NP-MRD: Showing NP-Card for 5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside (NP0057202)

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Record Information

Version

2.0

Created at

2022-04-28 02:42:24 UTC

Updated at

2022-04-28 02:42:24 UTC

NP-MRD ID

NP0057202

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside

Description

MEGxp0_000947 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. Thus, megxp0_000947 is considered to be a flavonoid. 5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside is found in Coutarea hexandra , Exostema mexicanum, Hintonia latiflora and Hintonia standleyana. Based on a literature review very few articles have been published on MEGxp0_000947.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282204422D          

 32 35  0  0  1  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   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
   -2.8579    0.8250    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  5 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  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
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  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
   -6.1932   -2.1468    0.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9407   -2.0275    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3674   -0.8355    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9809   -0.6654    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692    0.5770    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5226    0.5990    1.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190    1.7923    2.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921    2.9636    1.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5965    4.1726    1.8684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    2.9516    0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2838    4.1388   -0.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260    1.7470   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943   -1.7431   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -1.6738   -0.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -0.5091   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -0.2089   -0.3623 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6944    0.0735    0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    0.0039    0.6149 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8812   -0.1948    1.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7450    0.8033    2.7896 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.2007   -0.1832 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8151    1.2963   -0.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7816    1.0571   -1.5564 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1423    2.0703   -2.4066 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    0.9703   -1.3049 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6244    0.6964   -2.4842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2829   -2.7788   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198   -3.9559   -1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -5.0345   -1.9073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2709   -4.0130   -1.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9351   -2.9160   -0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2350   -3.0065   -0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9404   -0.0078    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.2803    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510    1.8441    2.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0275    4.1716    2.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922    4.2001   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    1.7787   -0.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6569   -1.0408   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -0.8944   -0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5277   -1.1525    2.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240   -0.3906    1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8080    0.4481    3.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837    2.1526    0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9572    1.9809   -1.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    0.0739   -1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219    2.9268   -1.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166    1.9064   -0.8585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200    0.4753   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823   -2.7670   -1.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6481   -5.8971   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954   -4.9318   -1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 31  2  0
 31 32  1  0
 32  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 31 30  1  0
 30 28  2  0
 28 29  1  0
 28 27  1  0
 16 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 18  1  0
 27 14  2  0
  4 13  1  0
 12  5  1  0
 20 43  1  0
 19 41  1  0
 19 42  1  0
 18 40  1  6
 16 39  1  6
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 30 52  1  0
 29 51  1  0
 27 50  1  0
 25 48  1  1
 26 49  1  0
 23 46  1  6
 24 47  1  0
 21 44  1  1
 22 45  1  0
M  END

  Mrv1652304282204422D          

 32 35  0  0  1  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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    2.0625    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   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
   -2.8579    0.8250    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  5 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  1  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
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3C(OC(=O)C=C3C3=CC=C(O)C(O)=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-15-18(27)19(28)20(29)21(32-15)31-14-5-9(23)4-13-17(14)10(6-16(26)30-13)8-1-2-11(24)12(25)3-8/h1-6,15,18-25,27-29H,7H2/t15-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
VAPVFWUBNBLVMB-CMWLGVBASA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
41.84593791200177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.43

> <JCHEM_LOGP>
-0.26577118700000013

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.089504068135467

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.739434841743234

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462647825

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
115.16929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2   19   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3                                                       
CONECT   10    5   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18    4   19   20                                                  
CONECT   19   18    1                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3C(OC(=O)C=C3C3=CC=C(O)C(O)=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-15-18(27)19(28)20(29)21(32-15)31-14-5-9(23)4-13-17(14)10(6-16(26)30-13)8-1-2-11(24)12(25)3-8/h1-6,15,18-25,27-29H,7H2/t15-,18-,19+,20-,21-/m1/s1

InChI Key

VAPVFWUBNBLVMB-CMWLGVBASA-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
Coutarea hexandra	Plant	KNApSAcK
Exostema mexicanum	LOTUS Database	35616633
Hintonia latiflora	LOTUS Database	35616633
Hintonia standleyana	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-5-o-glycoside
Coumarin o-glycoside
4-phenylcoumarin
Neoflavonoid skeleton
Phenolic glycoside
7-hydroxycoumarin
Hexose monosaccharide
Hydroxycoumarin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Lactone
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organooxygen compound
Organic oxygen 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	0.43	ALOGPS
logP	-0.27	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.17 m³·mol⁻¹	ChemAxon
Polarizability	41.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

22913103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14134093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside (NP0057202)

MOL for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

3D MOL for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

3D SDF for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

3D-SDF for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

PDB for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

3D PDB for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

SMILES for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

INCHI for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

Structure for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)

3D Structure for NP0057202 (5,7,3',4'-Tetrahydroxy-4-phenylcoumarin 5-O-glucoside)