NP-MRD: Showing NP-Card for Aesculin (NP0333007)

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Record Information

Version

2.0

Created at

2024-05-03 07:32:10 UTC

Updated at

2026-02-17 02:00:39 UTC

NP-MRD ID

NP0333007

Natural Product DOI

https://doi.org/10.57994/2296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aesculin

Description

Aesculin, also known as esculoside or venoplant, 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. Aesculin 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. Aesculin was first documented in 2019 (PMID: 30348388). Based on a literature review a significant number of articles have been published on Aesculin (PMID: 34315523) (PMID: 34059101) (PMID: 34596507) (PMID: 34542393) (PMID: 34541621) (PMID: 34482222).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043870
     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.9765   -0.0689   -2.1967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.1141   -1.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8218   -0.3495   -2.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4063   -2.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302   -0.2223   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.2683   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.0869    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3561   -0.1239    1.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.3451    0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5245    0.8625    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    0.5103   -0.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4001    1.6941   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.2495   -1.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073    0.0092    0.7816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5227   -0.9707    0.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483   -0.5489    1.9140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3948    0.4927    2.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3215    1.2636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2056   -2.2587    0.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    0.1470    1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    0.3273    3.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586    0.1937    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344    0.0090   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692    0.0547   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -0.4851   -3.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -0.5854   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -0.4528   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7663   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -0.3001   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3690    1.3883   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6796    2.4818   -0.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1430    2.8124   -2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3012    0.8494    1.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094   -0.6323    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.2237    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    1.0807    3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -1.8803    2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -2.4256   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.2966    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    0.3777    1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 18  9  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  1
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END


  Mrv1652306222119262D          

 24 26  0  0  1  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  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
    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 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
    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  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
  6 11  1  0  0  0  0
  1 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  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
 13 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 16 21  1  1  0  0  0
 15 22  1  6  0  0  0
 14 23  1  1  0  0  0
  8 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1

> <INCHI_KEY>
XHCADAYNFIFUHF-TVKJYDDYSA-N

> <FORMULA>
C15H16O9

> <MOLECULAR_WEIGHT>
340.284

> <EXACT_MASS>
340.079432095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.59764352964134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-1.0918391213333336

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200222650441898

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.116544190796061

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549120067

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
77.6548

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-esculin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043870
     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.9765   -0.0689   -2.1967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.1141   -1.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8218   -0.3495   -2.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4063   -2.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302   -0.2223   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.2683   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.0869    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3561   -0.1239    1.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.3451    0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5245    0.8625    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    0.5103   -0.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4001    1.6941   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.2495   -1.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073    0.0092    0.7816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5227   -0.9707    0.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483   -0.5489    1.9140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3948    0.4927    2.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3215    1.2636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2056   -2.2587    0.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    0.1470    1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    0.3273    3.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586    0.1937    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344    0.0090   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692    0.0547   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -0.4851   -3.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -0.5854   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -0.4528   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7663   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -0.3001   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3690    1.3883   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6796    2.4818   -0.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1430    2.8124   -2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3012    0.8494    1.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094   -0.6323    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.2237    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    1.0807    3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -1.8803    2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -2.4256   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.2966    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    0.3777    1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 18  9  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  1
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6    1                                                  
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    NP0043870
HETATM    1  O1  UNL     1       6.976  -0.069  -2.197  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.767  -0.114  -1.793  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.822  -0.349  -2.770  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.498  -0.406  -2.378  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.230  -0.222  -1.037  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.913  -0.268  -0.584  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.627  -0.087   0.744  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.356  -0.124   1.222  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.841  -0.345   0.545  1.00  0.00           C  
HETATM   10  O3  UNL     1      -1.524   0.862   0.283  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.757   0.510  -0.317  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.400   1.694  -0.969  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.617   2.249  -1.964  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.707   0.009   0.782  1.00  0.00           C  
HETATM   15  O5  UNL     1      -4.523  -0.971   0.270  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.848  -0.549   1.914  1.00  0.00           C  
HETATM   17  O6  UNL     1      -2.395   0.493   2.686  1.00  0.00           O  
HETATM   18  C12 UNL     1      -1.719  -1.322   1.264  1.00  0.00           C  
HETATM   19  O7  UNL     1      -2.206  -2.259   0.358  1.00  0.00           O  
HETATM   20  C13 UNL     1       2.660   0.147   1.663  1.00  0.00           C  
HETATM   21  O8  UNL     1       2.326   0.327   3.010  1.00  0.00           O  
HETATM   22  C14 UNL     1       3.959   0.194   1.227  1.00  0.00           C  
HETATM   23  C15 UNL     1       4.234   0.009  -0.118  1.00  0.00           C  
HETATM   24  O9  UNL     1       5.469   0.055  -0.532  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.088  -0.485  -3.797  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.687  -0.585  -3.075  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.143  -0.453  -1.335  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.611  -0.766  -0.469  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.586  -0.300  -1.045  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.369   1.388  -1.415  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.680   2.482  -0.220  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.143   2.812  -2.584  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.301   0.849   1.186  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.409  -0.632   0.042  1.00  0.00           H  
HETATM   35  H11 UNL     1      -3.471  -1.224   2.499  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.102   1.081   3.011  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.206  -1.880   2.076  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.458  -2.426  -0.282  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.375   0.297   3.332  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.743   0.378   1.963  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   23
CONECT    6    7   27
CONECT    7    8   20   20
CONECT    8    9
CONECT    9   10   18   28
CONECT   10   11
CONECT   11   12   14   29
CONECT   12   13   30   31
CONECT   13   32
CONECT   14   15   16   33
CONECT   15   34
CONECT   16   17   18   35
CONECT   17   36
CONECT   18   19   37
CONECT   19   38
CONECT   20   21   22
CONECT   21   39
CONECT   22   23   23   40
CONECT   23   24
END

