NP-MRD: Showing NP-Card for (+)-Asphodelin A 4'-O-beta-D-glucoside (NP0076196)

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Record Information

Version

2.0

Created at

2022-04-28 21:20:55 UTC

Updated at

2022-04-28 21:20:55 UTC

NP-MRD ID

NP0076196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Asphodelin A 4'-O-beta-D-glucoside

Description

Asphodelin A-4'-O-beta-glucoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Asphodelin A-4'-O-beta-glucoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-Asphodelin A 4'-O-beta-D-glucoside is found in Asphodelus aestivus and Asphodelus microcarpus . (+)-Asphodelin A 4'-O-beta-D-glucoside was first documented in 2007 (PMID: 17253862). Based on a literature review very few articles have been published on asphodelin A-4'-O-beta-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223202D          

 32 35  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 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 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
    1.4289   -1.6500    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
    2.8579   -1.6500    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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
    5.0013   -2.8875    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 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
  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  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
 14 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    3.2506   -2.8082   -1.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205   -1.8061   -0.8905 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2111   -1.7814   -1.1103 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9544   -0.7494   -0.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3267   -0.7513   -0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0887    0.3142   -0.5790 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4466    0.2948   -0.8329 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5507    1.4135    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1908    1.4085    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3987    0.3360   -0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357    0.3145    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4016    1.3516    0.7835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -0.7851   -0.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -0.7817   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9255   -0.2641   -0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327   -0.2739   -0.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -0.7979    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -0.8427    0.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.3944    0.1598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9522    0.6293    0.9214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204    1.3587    0.0236 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0812    2.6830    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8631    3.4416   -0.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9282    0.5488   -0.3248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2416    0.7317   -1.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8003   -0.9044    0.0494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2821   -1.1077    1.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4023   -1.4295   -0.0889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2577   -1.9660   -1.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129   -1.3128    1.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3526   -1.3097    1.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -1.8244    2.0681 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7540   -1.6106   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0807    1.0357   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1890    2.2278    0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325    2.2466    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661    2.1912    1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.1505   -1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264    0.1368   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0962    0.0608   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0974    1.5648   -0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1517    3.2707    0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6035    2.5622    1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8346    4.3800    0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    0.9548    0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9888   -0.0649   -2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4932   -1.4787   -0.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7254   -1.8715    1.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3050   -2.3076    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221   -2.4370   -1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -1.7368    2.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9202   -2.2105    2.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 30  2  0
 30 31  1  0
 31 32  1  0
 31 14  2  0
 14 15  1  0
 15 16  2  0
 14 13  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
 19 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 21  1  0
 16 17  1  0
  2 13  1  0
  4 10  1  0
 23 44  1  0
 22 42  1  0
 22 43  1  0
 21 41  1  6
 19 40  1  6
 30 51  1  0
 32 52  1  0
 15 38  1  0
 16 39  1  0
 12 37  1  0
  9 36  1  0
  8 35  1  0
  7 34  1  0
  5 33  1  0
 28 49  1  1
 29 50  1  0
 26 47  1  6
 27 48  1  0
 24 45  1  1
 25 46  1  0
M  END


  Mrv1652304282223202D          

 32 35  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 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 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
    1.4289   -1.6500    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
    2.8579   -1.6500    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   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
    5.0013   -2.8875    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 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
  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  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  1  0  0  0
 26 27  1  0  0  0  0
 23 28  1  6  0  0  0
 22 29  1  1  0  0  0
 21 30  1  6  0  0  0
 14 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C(C=C2)C2=C(O)C3=CC=C(O)C=C3OC2=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-14-17(26)18(27)19(28)21(32-14)30-9-2-4-10(12(24)6-9)15-16(25)11-3-1-8(23)5-13(11)31-20(15)29/h1-6,14,17-19,21-28H,7H2/t14-,17-,18+,19-,21-/m1/s1

> <INCHI_KEY>
OEZWCAHAQBRTTP-FKRBRYKNSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.782212575686636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
-0.48086354666666625

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.956893841421521

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.008770798626267

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225725

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
105.98010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dihydroxy-3-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-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  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3                                                       
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   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   18                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   22                                                            
CONECT   30   21                                                            
CONECT   31   14                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-(2'-Hydroxy-p-O-beta-D-glucopyranosyloxyphenyl)-4,7-dihydroxy-2H-1-benzopyran-2-one	ChEBI
3-(2'-Hydroxy-p-O-b-D-glucopyranosyloxyphenyl)-4,7-dihydroxy-2H-1-benzopyran-2-one	Generator
3-(2'-Hydroxy-p-O-β-D-glucopyranosyloxyphenyl)-4,7-dihydroxy-2H-1-benzopyran-2-one	Generator
Asphodelin a-4'-O-b-glucoside	Generator
Asphodelin a-4'-O-β-glucoside	Generator
Asphodelin a 4'-O-beta-D-glucoside	MeSH

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

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

Traditional Name

4,7-dihydroxy-3-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-2-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C(C=C2)C2=C(O)C3=CC=C(O)C=C3OC2=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-14-17(26)18(27)19(28)21(32-14)30-9-2-4-10(12(24)6-9)15-16(25)11-3-1-8(23)5-13(11)31-20(15)29/h1-6,14,17-19,21-28H,7H2/t14-,17-,18+,19-,21-/m1/s1

InChI Key

OEZWCAHAQBRTTP-FKRBRYKNSA-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
Asphodelus aestivus	LOTUS Database	35616633
Asphodelus microcarpus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-4p-o-glycoside
Hydroxyisoflavonoid
Isoflav-3-enone skeleton
Phenolic glycoside
4-hydroxycoumarin
7-hydroxycoumarin
Hexose monosaccharide
Hydroxycoumarin
Coumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Pyran
Vinylogous acid
Heteroaromatic compound
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:65454 )
polyphenol (CHEBI:65454 )
hydroxycoumarin (CHEBI:65454 )

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	0.52	ALOGPS
logP	-0.48	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.98 m³·mol⁻¹	ChemAxon
Polarizability	42.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

23278395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54679753

PDB ID

Not Available

ChEBI ID

65454

Good Scents ID

Not Available

References

General References

El-Seedi HR: Antimicrobial arylcoumarins from Asphodelus microcarpus. J Nat Prod. 2007 Jan;70(1):118-20. doi: 10.1021/np060444u. [PubMed:17253862 ]

Showing NP-Card for (+)-Asphodelin A 4'-O-beta-D-glucoside (NP0076196)

MOL for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

3D MOL for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

3D SDF for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

3D-SDF for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

PDB for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

3D PDB for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

SMILES for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

INCHI for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

Structure for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)

3D Structure for NP0076196 ((+)-Asphodelin A 4'-O-beta-D-glucoside)