NP-MRD: Showing NP-Card for 7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione (NP0268154)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 13:11:07 UTC

Updated at

2022-09-08 13:11:07 UTC

NP-MRD ID

NP0268154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione

Description

Edgeworoside C 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. 7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione is found in Edgeworthia chrysantha. 7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione was first documented in 2004 (PMID: 15330108). Based on a literature review a small amount of articles have been published on Edgeworoside C (PMID: 16269220) (PMID: 32842606) (PMID: 24531219).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215112D          

 34 38  0  0  1  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    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
    0.0000   -1.6500    0.0000 O   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
    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
    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 O   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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    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
  5  6  1  0  0  0  0
  6  7  2  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 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
 18 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
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  2  0  0  0  0
 22 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    5.0852   -0.2157   -0.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149   -0.0482    0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9020   -0.4456    0.0181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    0.4531   -0.4005 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7080   -0.0804   -0.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -0.3496   -1.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0596   -0.0946   -2.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952   -0.3958   -3.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2970   -0.9339   -2.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3074   -1.2232   -3.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5027   -1.7612   -3.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6040   -1.9814   -2.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7048   -2.4783   -1.7163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386   -1.7006   -1.2799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780   -1.1827   -1.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4851   -0.8994   -0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -1.1552    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3105   -2.3615    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7771   -3.3728    0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -2.6101    2.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0048   -1.6179    3.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622   -0.4072    2.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931    0.5638    3.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2465    1.7810    3.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    1.9244    1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3725    3.0470    1.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381    0.9731    1.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -0.1905    1.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    1.7805    0.3027 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0253    2.5853   -0.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3799    2.3443    0.2094 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8351    2.5118   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806    1.3396    0.9100 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9477    1.3798    2.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927    0.4483   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1303   -0.0521   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0219   -1.2529   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5119   -0.7443    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567    0.6618   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686    0.3309   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -0.1954   -4.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795   -1.0338   -4.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3256   -2.0078   -4.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6233   -3.2731   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1954   -3.5599    3.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501   -1.7753    4.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288    0.3880    4.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567    2.5371    3.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7643    1.6255    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    3.4538    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4489    3.3103    0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    3.3758   -1.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3096    1.7194    0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.8656    2.8205 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 28  2  0
 28 27  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  2  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
  4 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33  2  1  0
 16  6  1  0
 18 17  1  0
 15  9  1  0
 22 28  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  4 39  1  6
  7 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 24 48  1  0
 23 47  1  0
 21 46  1  0
 20 45  1  0
 19 44  1  0
 29 49  1  1
 30 50  1  0
 31 51  1  1
 32 52  1  0
 33 53  1  1
 34 54  1  0
M  END


  Mrv1652309082215112D          

 34 38  0  0  1  0            999 V2000
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    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
    0.0000   -1.6500    0.0000 O   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
    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
    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 O   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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    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
  5  6  1  0  0  0  0
  6  7  2  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
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 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
 18 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
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 28  2  0  0  0  0
 22 28  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0268154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC=C3C=CC(=O)OC3=C2C2=C3OC(=O)C=CC3=CC=C2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H20O10/c1-10-19(28)20(29)21(30)24(31-10)32-14-7-3-12-5-9-16(27)34-23(12)18(14)17-13(25)6-2-11-4-8-15(26)33-22(11)17/h2-10,19-21,24-25,28-30H,1H3/t10-,19-,20+,21+,24-/m0/s1

> <INCHI_KEY>
DQEAAVKYRCHQOQ-NYPUNPOJSA-N

> <FORMULA>
C24H20O10

> <MOLECULAR_WEIGHT>
468.414

> <EXACT_MASS>
468.105646844

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.893290258662546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-7'-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2H,2'H-[8,8'-bichromene]-2,2'-dione

> <JCHEM_LOGP>
1.4124100066666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.213596249904306

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.303314874806004

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612200363169193

> <JCHEM_POLAR_SURFACE_AREA>
151.98

> <JCHEM_REFRACTIVITY>
116.73790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-7'-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   17   22                                                  
CONECT   29    4   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀O₁₀

Average Mass

468.4140 Da

Monoisotopic Mass

468.10565 Da

IUPAC Name

7-hydroxy-7'-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2H,2'H-[8,8'-bichromene]-2,2'-dione

Traditional Name

7-hydroxy-7'-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=CC=C3C=CC(=O)OC3=C2C2=C3OC(=O)C=CC3=CC=C2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C24H20O10/c1-10-19(28)20(29)21(30)24(31-10)32-14-7-3-12-5-9-16(27)34-23(12)18(14)17-13(25)6-2-11-4-8-15(26)33-22(11)17/h2-10,19-21,24-25,28-30H,1H3/t10-,19-,20+,21+,24-/m0/s1

InChI Key

DQEAAVKYRCHQOQ-NYPUNPOJSA-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
Edgeworthia chrysantha	LOTUS Database	35616633

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-7-o-glycoside
Coumarin o-glycoside
Phenolic glycoside
7-hydroxycoumarin
Hexose monosaccharide
Hydroxycoumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Monosaccharide
Oxane
Pyran
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	1.41	ChemAxon
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.74 m³·mol⁻¹	ChemAxon
Polarizability	43.89 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00019853

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

101835682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang S, Cheng Y: Separation and determination of the effective components in the alabastrum of Edgeworthia chrysantha Lindl. by micellar electrokinetic capillary chromatography. J Pharm Biomed Anal. 2006 Mar 18;40(5):1137-42. doi: 10.1016/j.jpba.2005.09.001. Epub 2005 Nov 2. [PubMed:16269220 ]
Vivek-Ananth RP, Rana A, Rajan N, Biswal HS, Samal A: In Silico Identification of Potential Natural Product Inhibitors of Human Proteases Key to SARS-CoV-2 Infection. Molecules. 2020 Aug 22;25(17):3822. doi: 10.3390/molecules25173822. [PubMed:32842606 ]
Li XN, Tong SQ, Cheng DP, Li QY, Yan JZ: Coumarins from Edgeworthia chrysantha. Molecules. 2014 Feb 13;19(2):2042-8. doi: 10.3390/molecules19022042. [PubMed:24531219 ]
Yan J, Tong S, Chu J, Sheng L, Chen G: Preparative isolation and purification of syringin and edgeworoside C from Edgeworthia chrysantha Lindl by high-speed counter-current chromatography. J Chromatogr A. 2004 Jul 23;1043(2):329-32. doi: 10.1016/j.chroma.2004.05.087. [PubMed:15330108 ]
LOTUS database [Link]

Showing NP-Card for 7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione (NP0268154)

MOL for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

3D MOL for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

3D SDF for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

3D-SDF for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

PDB for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

3D PDB for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

SMILES for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

INCHI for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

Structure for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)

3D Structure for NP0268154 (7-hydroxy-7'-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-[8,8'-bichromene]-2,2'-dione)