NP-MRD: Showing NP-Card for (-)-Pseudosemiglabrin (NP0059862)

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Record Information

Version

2.0

Created at

2022-04-28 05:01:20 UTC

Updated at

2022-04-28 05:01:20 UTC

NP-MRD ID

NP0059862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Pseudosemiglabrin

Description

Pseudosemiglabrin belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position. Thus, pseudosemiglabrin is considered to be a flavonoid. (-)-Pseudosemiglabrin is found in Tephrosia nubica, Tephrosia purpurea and Tephrosia semiglabra. (-)-Pseudosemiglabrin was first documented in 2016 (PMID: 27553975). Based on a literature review a small amount of articles have been published on Pseudosemiglabrin (PMID: 32922290) (PMID: 32581814) (PMID: 32878453).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207012D          

 29 33  0  0  1  0            999 V2000
    0.6114   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -1.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -0.8542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5121   -0.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8600    0.4559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6789    0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -0.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4650    0.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    2.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    0.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    0.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226    2.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.7295    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  3  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -2.6669    2.4471    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0934    1.3727   -0.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5124    1.6896   -1.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1575    0.0227   -0.3687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5995   -0.9759   -1.2025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5689   -1.8034   -0.5345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2717   -1.4234    0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504   -2.1140    1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580   -1.9972    3.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458   -1.1546    3.6001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6495   -0.4467    2.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    0.3842    3.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    0.4941    4.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262    1.0796    2.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4018    0.9362    1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139    1.6464    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    1.4684   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1006    2.1253   -1.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0469    2.9948   -1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1241    3.1864    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2446    2.5011    0.9211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5060    0.1108    0.7678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.5796    1.4454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854   -2.9082    0.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795   -3.1273   -0.3439 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1392   -3.2303   -1.4045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070   -1.9564   -1.6937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9105   -1.6768   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253   -1.8468   -3.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6254    2.8003   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170    3.3509    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096    2.1085    1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410   -0.4760   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -2.0109   -1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8398   -2.5311    3.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2255   -1.0394    4.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1378    1.7369    3.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    0.7958   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0808    2.0094   -2.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7346    3.5309   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633    3.8634    0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    2.7136    1.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -3.9626   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568   -1.0368   -1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904   -1.0959    0.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -2.6146   -0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.9807   -3.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936   -1.6265   -3.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3014   -2.7542   -3.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 25  1  0
 25 24  1  0
 24  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 22  1  0
 22 23  1  0
 23  7  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 27  5  1  0
  7  6  1  0
 21 16  1  0
  7  8  1  0
 23 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  6
  6 34  1  6
 25 43  1  1
  9 35  1  0
 10 36  1  0
 14 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 21 42  1  0
 28 44  1  0
 28 45  1  0
 28 46  1  0
 29 47  1  0
 29 48  1  0
 29 49  1  0
M  END


  Mrv1652304282207012D          

 29 33  0  0  1  0            999 V2000
    0.6114   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0107   -0.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -2.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -1.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -1.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161   -0.8542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5121   -0.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8600    0.4559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6789    0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372   -0.4534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8720    1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4650    0.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    1.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833    1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    2.6057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7082    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1477    0.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    0.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137   -1.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0863    1.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4643    2.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226    2.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    3.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    1.7295    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9  3  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H]2[C@@H](OC3=CC=C4C(=O)C=C(OC4=C23)C2=CC=CC=C2)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21+,22+/m1/s1

> <INCHI_KEY>
XTIQPKJOGKMOSY-HJNYFJLDSA-N

> <FORMULA>
C23H20O6

> <MOLECULAR_WEIGHT>
392.407

> <EXACT_MASS>
392.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.30312473125795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,15S,16R)-14,14-dimethyl-6-oxo-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-15-yl acetate

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.2300467590000013

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.749052652625576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.259089322321807

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
104.5295

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,15S,16R)-14,14-dimethyl-6-oxo-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-15-yl acetate

> <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       1.141  -1.805   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.020  -0.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.477  -1.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.772  -2.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.611  -3.817   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.846  -3.317   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.301  -2.991   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.950  -1.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.823  -0.546   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.472   0.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.001   0.665   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.296  -0.846   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.361   2.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.468   1.132   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.724   2.197   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.516   3.518   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.767   4.864   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.055   3.493   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.276   0.718   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.732   1.217   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.893   0.206   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.598  -1.306   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.759  -2.317   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.028   2.729   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.867   3.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.162   5.252   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.619   5.751   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.780   4.740   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.484   3.228   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11    8                                                       
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    1   23                                                  
CONECT   23   22                                                            
CONECT   24   20   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
Pseudosemiglabrin, (7aalpha,10alpha,10aalpha)-(-)-isomer	MeSH
Semiglabrin	MeSH

