NP-MRD: Showing NP-Card for Pomiferin (NP0051485)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:59 UTC

Updated at

2022-04-27 22:49:59 UTC

NP-MRD ID

NP0051485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pomiferin

Description

Pomiferin belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, pomiferin is considered to be a flavonoid lipid molecule. The mechanism for this protection may occur through the inhibition of lipid peroxidation. Pomiferin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Pomiferin is a prenylated isoflavone that can be found along with osajin in the fruits and female flowers of the osage orange tree (Maclura pomifera). Mahmoud (1981) indicated that pomiferin exhibited antibacterial activity against E. Coli and Salmonella gallinarum, as well as Mycobacterium smegmatis to a lesser extent. In 1941, Wolfram classified pomiferin as an isoflavone and in 1946 published the complete structure of Pomiferin. Anti-cancer activity Svasti (2005) observed that pomiferin induced apoptosis and differentiation in cholangiocarcinoma cell line HuCCA-1. Pomiferin has shown antioxidant activity via inhibition of lipid peroxidation and the reduction of free radicals, reactive oxygen species and other unstable molecules. Peterson and Fristad (2000) investigated folklore beliefs stating that osage orange fruit repelled insects. Pomiferin is found in Aloe vera , Arabidopsis thaliana, Bupleurum scorzonerifolium , Erycibe expansa , Erythroxylum ulei, Acca sellowiana, Flemingia macrophylla, Maclura pomifera, Millettia pachycarpa and Sarcolobus globosus. Pomiferin exhibited cytotoxicity effects on six cancer cells lines: Kidney (ACHN), Lung (NCI-H23), Prostate (PC-3), Breast (MDA-MB-231), Melanoma (LOX-IMVI) and Colon (HCT-15).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171521532D          

 31 34  0  0  0  0            999 V2000
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    3.9849    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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 15 22  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.1395   -3.6426   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9533   -2.5794   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1389   -1.7674   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -2.4431   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605   -1.4471    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3794   -0.4996    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.7620    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6678    1.5889   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6572    1.1871   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815    2.0684   -0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418    1.7154   -0.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.4636   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6559    0.0575   -0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6448    0.8668    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9803    0.5318    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3751   -0.6745   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7227   -1.0574   -0.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159   -1.5297   -0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8009   -2.7589   -1.1332 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0861   -1.1663   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -0.4518    0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -1.5846    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668   -0.0966    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -0.9487    0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -2.2198    1.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9561    2.9565   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2176    3.3485   -0.6200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    2.4968   -0.2324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3604    2.3708   -1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0231    3.2005    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0299    1.2125    0.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2055   -3.7218   -1.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -4.5797   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4981   -3.3465   -2.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2597   -0.8613   -0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1706   -1.4925    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0309   -2.4515   -0.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9506   -3.0751   -0.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0356   -1.9492    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3192   -0.8306    1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223    2.4085   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3662    1.8280    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7207    1.2231    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3995   -0.4215    0.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7770   -3.0300   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446   -1.8465   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9525   -2.8007    1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    3.6152   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    4.3476   -0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7545    2.1681   -2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9683    3.2897   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9653    1.4727   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7562    3.9324    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133    2.4775    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2985    3.6846    1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 24  2  0
 24 25  1  0
 24 23  1  0
 23  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 21  1  0
 21 22  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  9  8  1  0
  8  7  2  0
  7 31  1  0
 31 28  1  0
 28 29  1  6
 28 30  1  0
 28 27  1  0
 27 26  2  0
  7  6  1  0
 21 23  1  0
 20 13  1  0
 26  8  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
 25 47  1  0
 11 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 30 53  1  0
 30 54  1  0
 30 55  1  0
 27 49  1  0
 26 48  1  0
M  END


  Mrv1533004171521532D          

 31 34  0  0  0  0            999 V2000
   -0.9355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    3.9849    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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 15 22  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 23 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=CC=C(O)C(O)=C2)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O6/c1-13(2)5-7-15-21(28)20-22(29)17(14-6-8-18(26)19(27)11-14)12-30-24(20)16-9-10-25(3,4)31-23(15)16/h5-6,8-12,26-28H,7H2,1-4H3

> <INCHI_KEY>
GHCZYXUOYFOXIP-UHFFFAOYSA-N

> <FORMULA>
C25H24O6

> <MOLECULAR_WEIGHT>
420.461

> <EXACT_MASS>
420.157288493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
46.00013740611462

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.706062791000001

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.695319060652839

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.35784172089196

> <JCHEM_PKA_STRONGEST_BASIC>
-4.805515401250038

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
120.3191

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pomiferin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.386  -0.220   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.386   1.760   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.564   2.104   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.564   7.438   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21    5   15                                                  
CONECT   23   11   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-(3,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-4H,8H-pyrano(2,3-H)chromen-4-one	MeSH

Chemical Formula

C₂₅H₂₄O₆

Average Mass

420.4610 Da

Monoisotopic Mass

420.15729 Da

IUPAC Name

3-(3,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

pomiferin

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=CC=C(O)C(O)=C2)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C25H24O6/c1-13(2)5-7-15-21(28)20-22(29)17(14-6-8-18(26)19(27)11-14)12-30-24(20)16-9-10-25(3,4)31-23(15)16/h5-6,8-12,26-28H,7H2,1-4H3

InChI Key

GHCZYXUOYFOXIP-UHFFFAOYSA-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
Aloe vera	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Bupleurum scorzonerifolium	Plant	KNApSAcK
Erycibe expansa	Plant	KNApSAcK
Erythroxylum ulei	Plant	KNApSAcK
Feijoa sellowiana	Plant	KNApSAcK
Flemingia macrophylla	LOTUS Database	35616633
Maclura pomifera	Plant	KNApSAcK
Millettia pachycarpa	LOTUS Database	35616633
Sarcolobus globosus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Pyranoisoflavonoid
Isoflavone
Hydroxyisoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Catechol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (CHEBI:8329 )
isoflavones (C10519 )
Isoflavonoids (C10519 )
Isoflavonoids (LMPK12050244 )

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	5.01	ALOGPS
logP	5.71	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	7.36	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	120.32 m³·mol⁻¹	ChemAxon
Polarizability	46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00002562

Chemspider ID

Not Available

KEGG Compound ID

C10519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pomiferin

METLIN ID

Not Available

PubChem Compound

4871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pomiferin (NP0051485)

MOL for NP0051485 (Pomiferin)

3D MOL for NP0051485 (Pomiferin)

3D SDF for NP0051485 (Pomiferin)

3D-SDF for NP0051485 (Pomiferin)

PDB for NP0051485 (Pomiferin)

3D PDB for NP0051485 (Pomiferin)

SMILES for NP0051485 (Pomiferin)

INCHI for NP0051485 (Pomiferin)

Structure for NP0051485 (Pomiferin)

3D Structure for NP0051485 (Pomiferin)