NP-MRD: Showing NP-Card for Epoxybergamottin (NP0083965)

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Record Information

Version

2.0

Created at

2022-04-29 04:50:52 UTC

Updated at

2022-04-29 04:50:52 UTC

NP-MRD ID

NP0083965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epoxybergamottin

Description

Epoxybergamottin belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Thus, epoxybergamottin is considered to be a flavonoid. Epoxybergamottin is found in Citrus aurantium, Citrus maxima and Citrus paradisi . Epoxybergamottin was first documented in 2017 (PMID: 28911545). Based on a literature review a small amount of articles have been published on Epoxybergamottin (PMID: 32221600) (PMID: 30236679) (PMID: 28598384) (PMID: 28322044).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206502D          

 26 29  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    5.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    5.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  2  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
 19 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    1.3243   -1.3757   -2.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0261   -1.0998   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829   -1.4517   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.0865   -1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3979   -1.3989   -1.3023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579   -1.0530   -0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1911   -2.0298    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639   -3.3032   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5062   -3.7575    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8509   -2.8272    1.2084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0841   -1.7577    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0386   -0.5379    1.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1037    0.4267    1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0551    1.5791    1.9685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    2.5072    1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495    3.5864    2.3208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2496    2.3354    0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2607    1.1317   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1867    0.1751    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587   -0.4668    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.9076   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5158    1.4335    0.5338 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6823    0.5104    0.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7889    1.8849    0.2074 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5905    2.6434    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433    2.1314   -1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471   -1.0448   -2.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -2.4663   -2.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -0.8171   -2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4173   -1.2613    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7991   -2.2798   -2.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450   -3.0679   -0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9065   -3.7914   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9635   -4.7473    0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7451   -0.3338    2.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5714    3.1483    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5614    0.9475   -0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7767   -0.3358    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0038   -1.0715    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6044    1.5902   -0.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    0.8404   -1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1055    1.5609    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1853    3.4667    0.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    3.0122    2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3500    1.9740    1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0648    1.3867   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6761    3.1670   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4137    2.0160   -1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 19  2  0
 19 18  1  0
 18 17  2  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 24 22  1  0
 19  6  1  0
 11  7  1  0
 14 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  1
 25 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 26 48  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
 12 35  1  0
 18 37  1  0
 17 36  1  0
M  END


  Mrv1652304292206502D          

 26 29  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    5.9997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357    5.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  6 19  2  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
 19 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 25  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCC1OC1(C)C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O5/c1-13(4-6-18-21(2,3)26-18)8-10-24-20-14-5-7-19(22)25-17(14)12-16-15(20)9-11-23-16/h5,7-9,11-12,18H,4,6,10H2,1-3H3/b13-8+

> <INCHI_KEY>
OOKSPQLCQUBEKU-MDWZMJQESA-N

> <FORMULA>
C21H22O5

> <MOLECULAR_WEIGHT>
354.402

> <EXACT_MASS>
354.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
38.57494556308613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
4.91

> <JCHEM_LOGP>
3.8270368766666665

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.81517855946711

> <JCHEM_POLAR_SURFACE_AREA>
61.2

> <JCHEM_REFRACTIVITY>
98.61120000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.566   9.804   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.106   9.804   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.757  11.199   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.640   9.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    6   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   19   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25    5   24   26                                                  
CONECT   26   25    2                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₅

Average Mass

354.4020 Da

Monoisotopic Mass

354.14672 Da

IUPAC Name

4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

4-{[(2E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

C\C(CCC1OC1(C)C)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C21H22O5/c1-13(4-6-18-21(2,3)26-18)8-10-24-20-14-5-7-19(22)25-17(14)12-16-15(20)9-11-23-16/h5,7-9,11-12,18H,4,6,10H2,1-3H3/b13-8+

InChI Key

OOKSPQLCQUBEKU-MDWZMJQESA-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
Citrus aurantium	LOTUS Database	35616633
Citrus maxima	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Other Flavonoids (LMPK12160610 )

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	4.91	ALOGPS
logP	3.83	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.61 m³·mol⁻¹	ChemAxon
Polarizability	38.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00053039

Chemspider ID

8122237

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9946625

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun W, Rice MS, Park MK, Chun OK, Melough MM, Nan H, Willett WC, Li WQ, Qureshi AA, Cho E: Intake of Furocoumarins and Risk of Skin Cancer in 2 Prospective US Cohort Studies. J Nutr. 2020 Jun 1;150(6):1535-1544. doi: 10.1093/jn/nxaa062. [PubMed:32221600 ]
Li GJ, Wu HJ, Wang Y, Hung WL, Rouseff RL: Determination of citrus juice coumarins, furanocoumarins and methoxylated flavones using solid phase extraction and HPLC with photodiode array and fluorescence detection. Food Chem. 2019 Jan 15;271:29-38. doi: 10.1016/j.foodchem.2018.07.130. Epub 2018 Jul 21. [PubMed:30236679 ]
Hung WL, Suh JH, Wang Y: Chemistry and health effects of furanocoumarins in grapefruit. J Food Drug Anal. 2017 Jan;25(1):71-83. doi: 10.1016/j.jfda.2016.11.008. Epub 2016 Dec 6. [PubMed:28911545 ]
Kuo PC, Liao YR, Hung HY, Chuang CW, Hwang TL, Huang SC, Shiao YJ, Kuo DH, Wu TS: Anti-Inflammatory and Neuroprotective Constituents from the Peels of Citrus grandis. Molecules. 2017 Jun 9;22(6):967. doi: 10.3390/molecules22060967. [PubMed:28598384 ]
Melough MM, Vance TM, Lee SG, Provatas AA, Perkins C, Qureshi A, Cho E, Chun OK: Furocoumarin Kinetics in Plasma and Urine of Healthy Adults Following Consumption of Grapefruit (Citrus paradisi Macf.) and Grapefruit Juice. J Agric Food Chem. 2017 Apr 12;65(14):3006-3012. doi: 10.1021/acs.jafc.7b00317. Epub 2017 Mar 29. [PubMed:28322044 ]

Showing NP-Card for Epoxybergamottin (NP0083965)

MOL for NP0083965 (Epoxybergamottin)

3D MOL for NP0083965 (Epoxybergamottin)

3D SDF for NP0083965 (Epoxybergamottin)

3D-SDF for NP0083965 (Epoxybergamottin)

PDB for NP0083965 (Epoxybergamottin)

3D PDB for NP0083965 (Epoxybergamottin)

SMILES for NP0083965 (Epoxybergamottin)

INCHI for NP0083965 (Epoxybergamottin)

Structure for NP0083965 (Epoxybergamottin)

3D Structure for NP0083965 (Epoxybergamottin)