NP-MRD: Showing NP-Card for 3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid (NP0166088)

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Record Information

Version

2.0

Created at

2022-09-03 01:23:43 UTC

Updated at

2022-09-03 01:23:43 UTC

NP-MRD ID

NP0166088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid

Description

Puerarin malonyl ester belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. 3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid is found in Pueraria montana. Based on a literature review very few articles have been published on Puerarin malonyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032203232D          

 36 39  0  0  1  0            999 V2000
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5749   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
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 12 30  2  0  0  0  0
 17 30  1  0  0  0  0
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 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    3.6652    2.9966    1.4920 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    3.0742    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6511    3.0436    0.4077 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5711    0.9127   -1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672   -0.3634   -2.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233   -1.2060   -1.1709 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3672   -0.9084   -0.6601 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722   -1.4157    0.5761 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2362   -1.0260    1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3764   -1.3377    2.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -1.9706    3.3778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -0.9963    3.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287   -0.3436    3.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8546   -0.0309    1.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750    0.6259    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8829    0.9337    2.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227    0.9382    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343    1.5216   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3498    2.6706   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5429    3.1789   -1.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7186    2.5109   -1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8934    3.0003   -1.8999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7233    1.3494   -0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5435    0.8650   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0659    0.5567   -0.6627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074   -0.0644   -0.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802   -0.3605    1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -2.9262    0.5791 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9194   -3.6564    1.5438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9315   -3.1721    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3346   -4.4608    0.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -2.6416   -1.2388 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3337   -2.7508   -1.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1850    2.3534    0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8742    4.0413   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834    3.3627   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5202   -0.3394   -3.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1117   -0.8762   -2.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -0.8445   -0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   -1.0252    1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2951   -2.1351    2.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4618   -1.2740    4.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -0.0693    3.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4549    3.2453   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5426    4.0899   -2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5305    3.6370   -1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7044    0.8578   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5850   -0.0442    0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866    0.8125   -1.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9503   -3.2173   -0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013   -4.5698    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5669   -2.4538    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0036   -4.8085    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3836   -3.2568   -1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9586   -2.8712   -0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 35  1  0
 35 36  1  0
 35  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
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  2  1  2  0
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 30 29  1  0
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 28 20  2  0
 20 18  1  0
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 31 33  1  0
 13 12  1  0
 27 21  1  0
 17 30  1  0
 34 56  1  0
 33 55  1  1
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 36 58  1  0
  9 42  1  1
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  4 38  1  0
  4 39  1  0
  3 37  1  0
 11 43  1  1
 31 53  1  6
 32 54  1  0
 28 52  1  0
 16 46  1  0
 15 45  1  0
 14 44  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
M  END


  Mrv1652309032203232D          

 36 39  0  0  1  0            999 V2000
    7.1447   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5749   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5749   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    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
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 29 30  1  0  0  0  0
 12 30  2  0  0  0  0
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 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0166088

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@H]([C@@H]1O)C1=C2OC=C(C(=O)C2=CC=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O12/c25-11-3-1-10(2-4-11)13-8-35-23-12(19(13)30)5-6-14(26)18(23)24-22(33)21(32)20(31)15(36-24)9-34-17(29)7-16(27)28/h1-6,8,15,20-22,24-26,31-33H,7,9H2,(H,27,28)/t15-,20-,21+,22-,24+/m1/s1

> <INCHI_KEY>
PYAAYMRVSVAOSO-OIQDKXCASA-N

> <FORMULA>
C24H22O12

> <MOLECULAR_WEIGHT>
502.428

> <EXACT_MASS>
502.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.89684450428821

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxan-2-yl]methoxy}propanoic acid

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
0.30647066266666645

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.030573575190586

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2360511535256573

> <JCHEM_PKA_STRONGEST_BASIC>
-3.645438417371456

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999994

> <JCHEM_REFRACTIVITY>
118.31590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0      13.337  -1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      14.670   0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      17.338   0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      22.673  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.340   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      24.006   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.674   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.007   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.007  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      30.675  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.675  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.008  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.342  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      34.676  -6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      32.008  -6.160   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.007  -3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      26.674  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      26.674  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      25.340  -3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      22.673  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   35                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   20   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   12   17                                                  
CONECT   31   11   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    9   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₂O₁₂

Average Mass

502.4280 Da

Monoisotopic Mass

502.11113 Da

IUPAC Name

3-oxo-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]oxan-2-yl]methoxy}propanoic acid

Traditional Name

3-oxo-3-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@H]([C@@H]1O)C1=C2OC=C(C(=O)C2=CC=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C24H22O12/c25-11-3-1-10(2-4-11)13-8-35-23-12(19(13)30)5-6-14(26)18(23)24-22(33)21(32)20(31)15(36-24)9-34-17(29)7-16(27)28/h1-6,8,15,20-22,24-26,31-33H,7,9H2,(H,27,28)/t15-,20-,21+,22-,24+/m1/s1

InChI Key

PYAAYMRVSVAOSO-OIQDKXCASA-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
Pueraria montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid c-glycosides. These are c-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 C-glycosides

Direct Parent

Isoflavonoid C-glycosides

Alternative Parents

Substituents

Isoflavonoid c-glycoside
Isoflavonoid-8-c-glycoside
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
Glycosyl compound
C-glycosyl compound
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Monosaccharide
Dicarboxylic acid or derivatives
Oxane
Pyran
1,3-dicarbonyl compound
Benzenoid
Heteroaromatic compound
1,2-diol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Polyol
Dialkyl ether
Ether
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	1.2	ALOGPS
logP	0.31	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	118.32 m³·mol⁻¹	ChemAxon
Polarizability	47.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

8499243

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10323780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid (NP0166088)

MOL for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

3D MOL for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

3D SDF for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

3D-SDF for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

PDB for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

3D PDB for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

SMILES for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

INCHI for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

Structure for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)

3D Structure for NP0166088 (3-oxo-3-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[7-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxan-2-yl]methoxy}propanoic acid)