NP-MRD: Showing NP-Card for 5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one (NP0310536)

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Record Information

Version

2.0

Created at

2022-09-11 05:54:48 UTC

Updated at

2022-09-11 05:54:48 UTC

NP-MRD ID

NP0310536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Apigenin-4'-glucoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one is found in Antennaria dioica, Artemisia judaica, Centaurea cyanus, Centaurea montana, Chaerophyllum aureum, Cinnamomum philippinense, Equisetum pratense, Gerbera jamesonii, Helichrysum armenium, Ixora finlaysoniana, Leonurus cardiaca, Machilus japonica, Macrothelypteris torresiana, Marrubium anisodon, Morina nepalensis, Phoradendron leucarpum, Phyllocladus hypophyllus, Picris hieracioides, Punica granatum, Saussurea medusa and Stevia rebaudiana. Apigenin-4'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304131800582D          

 31 34  0  0  0  0            999 V2000
10003.923410003.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.494410007.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.921610004.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.637310004.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.921610007.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.350910007.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.350910005.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.498710003.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.069810005.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.779910006.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.065510007.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.350910006.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.350910005.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.065410005.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.779910005.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.923910005.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.209410005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.209410004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.923910004.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.638310004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.638310005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.922310007.1548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.207910006.7423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.207910005.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.922310005.5049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10009.636810005.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10009.636810006.7423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.498110005.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783510005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783410004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.498010004.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  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
 15 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31  8  1  0  0  0  0
 29  9  1  0  0  0  0
 10  2  1  0  0  0  0
  1 19  2  0  0  0  0
 17 28  2  0  0  0  0
 31 18  2  0  0  0  0
 21 13  1  0  0  0  0
 22  5  1  6  0  0  0
 27  6  1  1  0  0  0
 26  7  1  6  0  0  0
 25  3  1  1  0  0  0
 23  2  1  1  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    6.2315    1.6575   -2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5046    1.0265   -1.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1164    1.1281   -1.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    0.4579   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8443    0.5628   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860   -0.1577    0.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3140   -0.0718    0.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877    0.6914   -0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514    0.7928   -0.5826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2487    0.1482    0.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9622   -0.7528   -0.5497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1878   -1.0271    0.0223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8307   -2.2627   -0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0690   -3.3931   -0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0689    0.1785   -0.3355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3980   -0.0572    0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4722    1.3553    0.3502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4877    2.4299   -0.5410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273    1.1472    0.9335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2479    0.7665    2.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059    1.4114   -1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    1.3324   -1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8812   -0.3137    0.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1817   -0.4403    0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7453   -1.2598    1.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1077   -1.4023    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5860   -2.2506    2.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9799   -0.7575    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4341    0.0802   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3325    0.6982   -0.9873 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0649    0.2210   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139    1.7763   -2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924   -0.7785    1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8434   -0.6673    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -0.4795    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0492   -1.1019    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8055   -2.4076   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0400   -2.0677   -1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6842   -4.1762   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9792    0.3138   -1.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9600    0.4179   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2059    1.6538    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7048    2.9807   -0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5966    2.1334    0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    1.1200    2.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.0248   -2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    1.9148   -2.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1009   -1.7973    2.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7148   -3.2260    2.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454   -0.8827    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3403    1.3099   -1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 22  1  0
 22 21  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 31  1  0
 31 29  2  0
 29 30  1  0
 29 28  1  0
 28 26  2  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 10 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 15  1  0
 15 16  1  0
 15 12  1  0
 21  8  1  0
 23  4  1  0
 24 31  1  0
 14 39  1  0
 13 37  1  0
 13 38  1  0
 12 36  1  1
 10 35  1  1
  7 34  1  0
  6 33  1  0
 22 47  1  0
 21 46  1  0
  3 32  1  0
 30 51  1  0
 28 50  1  0
 27 49  1  0
 25 48  1  0
 19 44  1  1
 20 45  1  0
 17 42  1  1
 18 43  1  0
 15 40  1  6
 16 41  1  0
M  END

  Mrv1652304131800582D          

 31 34  0  0  0  0            999 V2000
10003.923410003.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.494410007.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.921610004.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.637310004.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.921610007.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.350910007.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.350910005.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.498710003.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.069810005.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.779910006.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.065510007.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.350910006.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.350910005.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.065410005.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.779910005.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.923910005.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.209410005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.209410004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.923910004.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.638310004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.638310005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.922310007.1548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.207910006.7423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.207910005.9173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.922310005.5049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10009.636810005.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10009.636810006.7423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.498110005.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783510005.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.783410004.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.498010004.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  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
 15 10  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31  8  1  0  0  0  0
 29  9  1  0  0  0  0
 10  2  1  0  0  0  0
  1 19  2  0  0  0  0
 17 28  2  0  0  0  0
 31 18  2  0  0  0  0
 21 13  1  0  0  0  0
 22  5  1  6  0  0  0
 27  6  1  1  0  0  0
 26  7  1  6  0  0  0
 25  3  1  1  0  0  0
 23  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0310536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-3-1-9(2-4-11)14-7-13(25)17-12(24)5-10(23)6-15(17)30-14/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
ICLVCWSZHUZEFT-QNDFHXLGSA-N