NP0043870
     RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
    6.9765   -0.0689   -2.1967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -0.1141   -1.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8218   -0.3495   -2.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4063   -2.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2302   -0.2223   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.2683   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.0869    0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3561   -0.1239    1.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -0.3451    0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5245    0.8625    0.2829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    0.5103   -0.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4001    1.6941   -0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169    2.2495   -1.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7073    0.0092    0.7816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5227   -0.9707    0.2699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8483   -0.5489    1.9140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3948    0.4927    2.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192   -1.3215    1.2636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2056   -2.2587    0.3584 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596    0.1470    1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3256    0.3273    3.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586    0.1937    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344    0.0090   -0.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4692    0.0547   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885   -0.4851   -3.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -0.5854   -3.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -0.4528   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -0.7663   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863   -0.3001   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3690    1.3883   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6796    2.4818   -0.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1430    2.8124   -2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3012    0.8494    1.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4094   -0.6323    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -1.2237    2.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024    1.0807    3.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -1.8803    2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -2.4256   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.2966    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7432    0.3777    1.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 18  9  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  9 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  1
 15 34  1  0
 16 35  1  1
 17 36  1  0
 18 37  1  1
 19 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol

Synonyms

Value	Source
6,7-Dihydroxycoumarin 6-glucoside	ChEBI
6,7-Dihydroxycoumarin-6-O-glucoside	ChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one	ChEBI
6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin	ChEBI
7-Hydroxy-6-glucosyloxy-2H-chromene	ChEBI
Esculetin 6-beta-D-glucoside	ChEBI
Esculetin 6-O-glucoside	ChEBI
Esculoside	ChEBI
6-(b-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one	Generator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one	Generator
6-(b-D-Glucopyranosyloxy)-7-hydroxy-cumarin	Generator
6-(Β-D-glucopyranosyloxy)-7-hydroxy-cumarin	Generator
Esculetin 6-b-D-glucoside	Generator
Esculetin 6-β-D-glucoside	Generator
Venoplant	HMDB
(-)-Esculin	HMDB
6-(beta-D-Glucopyranosyloxy)-7-hydroxycoumarin	HMDB
6-(Β-D-glucopyranosyloxy)-7-hydroxycoumarin	HMDB
Esculin	HMDB
Esculine	HMDB
Aesculin	ChEBI, MeSH

