations of Averrhoa bilimbi L. Leaves and Tentative Identification of Bioactive Constituents through LC-QTOF-MS/MS and Molecular Docking Approach. Antioxidants (Basel). 2018 Oct 8;7(10):137. doi: 10.3390/antiox7100137. [PubMed:30297618 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol (NP0164497)

MOL for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

3D MOL for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

3D SDF for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

3D-SDF for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

PDB for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

3D PDB for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

SMILES for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

INCHI for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

Structure for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)

3D Structure for NP0164497 ((2s,3r,4r,5r,6s)-2-{[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-6-methyloxane-3,4,5-triol)