Chemical Formula

C₂₃H₂₀O₆

Average Mass

392.4070 Da

Monoisotopic Mass

392.12599 Da

IUPAC Name

(12S,15S,16R)-14,14-dimethyl-6-oxo-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-15-yl acetate

Traditional Name

(12S,15S,16R)-14,14-dimethyl-6-oxo-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.0^{2,7}.0^{12,16}]hexadeca-1,4,7,9-tetraen-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H]2[C@@H](OC3=CC=C4C(=O)C=C(OC4=C23)C2=CC=CC=C2)OC1(C)C

InChI Identifier

InChI=1S/C23H20O6/c1-12(24)26-21-19-18-16(28-22(19)29-23(21,2)3)10-9-14-15(25)11-17(27-20(14)18)13-7-5-4-6-8-13/h4-11,19,21-22H,1-3H3/t19-,21+,22+/m1/s1

InChI Key

XTIQPKJOGKMOSY-HJNYFJLDSA-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
Tephrosia nubica	Plant	KNApSAcK
Tephrosia purpurea	LOTUS Database	35616633
Tephrosia semiglabra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

8-prenylated flavones

Alternative Parents

Substituents

8-prenylated flavone
Chromone
Benzopyran
1-benzopyran
Coumaran
Pyranone
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Pyran
Heteroaromatic compound
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110018 )

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	3.92	ALOGPS
logP	3.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.75	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.53 m³·mol⁻¹	ChemAxon
Polarizability	40.3 Å³	ChemAxon
Number of Rings	5	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

C00013467

Chemspider ID

8583623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10408186

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mahmoud AB, Danton O, Kaiser M, Khalid S, Hamburger M, Maser P: HPLC-Based Activity Profiling for Antiprotozoal Compounds in Croton gratissimus and Cuscuta hyalina. Front Pharmacol. 2020 Aug 14;11:1246. doi: 10.3389/fphar.2020.01246. eCollection 2020. [PubMed:32922290 ]
Mahmoud AB, Maser P, Kaiser M, Hamburger M, Khalid S: Mining Sudanese Medicinal Plants for Antiprotozoal Agents. Front Pharmacol. 2020 Jun 9;11:865. doi: 10.3389/fphar.2020.00865. eCollection 2020. [PubMed:32581814 ]
Sallam A, Mira A, Sabry MA, Abdel-Halim OB, Gedara SR, Galala AA: New prenylated flavonoid and neuroprotective compounds from Tephrosia purpurea subsp. dunensis. Nat Prod Res. 2021 Dec;35(24):5612-5620. doi: 10.1080/14786419.2020.1815739. Epub 2020 Sep 2. [PubMed:32878453 ]
Hassan LE, Dahham SS, Fadul SM, Umar MI, Majid AS, Khaw KY, Majid AM: Evaluation of in vitro and in vivo anti-inflammatory effects of (-)-pseudosemiglabrin, a major phytoconstituent isolated from Tephrosia apollinea (Delile) DC. J Ethnopharmacol. 2016 Dec 4;193:312-320. doi: 10.1016/j.jep.2016.08.023. Epub 2016 Aug 20. [PubMed:27553975 ]

Showing NP-Card for (-)-Pseudosemiglabrin (NP0059862)

MOL for NP0059862 ((-)-Pseudosemiglabrin)

3D MOL for NP0059862 ((-)-Pseudosemiglabrin)

3D SDF for NP0059862 ((-)-Pseudosemiglabrin)

3D-SDF for NP0059862 ((-)-Pseudosemiglabrin)

PDB for NP0059862 ((-)-Pseudosemiglabrin)

3D PDB for NP0059862 ((-)-Pseudosemiglabrin)

SMILES for NP0059862 ((-)-Pseudosemiglabrin)

INCHI for NP0059862 ((-)-Pseudosemiglabrin)

Structure for NP0059862 ((-)-Pseudosemiglabrin)

3D Structure for NP0059862 ((-)-Pseudosemiglabrin)