> <FORMULA>
C21H20O10

> <MOLECULAR_WEIGHT>
432.381

> <EXACT_MASS>
432.105646844

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.551377061682814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.4386210403333334

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.180407716551963

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.577779430434239

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
105.0583

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-APR-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-APR-18         0                                  
HETATM    1  O   UNK     0    8673.9908673.074   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8680.6568680.019   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8683.3208675.401   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8684.6568674.632   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8683.3208681.559   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8685.9888680.019   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8685.9888676.940   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.3318673.074   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8668.6648677.714   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8679.3228679.252   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8677.9898680.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.6558679.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8676.6558677.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8677.9898676.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8679.3228677.712   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8673.9918677.705   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8672.6588676.935   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.6588675.395   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8673.9918674.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.3258675.395   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8675.3258676.935   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8683.3228680.022   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8681.9888679.252   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8681.9888677.712   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8683.3228676.942   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8684.6558677.712   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8684.6558679.252   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8671.3308677.705   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8669.9968676.935   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8669.9968675.395   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8671.3308674.625   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   10   23                                                       
CONECT    3    4   25                                                       
CONECT    4    3                                                            
CONECT    5   22                                                            
CONECT    6   27                                                            
CONECT    7   26                                                            
CONECT    8   31                                                            
CONECT    9   29                                                            
CONECT   10   11   15    2                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   17   21                                                       
CONECT   17   18   16   28                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20    1                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   13                                                  
CONECT   22   23   27    5                                                  
CONECT   23   22   24    2                                                  
CONECT   24   23   25                                                       
CONECT   25   26   24    3                                                  
CONECT   26   25   27    7                                                  
CONECT   27   22   26    6                                                  
CONECT   28   29   17                                                       
CONECT   29   28   30    9                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8   18                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Apigenin 4'-beta-glucopyranoside	HMDB
Apigenin 4'-O-beta-D-glucopyranoside	HMDB
Apigenin 4'-O-beta-D-glucoside	HMDB
Apigenin 4'-O-β-D-glucopyranoside	HMDB
Apigenin 4'-O-β-D-glucoside	HMDB
Apigenin 4'-β-glucopyranoside	HMDB
Apigenin-4'-glucoside	HMDB
4',5,7-Trihydroxyflavone 4'-beta-D-glucoside	HMDB
4',5,7-Trihydroxyflavone 4'-β-D-glucoside	HMDB
4'-O-beta-D-Glucopyranosylapigenin	HMDB
4'-O-beta-D-Glucosylapigenin	HMDB
4'-O-Β-D-glucopyranosylapigenin	HMDB
4'-O-Β-D-glucosylapigenin	HMDB
Apigenin 4'-beta-D-glucoside	HMDB
Apigenin 4'-glucoside	HMDB
Apigenin 4'-O-beta-glucopyranoside	HMDB
Apigenin 4'-O-beta-glucoside	HMDB
Apigenin 4'-O-β-glucopyranoside	HMDB
Apigenin 4'-O-β-glucoside	HMDB
Apigenin 4'-β-D-glucoside	HMDB

Chemical Formula

C₂₁H₂₀O₁₀

Average Mass

432.3810 Da

Monoisotopic Mass

432.10565 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C=C2)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-3-1-9(2-4-11)14-7-13(25)17-12(24)5-10(23)6-15(17)30-14/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1

InChI Key

ICLVCWSZHUZEFT-QNDFHXLGSA-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
Antennaria dioica	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Centaurea cyanus	LOTUS Database	35616633
Centaurea montana	LOTUS Database	35616633
Chaerophyllum aureum	LOTUS Database	35616633
Cinnamomum philippinense	LOTUS Database	35616633
Equisetum pratense	LOTUS Database	35616633
Gerbera jamesonii	LOTUS Database	35616633
Helichrysum armenium	LOTUS Database	35616633
Ixora finlaysoniana	LOTUS Database	35616633
Leonurus cardiaca	LOTUS Database	35616633
Machilus japonica	LOTUS Database	35616633
Macrothelypteris torresiana	LOTUS Database	35616633
Marrubium anisodon	LOTUS Database	35616633
Morina nepalensis	LOTUS Database	35616633
Phoradendron leucarpum	LOTUS Database	35616633
Phyllocladus hypophyllus	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
Flavonoid-4p-o-glycoside
Hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
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	0.8	ALOGPS
logP	0.44	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.06 m³·mol⁻¹	ChemAxon
Polarizability	42.55 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

HMDB0041591

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5491384

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one (NP0310536)

MOL for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D MOL for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D SDF for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D-SDF for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

PDB for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D PDB for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

SMILES for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

INCHI for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

Structure for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)

3D Structure for NP0310536 (5,7-dihydroxy-2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one)