Chemical Formula

C₁₅H₁₆O₉

Average Mass

340.2840 Da

Monoisotopic Mass

340.07943 Da

IUPAC Name

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

Traditional Name

(-)-esculin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1

InChI Key

XHCADAYNFIFUHF-TVKJYDDYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
MLEV NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.0, Methanol-d4, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802, C2D6OS, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-03	View Spectrum

Species

Species of Origin

Not Available

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 o-glycoside
Coumarin-6-o-glycoside
Phenolic glycoside
7-hydroxycoumarin
Hydroxycoumarin
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:4853 )
hydroxycoumarin (CHEBI:4853 )
coumarins (C09264 )

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	-0.53	ALOGPS
logP	-1.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.65 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030820

DrugBank ID

DB13155

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Aesculin

METLIN ID

Not Available

PubChem Compound

5281417

PDB ID

Not Available

ChEBI ID

4853

Good Scents ID

rw1242871

References

General References

Lather A, Sharma S, Khatkar A: Aesculin based glucosamine-6-phosphate synthase inhibitors as novel preservatives for food and pharmaceutical products: in-silico studies, antioxidant, antimicrobial and preservative efficacy evaluation. BMC Chem. 2021 Jul 27;15(1):45. doi: 10.1186/s13065-021-00769-8. [PubMed:34315523 ]
Yu Y, Chen J, Zhang X, Wang Y, Wang S, Zhao L, Wang Y: Identification of anti-inflammatory compounds from Zhongjing formulae by knowledge mining and high-content screening in a zebrafish model of inflammatory bowel diseases. Chin Med. 2021 May 31;16(1):42. doi: 10.1186/s13020-021-00452-z. [PubMed:34059101 ]
Panosyan H, Margaryan A, Birkeland NK: Anoxybacillus karvacharensis sp. nov., a novel thermophilic bacterium isolated from the Karvachar geothermal spring in Nagorno-Karabakh. Int J Syst Evol Microbiol. 2021 Oct;71(10):005035. doi: 10.1099/ijsem.0.005035. [PubMed:34596507 ]
Choi JY, Choi SH, Park JE, Kim JS, Lee J, Lee MK, Lee JS, Lee JH, Jung H, Hur TY, Kim HB, Lee JH, Kim JK, Kang SW, Park SH: Phocaeicola faecicola sp. nov., isolated from porcine faeces. Int J Syst Evol Microbiol. 2021 Sep;71(9). doi: 10.1099/ijsem.0.005008. [PubMed:34542393 ]
Menes RJ, Machin EV, Roldan DM, Kyrpides N, Woyke T, Whitman WB, Busse HJ: Frigoriflavimonas asaccharolytica gen. nov., sp. nov., a novel psychrophilic esterase and protease producing bacterium isolated from Antarctica. Antonie Van Leeuwenhoek. 2021 Dec;114(12):1991-2002. doi: 10.1007/s10482-021-01656-x. Epub 2021 Sep 20. [PubMed:34541621 ]
Xu XN, Jiang Y, Yan LY, Yin SY, Wang YH, Wang SB, Fang LH, Du GH: Aesculin suppresses the NLRP3 inflammasome-mediated pyroptosis via the Akt/GSK3beta/NF-kappaB pathway to mitigate myocardial ischemia/reperfusion injury. Phytomedicine. 2021 Nov;92:153687. doi: 10.1016/j.phymed.2021.153687. Epub 2021 Aug 23. [PubMed:34482222 ]
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DOI: 10.1016/j.talanta.2018.09.036
PMID: 30348388

Showing NP-Card for Aesculin (NP0333007)

MOL for NP0333007 (Aesculin)

3D MOL for NP0333007 (Aesculin)

3D SDF for NP0333007 (Aesculin)

3D-SDF for NP0333007 (Aesculin)

PDB for NP0333007 (Aesculin)

3D PDB for NP0333007 (Aesculin)

SMILES for NP0333007 (Aesculin)

INCHI for NP0333007 (Aesculin)

Structure for NP0333007 (Aesculin)

3D Structure for NP0333007 (Aesculin)