NP-MRD: Showing NP-Card for (2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0288136)

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Record Information

Version

2.0

Created at

2022-09-09 17:43:16 UTC

Updated at

2022-09-09 17:43:16 UTC

NP-MRD ID

NP0288136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

Description

Neoisoastilbin 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. (2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one is found in Dimorphandra mollis, Iryanthera sagotiana, Litsea sericea, Petiveria alliacea, Smilax corbularia and Smilax glabra. (2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one was first documented in 2008 (PMID: 18831207). Based on a literature review a significant number of articles have been published on Neoisoastilbin (PMID: 32380350) (PMID: 29735052) (PMID: 21328178) (PMID: 35200080) (PMID: 20545194) (PMID: 35524264).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219432D          

 32 35  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
    1.4289    0.8250    0.0000 O   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  1  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
   -2.1434   -1.2375    0.0000 O   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  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.6166    0.8858    1.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -0.3059    0.8323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4249    0.0627    1.0851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5412   -0.4359    0.1044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2786   -0.1909    0.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912    0.8021   -0.1260 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4992    2.0451    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089    2.3824    1.3688 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    2.8261    0.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    4.1623    1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    4.8147    1.5545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9019    4.8872    1.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543    4.2101    1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    4.8987    1.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    2.8878    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046    2.1860    0.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7910    0.8569    0.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7150    0.4085   -0.6645 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8800   -1.0561   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089   -1.6550   -2.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9622   -3.0395   -2.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1874   -3.8122   -1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3474   -5.2049   -1.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -3.2018    0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4821   -3.9708    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1037   -1.8225    0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9028   -1.8674   -0.1210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9191   -2.6581   -0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1288   -1.8501   -1.0498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6473   -1.5966   -2.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781   -0.6760   -0.6121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3214   -1.0364   -0.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8968    0.9392    2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234    1.8155    0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4828    0.9197    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9653   -1.1753    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972    0.2213   -0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762    1.1268   -0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3818    4.5690    1.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916    5.9234    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6253    5.4014    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9952    2.3639    0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9082    0.8656   -1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -1.0982   -2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035   -3.4878   -3.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920   -5.6240   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -4.9720    1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696   -1.4063    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2573   -2.2713    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9107   -3.5828   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6622   -2.8035   -1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492   -1.5533   -2.9321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7276    0.2156   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8729   -0.3234   -1.1272 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 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
  4 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  2  1  0
  7  6  1  0
 26 19  1  0
  9 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  4 37  1  6
  6 38  1  6
 18 43  1  6
 15 42  1  0
 14 41  1  0
 12 40  1  0
 11 39  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  1
 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  6
 32 54  1  0
M  END


  Mrv1652309092219432D          

 32 35  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
    1.4289    0.8250    0.0000 O   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  1  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
   -2.1434   -1.2375    0.0000 O   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  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 19 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0288136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
ZROGCCBNZBKLEL-XEXNSLJOSA-N

> <FORMULA>
C21H22O11

> <MOLECULAR_WEIGHT>
450.396

> <EXACT_MASS>
450.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.57570928155481

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
1.0924585889999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.000676709656753

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.741338554809933

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612182875000423

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
105.47850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19                                                       
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S-cis)-Isomer OF astilbin	MeSH
3-0-alpha-1-Rhamnosyl-(2R,3R)-dihydroquercetin	MeSH
Isoastilbin	MeSH
(2R-cis)-Isomer OF astilbin	MeSH
Astilbin	MeSH

Chemical Formula

C₂₁H₂₂O₁₁

Average Mass

450.3960 Da

Monoisotopic Mass

450.11621 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19-,20-,21-/m0/s1

InChI Key

ZROGCCBNZBKLEL-XEXNSLJOSA-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
Dimorphandra mollis	LOTUS Database	35616633
Iryanthera sagotiana	LOTUS Database	35616633
Litsea sericea	LOTUS Database	35616633
Petiveria alliacea	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Smilax glabra	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
Hydroxyflavonoid
Flavanonol
Flavanone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Hexose monosaccharide
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Ether
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxide
Organic oxygen compound
Aldehyde
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008705

