NP-MRD: Showing NP-Card for 5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0316933)

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Record Information

Version

2.0

Created at

2022-09-11 16:27:38 UTC

Updated at

2022-09-11 16:27:39 UTC

NP-MRD ID

NP0316933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Sissotrin 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. 5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Astragalus austriacus, Cicer arietinum, Cicer flexuosum, Cicer reticulatum, Cicer songaricum, Cicer tragacanthoides, Crotalaria thebaica, Dalbergia sissoo, Pueraria montana, Styphnolobium japonicum, Trifolium diffusum and Trifolium pratense. 5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one was first documented in 2015 (PMID: 26639479). Based on a literature review a significant number of articles have been published on Sissotrin (PMID: 34722760) (PMID: 33604231) (PMID: 30981705) (PMID: 30981212) (PMID: 29222826) (PMID: 28054950).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218272D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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 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
    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  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   -1.6500    0.0000 C   0  0  2  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
    5.0013   -1.2375    0.0000 C   0  0  1  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
    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
    2.8579   -2.4750    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  7 29  1  0  0  0  0
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  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -9.9325    0.3947   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9705    0.8763    0.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4174    0.0108   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793   -0.1358   -0.9349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -0.4961    0.0843 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.6351    0.2416    1.0493 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4983    1.5059    1.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9262    1.7284   -0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5397   -0.8435    0.4979 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6521   -1.9094    1.4071 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8092   -1.4202   -0.7214 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7757   -0.4862   -1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192   -1.7758   -0.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5798   -2.5796    0.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6897    0.3823   -2.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6719    0.5469   -2.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    0.9205   -3.1859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577    0.3345   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7393    0.4976   -0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3813    0.8309   -1.8538 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0293    0.0423   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1872   -0.2527    2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2126   -0.4883    1.2244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759   -0.6818    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2498    0.0279    2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3448    1.3692    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325    2.3450    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9001    1.7280   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435   -0.4944    0.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0141   -2.6739    0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315   -2.3136   -1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3868   -0.9508   -2.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8940   -2.3764   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1310   -2.1357    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    0.5485   -2.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991    1.0640   -4.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2131   -0.6350   -1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6780   -0.3701   -1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  6 31  1  0
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 32  3  1  0
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  1 33  1  0
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  8 38  1  0
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 22 48  1  0
 23 49  1  6
 24 50  1  0
 25 51  1  0
 27 52  1  0
M  END


  Mrv1652309112218272D          

 32 35  0  0  1  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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 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
    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  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
    5.0013   -1.2375    0.0000 C   0  0  1  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
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  1  2  1  0  0  0  0
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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
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 14 23  1  0  0  0  0
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 12 25  2  0  0  0  0
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  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22?/m1/s1

> <INCHI_KEY>
LFEUICHQZGNOHD-SQGFOMTPSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.25425335104197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.9546983523333339

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200145466547728

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.282050987396348

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
108.3096

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   10   29                                                  
CONECT   29   28    7   30                                                  
CONECT   30   29                                                            
CONECT   31    6   32                                                       
CONECT   32   31    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₀

Average Mass

446.4080 Da

Monoisotopic Mass

446.12130 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22?/m1/s1

InChI Key

LFEUICHQZGNOHD-SQGFOMTPSA-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
Astragalus austriacus	LOTUS Database	35616633
Cicer arietinum	LOTUS Database	35616633
Cicer flexuosum	LOTUS Database	35616633
Cicer reticulatum	LOTUS Database	35616633
Cicer songaricum	LOTUS Database	35616633
Cicer tragacanthoides	LOTUS Database	35616633
Crotalaria thebaica	LOTUS Database	35616633
Dalbergia sissoo	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Styphnolobium japonicum	LOTUS Database	35616633
Trifolium diffusum	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633

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-7-o-glycoside
4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyran
Monocyclic benzene moiety
Oxane
Monosaccharide
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.95	ChemAxon
pKa (Strongest Acidic)	7.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.31 m³·mol⁻¹	ChemAxon
Polarizability	44.25 Å³	ChemAxon
Number of Rings	4	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

C00010112

Chemspider ID

16498850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17751042

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tsamo DLF, Tamokou JD, Kengne IC, Ngnokam CDJ, Djamalladine MD, Voutquenne-Nazabadioko L, Ngnokam D: Antimicrobial and Antioxidant Secondary Metabolites from Trifolium baccarinii Chiov. (Fabaceae) and Their Mechanisms of Antibacterial Action. Biomed Res Int. 2021 Oct 22;2021:3099428. doi: 10.1155/2021/3099428. eCollection 2021. [PubMed:34722760 ]
Singh C, Anand SK, Tiwari KN, Mishra SK, Kakkar P: Phytochemical profiling and cytotoxic evaluation of Premna serratifolia L. against human liver cancer cell line. 3 Biotech. 2021 Mar;11(3):115. doi: 10.1007/s13205-021-02654-6. Epub 2021 Feb 5. [PubMed:33604231 ]
Malca-Garcia GR, Zagal D, Graham J, Nikolic D, Friesen JB, Lankin DC, Chen SN, Pauli GF: Dynamics of the isoflavone metabolome of traditional preparations of Trifolium pratense L. J Ethnopharmacol. 2019 Jun 28;238:111865. doi: 10.1016/j.jep.2019.111865. Epub 2019 Apr 11. [PubMed:30981705 ]
Lasic K, Bokulic A, Milic A, Nigovic B, Mornar A: Lipophilicity and bio-mimetic properties determination of phytoestrogens using ultra-high-performance liquid chromatography. Biomed Chromatogr. 2019 Aug;33(8):e4551. doi: 10.1002/bmc.4551. Epub 2019 May 6. [PubMed:30981212 ]
Xu X, Li X, Liang X: Application of ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites. Rapid Commun Mass Spectrom. 2018 Feb 15;32(3):262-268. doi: 10.1002/rcm.8038. [PubMed:29222826 ]
Sordon S, Poplonski J, Tronina T, Huszcza E: Microbial Glycosylation of Daidzein, Genistein and Biochanin A: Two New Glucosides of Biochanin A. Molecules. 2017 Jan 3;22(1):81. doi: 10.3390/molecules22010081. [PubMed:28054950 ]
Horo I, Kocabas F, Alankus-Caliotaskan O, Ozgokce F, Khan IA, Bedir E: Secondary Metabolites from Astragalus lycius and Their Cytotoxic Activities. Nat Prod Commun. 2016 Dec;11(12):1847-1850. [PubMed:30508348 ]
Kopecna-Zapletalova M, Krasulova K, Anzenbacher P, Hodek P, Anzenbacherova E: Interaction of isoflavonoids with human liver microsomal cytochromes P450: inhibition of CYP enzyme activities. Xenobiotica. 2017 Apr;47(4):324-331. doi: 10.1080/00498254.2016.1195028. Epub 2016 Jun 17. [PubMed:27312150 ]
Seida A, El-Hefnawy H, Abou-Hussein D, Mokhtar FA, Abdel-Naim A: Evaluation of Medicago sativa L. sprouts as antihyperlipidemic and antihyperglycemic agent. Pak J Pharm Sci. 2015 Nov;28(6):2061-74. [PubMed:26639479 ]
Yu WW, Jin C, Shuang PC, Liao H, Zhang L: [Isoflavones and flavans from Millettia nitida var. hirsutissima]. Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(12):2363-6. [PubMed:26591526 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0316933)

MOL for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0316933 (5-hydroxy-3-(4-methoxyphenyl)-7-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)