NP-MRD: Showing NP-Card for Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside (NP0063016)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 07:31:51 UTC

Updated at

2022-04-28 07:31:51 UTC

NP-MRD ID

NP0063016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside

Description

6-{[(2S,3R,4S,5S,6R)-6-({[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-2H-chromen-2-one belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside is found in Lonicera gracilipes var. glandulosa. Based on a literature review very few articles have been published on 6-{[(2S,3R,4S,5S,6R)-6-({[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-2H-chromen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209312D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  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
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9049   -4.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1599   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3529   -5.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -5.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787   -6.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203   -3.9425    0.0000 O   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
   -4.2868    0.0000    0.0000 O   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
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
  1 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 24 28  1  6  0  0  0
 28 29  1  0  0  0  0
 23 30  1  1  0  0  0
 17 31  1  1  0  0  0
 16 32  1  6  0  0  0
 15 33  1  1  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    9.6794    2.2356   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5456    1.7726   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3154    1.3457    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866    0.8416    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1112    0.7803    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8730    0.2785    0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8646    0.2005   -0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6670   -0.3034    0.0985 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724   -0.5345   -0.5327 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4832    0.2156    0.0896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7534    0.1113   -0.6323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6419    1.1479   -0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8864    1.3894   -0.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734    0.5402   -0.0830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7297    0.1937   -1.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6683   -0.6043   -0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1507    0.3707    0.5720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1911    1.1551    0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5829   -0.3047    1.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5523   -1.0844    2.3699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    1.2451    0.8113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1032    2.5437    0.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126   -1.2858   -0.5932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2957   -1.4012   -1.5194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1398   -2.2460   -1.0865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6207   -3.5310   -0.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1350   -2.0184   -0.3459 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1657   -2.7644   -0.8931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1564    0.6362   -1.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109    0.5883   -2.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271    1.1492   -1.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016    1.2182   -0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5943    1.6918   -1.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1216    1.4207    1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8650    0.4966    2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895   -0.0564    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -0.3346   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443    0.4237   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448    0.9903    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301    2.1437   -0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -0.3773    0.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0963   -1.4086    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4630   -0.9694   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9652    2.0977    0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5425   -0.8097    1.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7285    0.5549    2.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6456   -2.0008    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6590    1.1947    1.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4590    2.8609   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558   -1.5630    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225   -2.1914   -1.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0120   -2.0689   -2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -3.8116    0.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9892   -2.2240    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194   -2.3413   -0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    0.9200   -3.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5958    1.4807   -2.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 17  1  0
 17 18  1  6
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  9 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 14 21  1  0
 21 22  1  0
 21 17  1  0
 23 11  1  0
  6  7  1  0
  5 32  1  0
 20 47  1  0
 19 45  1  0
 19 46  1  0
 18 44  1  0
 16 42  1  0
 16 43  1  0
 14 41  1  1
 12 39  1  0
 12 40  1  0
 11 38  1  6
  9 37  1  6
 30 56  1  0
 31 57  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
 27 54  1  1
 28 55  1  0
 25 52  1  6
 26 53  1  0
 23 50  1  1
 24 51  1  0
 21 48  1  1
 22 49  1  0
M  END


  Mrv1652304282209312D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  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
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9049   -4.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1599   -4.9820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3529   -5.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -4.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -5.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5787   -6.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203   -3.9425    0.0000 O   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
   -4.2868    0.0000    0.0000 O   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
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
  1 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 24 28  1  6  0  0  0
 28 29  1  0  0  0  0
 23 30  1  1  0  0  0
 17 31  1  1  0  0  0
 16 32  1  6  0  0  0
 15 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0063016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OC3=C(O)C=C4OC(=O)C=CC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O13/c21-6-20(28)7-30-19(17(20)27)29-5-12-14(24)15(25)16(26)18(33-12)32-11-3-8-1-2-13(23)31-10(8)4-9(11)22/h1-4,12,14-19,21-22,24-28H,5-7H2/t12-,14-,15+,16-,17-,18-,19-,20+/m1/s1

> <INCHI_KEY>
JMOPDMCEDXPCRG-PRSWTWTOSA-N

> <FORMULA>
C20H24O13

> <MOLECULAR_WEIGHT>
472.399

> <EXACT_MASS>
472.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.90344106370137

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-2.3683381813333324

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.701841365877623

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.116467144197726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
104.32499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[(2S,3R,4S,5S,6R)-6-({[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.423  -7.835   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.898  -9.300   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.392  -9.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.438  -9.300   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.914  -7.835   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.059 -10.831   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.813 -11.737   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -3.958  -7.359   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   26   28                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   22                                                       
CONECT   28   24   29                                                       
CONECT   29   28                                                            
CONECT   30   23                                                            
CONECT   31   17                                                            
CONECT   32   16                                                            
CONECT   33   15                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₁₃

Average Mass

472.3990 Da

Monoisotopic Mass

472.12169 Da

IUPAC Name

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

Traditional Name

6-{[(2S,3R,4S,5S,6R)-6-({[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxychromen-2-one

CAS Registry Number

Not Available

SMILES

OC[C@]1(O)CO[C@@H](OC[C@H]2O[C@@H](OC3=C(O)C=C4OC(=O)C=CC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C20H24O13/c21-6-20(28)7-30-19(17(20)27)29-5-12-14(24)15(25)16(26)18(33-12)32-11-3-8-1-2-13(23)31-10(8)4-9(11)22/h1-4,12,14-19,21-22,24-28H,5-7H2/t12-,14-,15+,16-,17-,18-,19-,20+/m1/s1

InChI Key

JMOPDMCEDXPCRG-PRSWTWTOSA-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, 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
Lonicera gracilipes var. glandulosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin-6-o-glycoside
Coumarin o-glycoside
Phenolic glycoside
Hydroxycoumarin
7-hydroxycoumarin
O-glycosyl compound
Glycosyl compound
Disaccharide
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Oxane
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	-1.1	ALOGPS
logP	-2.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.32 m³·mol⁻¹	ChemAxon
Polarizability	43.9 Å³	ChemAxon
Number of Rings	4	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

Not Available

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

163079263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside (NP0063016)

MOL for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

3D MOL for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

3D SDF for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

3D-SDF for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

PDB for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

3D PDB for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

SMILES for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

INCHI for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

Structure for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)

3D Structure for NP0063016 (Aesculetin-6-O-beta-D-apiofuranosyl-(1->6)-O-beta-glucopyranoside)