Chemspider ID

8290332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Astilbin

METLIN ID

Not Available

PubChem Compound

10114809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen L, Chen H, Lu Y, Han L, Wang S, Liu M, Li X, Zhao J, Lu C, Li S: Decoding active components in a formulation of multiple herbs for treatment of psoriasis based on three cell lines fishing and liquid chromatography-mass spectrometry analysis. J Pharm Biomed Anal. 2020 Jul 15;186:113331. doi: 10.1016/j.jpba.2020.113331. Epub 2020 Apr 25. [PubMed:32380350 ]
He L, Zhang Z, Liu Y, Chen D, Yuan M, Dong G, Luo P, Yan Z: Rapid discrimination of raw and sulfur-fumigated Smilax glabra based on chemical profiles by UHPLC-QTOF-MS/MS coupled with multivariate statistical analysis. Food Res Int. 2018 Jun;108:226-236. doi: 10.1016/j.foodres.2018.03.047. Epub 2018 Mar 17. [PubMed:29735052 ]
Xu YJ, Capistrano R 1st, Dhooghe L, Foubert K, Lemiere F, Maregesi S, Balde A, Apers S, Pieters L: Herbal medicines and infectious diseases: characterization by LC-SPE-NMR of some medicinal plant extracts used against malaria. Planta Med. 2011 Jul;77(11):1139-48. doi: 10.1055/s-0030-1270719. Epub 2011 Feb 15. [PubMed:21328178 ]
Botelho AS, Pinheiro WBS, Neto JRP, Pamplona SDGSR, Dos Santos KIP, Silva MND, Arruda MSP: First report of phenolic compounds isolated from Inga stipularis DC. (fabaceae) leaves. Nat Prod Res. 2022 Feb 24:1-4. doi: 10.1080/14786419.2022.2043854. [PubMed:35200080 ]
Wang C, Zhu L, Yang J, Li C, Zhang D: [Chemical constituents from Sarcandra glabra]. Zhongguo Zhong Yao Za Zhi. 2010 Mar;35(6):714-7. doi: 10.4268/cjcmm20100612. [PubMed:20545194 ]
Qiao J, Lu G, Wu G, Liu H, Wang W, Zhang T, Xie G, Qin M: Influence of different pretreatments and drying methods on the chemical compositions and bioactivities of Smilacis Glabrae Rhizoma. Chin Med. 2022 May 6;17(1):54. doi: 10.1186/s13020-022-00614-7. [PubMed:35524264 ]
Fayad S, Le Scanff M, Waffo-Teguo P, Marchal A: Understanding sweetness of dry wines: First evidence of astilbin isomers in red wines and quantitation in a one-century range of vintages. Food Chem. 2021 Aug 1;352:129293. doi: 10.1016/j.foodchem.2021.129293. Epub 2021 Feb 15. [PubMed:33657485 ]
Zhao X, Chen R, Shi Y, Zhang X, Tian C, Xia D: Antioxidant and Anti-Inflammatory Activities of Six Flavonoids from Smilax glabra Roxb. Molecules. 2020 Nov 13;25(22):5295. doi: 10.3390/molecules25225295. [PubMed:33202848 ]
Zheng D, Ruan YT, Yin ZP, Zhang QF: A Comparison of Solubility, Stability, and Bioavailability between Astilbin and Neoastilbin Isolated from Smilax glabra Rhizoma. Molecules. 2020 Oct 15;25(20):4728. doi: 10.3390/molecules25204728. [PubMed:33076319 ]
Barrientos R, Fernandez-Galleguillos C, Pastene E, Simirgiotis M, Romero-Parra J, Ahmed S, Echeverria J: Metabolomic Analysis, Fast Isolation of Phenolic Compounds, and Evaluation of Biological Activities of the Bark From Weinmannia trichosperma Cav. (Cunoniaceae). Front Pharmacol. 2020 May 27;11:780. doi: 10.3389/fphar.2020.00780. eCollection 2020. [PubMed:32536867 ]
