NP-MRD: Showing NP-Card for dihydroxybergamottin (NP0294317)

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Record Information

Version

2.0

Created at

2022-09-10 02:48:03 UTC

Updated at

2022-09-10 02:48:03 UTC

NP-MRD ID

NP0294317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroxybergamottin

Description

Dihydroxybergamottin, also known as 6,7-DHB, 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. dihydroxybergamottin is found in Citrus hystrix. dihydroxybergamottin was first documented in 2021 (PMID: 33947307). Based on a literature review a small amount of articles have been published on Dihydroxybergamottin (PMID: 35677541) (PMID: 34979453) (PMID: 34080214) (PMID: 33719319).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102204482D          

 27 29  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   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
    2.1434   -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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    5.4730    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 13 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    0.8714    0.8560   -1.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    1.3541   -0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0666    0.8965    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9996   -0.0747   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448    0.5119    0.1811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4671   -0.0341   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    0.1116   -1.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451    0.7353   -2.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9143    0.5300   -3.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7990   -0.1860   -2.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3839   -0.4625   -1.4093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9657   -1.1733   -0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3309   -1.3300    0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8840   -2.0084    1.7899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906   -2.1694    2.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8335   -2.8286    3.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0567   -1.6265    3.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4501   -0.9094    2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0822   -0.7517    0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909    2.3160   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3938    1.8124   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5871    0.5446    0.5034 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7277   -0.4786    0.1202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000    0.0208    0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780   -1.1641    1.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198   -0.5156   -0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    0.9997    0.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112    1.2043   -2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575   -0.2375   -1.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6447    1.2931   -2.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1103    1.2440    1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115   -1.0003    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9142   -0.2331   -1.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428    1.2760   -2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0212    0.8904   -4.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9518   -1.6152   -0.5506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5517   -1.7476    4.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762   -0.4613    2.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742    3.2468   -0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391    2.5768    0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0729    2.5719    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6771    1.7153   -1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3548    0.7631    1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9822   -0.8670   -0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1590   -1.2677    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -0.8951    2.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6960   -2.0411    0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8895   -1.5522   -0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063    0.1391   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4166   -0.6354   -1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4922    0.6565    1.5422 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
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  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
 19  6  1  0
 11  7  1  0
 14 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  1
 23 44  1  0
 25 45  1  0
 25 46  1  0
 25 47  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 27 51  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  8 34  1  0
  9 35  1  0
 12 36  1  0
 18 38  1  0
 17 37  1  0
M  END


  Mrv1652309102204482D          

 27 29  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   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
    2.1434   -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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    5.4730    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 13 19  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC[C@@H](O)C(C)(C)O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+/t18-/m1/s1

> <INCHI_KEY>
IXZUPBUEKFXTSD-INMULRNOSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.417

> <EXACT_MASS>
372.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.75441645646511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

> <JCHEM_LOGP>
2.665333304333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.321397485048589

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.842452032303402

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8325240439758224

> <JCHEM_POLAR_SURFACE_AREA>
89.13000000000001

> <JCHEM_REFRACTIVITY>
102.1213

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.771  12.884   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.231  10.216   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    6   13                                                  
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
6,7-DHB	MeSH
6',7'-Dihydroxybergamottin	MeSH

Chemical Formula

C₂₁H₂₄O₆

Average Mass

372.4170 Da

Monoisotopic Mass

372.15729 Da

IUPAC Name

4-{[(2E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

4-{[(2E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-en-1-yl]oxy}furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

C\C(CC[C@@H](O)C(C)(C)O)=C/COC1=C2C=COC2=CC2=C1C=CC(=O)O2

InChI Identifier

InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+/t18-/m1/s1

InChI Key

IXZUPBUEKFXTSD-INMULRNOSA-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
Citrus hystrix	LOTUS Database	35616633

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
Fatty alcohol
Alkyl aryl ether
Pyranone
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Tertiary alcohol
Furan
1,2-diol
Secondary alcohol
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furanocoumarin (CHEBI:70475 )

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	2.67	ChemAxon
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.12 m³·mol⁻¹	ChemAxon
Polarizability	39.75 Å³	ChemAxon
Number of Rings	3	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

C00047681

Chemspider ID

24657824

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

6',7'-Dihydroxybergamottin

METLIN ID

Not Available

PubChem Compound

12082365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han L, Cheng Y, Zhang T, Zhou Q, Zhang W, Li Y, Li G: Targeted Metabolomics With a Chemometric Study of Oxygenated Heterocyclic Aglycones as a Tool for Preliminary Authenticity Assessment of Orange and Grapefruit Juices. Front Nutr. 2022 May 23;9:897982. doi: 10.3389/fnut.2022.897982. eCollection 2022. [PubMed:35677541 ]
Akiyoshi T, Uchiyama M, Inada R, Imaoka A, Ohtani H: Analysis of inhibition kinetics of three beverage ingredients, bergamottin, dihydroxybergamottin and resveratrol, on CYP2C9 activity. Drug Metab Pharmacokinet. 2022 Feb;42:100429. doi: 10.1016/j.dmpk.2021.100429. Epub 2021 Nov 3. [PubMed:34979453 ]
Zhang Y, Yu Y, Li H, Huang W, Wang P: Effects of Citri Reticulatae Pericarpium and grapefruit juice on the pharmacokinetics of omeprazole in rats. J Food Biochem. 2022 Mar;46(3):e13804. doi: 10.1111/jfbc.13804. Epub 2021 Jun 2. [PubMed:34080214 ]
Ueno T, Takahashi S, Nakamura T, Tanaka Y, Hori H, Mizoi K, Ogihara T: Evaluation system for cell-permeable CYP3A4 inhibitory activity using 1alpha,25-dihydroxy-vitamin D(3)-induced intestinal cell lines. Xenobiotica. 2021 Jul;51(7):771-777. doi: 10.1080/00498254.2021.1925375. Epub 2021 May 17. [PubMed:33947307 ]
Garcia-Lor A, Bermejo A, Morales J, Hernandez M, Medina A, Cuenca J, Navarro L, Aleza P: Strategies to Produce Grapefruit-Like Citrus Varieties With a Low Furanocoumarin Content and Distinctive Flavonoid Profiles. Front Plant Sci. 2021 Feb 24;12:640512. doi: 10.3389/fpls.2021.640512. eCollection 2021. [PubMed:33719319 ]
LOTUS database [Link]

Showing NP-Card for dihydroxybergamottin (NP0294317)

MOL for NP0294317 (dihydroxybergamottin)

3D MOL for NP0294317 (dihydroxybergamottin)

3D SDF for NP0294317 (dihydroxybergamottin)

3D-SDF for NP0294317 (dihydroxybergamottin)

PDB for NP0294317 (dihydroxybergamottin)

3D PDB for NP0294317 (dihydroxybergamottin)

SMILES for NP0294317 (dihydroxybergamottin)

INCHI for NP0294317 (dihydroxybergamottin)

Structure for NP0294317 (dihydroxybergamottin)

3D Structure for NP0294317 (dihydroxybergamottin)