Liang G, Nie Y, Chang Y, Zeng S, Liang C, Zheng X, Xiao D, Zhan S, Zheng Q: Protective effects of Rhizoma smilacis glabrae extracts on potassium oxonate- and monosodium urate-induced hyperuricemia and gout in mice. Phytomedicine. 2019 Jun;59:152772. doi: 10.1016/j.phymed.2018.11.032. Epub 2018 Nov 24. [PubMed:31005813 ]
Huang L, Deng J, Chen G, Zhou M, Liang J, Yan B, Shu J, Liang Y, Huang H: The anti-hyperuricemic effect of four astilbin stereoisomers in Smilax glabra on hyperuricemic mice. J Ethnopharmacol. 2019 Jun 28;238:111777. doi: 10.1016/j.jep.2019.03.004. Epub 2019 Mar 7. [PubMed:30851369 ]
Yuan M, Yan Z, Liu Y, Chen D, Yang Z, He L, Zhang Z: Chemical profiles, antioxidant activity and acute toxicity of raw and sulfur-fumigated Smilacis Glabrae Rhizoma. J Ethnopharmacol. 2019 Apr 24;234:76-84. doi: 10.1016/j.jep.2019.01.026. Epub 2019 Jan 27. [PubMed:30699362 ]
Zheng D, Zhang L, Zhang QF: Isomerization of astilbin and its application for preparation of the four stereoisomers from Rhizoma Smilacis Glabrae. J Pharm Biomed Anal. 2018 Jun 5;155:202-209. doi: 10.1016/j.jpba.2018.04.005. Epub 2018 Apr 6. [PubMed:29653345 ]
Guo W, Dong H, Wang D, Yang B, Wang X, Huang L: Separation of Seven Polyphenols from the Rhizome of Smilax glabra by Offline Two Dimension Recycling HSCCC with Extrusion Mode. Molecules. 2018 Feb 24;23(2):505. doi: 10.3390/molecules23020505. [PubMed:29495285 ]
Xu S, Shang MY, Liu GX, Xu F, Li FC, Wang X, Cai SQ: [Simultaneous determination of seven bioactive constituents in Smilacis Glabrae Rhizoma by high-performance liquid chromatography]. Zhongguo Zhong Yao Za Zhi. 2015 Feb;40(3):469-79. [PubMed:26084172 ]
Dai W, Zhao W, Gao F, Shen J, Lv D, Qi Y, Fan G: Simultaneous chemical fingerprint and quantitative analysis of Rhizoma Smilacis Glabrae by accelerated solvent extraction and high-performance liquid chromatography with tandem mass spectrometry. J Sep Sci. 2015 May;38(9):1466-75. doi: 10.1002/jssc.201401189. Epub 2015 Mar 25. [PubMed:25678068 ]
Lu CL, Zhu W, Wang M, Xu XJ, Lu CJ: Antioxidant and Anti-Inflammatory Activities of Phenolic-Enriched Extracts of Smilax glabra. Evid Based Complement Alternat Med. 2014;2014:910438. doi: 10.1155/2014/910438. Epub 2014 Nov 11. [PubMed:25477999 ]
Zheng ZG, Duan TT, He B, Tang D, Jia XB, Wang RS, Zhu JX, Xu YH, Zhu Q, Feng L: Macrophage biospecific extraction and HPLC-ESI-MSn analysis for screening immunological active components in Smilacis Glabrae Rhizoma. J Pharm Biomed Anal. 2013 Apr 15;77:44-8. doi: 10.1016/j.jpba.2013.01.003. Epub 2013 Jan 14. [PubMed:23384550 ]
Wang YH, Li L, Zhang HG, Qiao YJ: [Identification of dihydroflavonol glycoside isomers in Smilax glabra by HPLC-MS and HPLC-1H NMR]. Zhongguo Zhong Yao Za Zhi. 2008 Jun;33(11):1281-4. [PubMed:18831207 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one (NP0288136)

MOL for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0288136 ((2s,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one)