NP-MRD: Showing NP-Card for (2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one (NP0270364)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 16:13:25 UTC

Updated at

2022-09-08 16:13:25 UTC

NP-MRD ID

NP0270364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

Description

Bavachinin belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position. (2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one is found in Cullen corylifolium. (2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one was first documented in 2021 (PMID: 34564803). Based on a literature review a significant number of articles have been published on Bavachinin (PMID: 35610002) (PMID: 35960342) (PMID: 34950022) (PMID: 34500594) (PMID: 34043345) (PMID: 33830528).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218132D          

 25 27  0  0  1  0            999 V2000
   -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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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 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
   -3.5724   -0.4125    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 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
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 17 25  1  0  0  0  0
  5 25  1  0  0  0  0
M  END

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -2.4432   -0.4010   -2.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966    0.2542   -1.6639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6933    0.6940   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    0.4450   -1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865    0.8453   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    1.5033    0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8510    1.7272    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375    1.3372    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3160    1.5970    0.8140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8724    0.3060    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9966   -0.2354    0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4363   -1.5365    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8181    0.4448   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103    1.8899    1.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828    2.8557    2.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.1545    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1435    0.9382   -0.0866 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1560   -0.1506   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7513   -1.4684   -0.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6497   -2.5099   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9968   -2.2680   -0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8711   -3.3476   -0.4503 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862   -0.9545   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4899    0.0947   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854    0.6290   -0.8073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848    0.2652   -3.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -1.3725   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989   -0.5279   -3.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1861   -0.0632   -2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0173    2.2446    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    2.2867    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430    1.9994   -0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -0.2085    2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -2.3440    1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5243   -1.6121    1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1557   -1.4944    2.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2416    0.7788   -0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6278   -0.2800   -0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2932    1.3739    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7090    1.7166    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873    0.1600    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5844    1.8652   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053   -1.6493    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269   -3.5553   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0837   -3.8206   -1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4418   -0.7377   -0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8289    1.1311   -0.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 25  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  8  3  1  0
 24 18  1  0
 25  5  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
M  END


  Mrv1652309082218132D          

 25 27  0  0  1  0            999 V2000
   -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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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 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
   -3.5724   -0.4125    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
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  1  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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 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
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 17 25  1  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1CC=C(C)C)C(=O)C[C@H](O2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-10,12,20,22H,5,11H2,1-3H3/t20-/m0/s1

> <INCHI_KEY>
VOCGSQHKPZSIKB-FQEVSTJZSA-N

> <FORMULA>
C21H22O4

> <MOLECULAR_WEIGHT>
338.403

> <EXACT_MASS>
338.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
37.023561691943236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
4.363134427333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.041726062788516

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.471664953620886

> <JCHEM_PKA_STRONGEST_BASIC>
-4.597059471464726

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
98.034

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   17    5                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₄

Average Mass

338.4030 Da

Monoisotopic Mass

338.15181 Da

IUPAC Name

(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1CC=C(C)C)C(=O)C[C@H](O2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H22O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-10,12,20,22H,5,11H2,1-3H3/t20-/m0/s1

InChI Key

VOCGSQHKPZSIKB-FQEVSTJZSA-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
Cullen corylifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

6-prenylated flavanones

Alternative Parents

Substituents

6-prenylated flavanone
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Monohydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Anisole
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.36	ChemAxon
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.03 m³·mol⁻¹	ChemAxon
Polarizability	37.02 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008248

Chemspider ID

8512670

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10337211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Darzi S, Mirzaei SA, Elahian F, Peymani A, Rahmani B, Pishkhan Dibazar S, Shirian S, Shakeri Chaleshtori L, Aali E: Improvement of cytotoxicity of mitoxantrone and daunorubicin by candidone, tephrosin, and bavachinin. Mol Biol Rep. 2021 Nov;48(11):7105-7111. doi: 10.1007/s11033-021-06700-7. Epub 2021 Sep 25. [PubMed:34564803 ]
Namiranian P, Sadatpour O, Azimzadeh Jamalkandi S, Hossein Ayati M, Karimi M: Antiviral Activity of Medicinal Plants against Human Coronavirus: a systematic scoping review of and experimentations. J Tradit Chin Med. 2022 Jun;42(3):332-343. doi: 10.19852/j.cnki.jtcm.2022.03.002. [PubMed:35610002 ]
Zhang W, Liu J, Li Y, Guo F: A bavachinin analog, D36, induces cell death by targeting both autophagy and apoptosis pathway in acute myeloid leukemia cells. Cancer Chemother Pharmacol. 2022 Sep;90(3):251-265. doi: 10.1007/s00280-022-04462-y. Epub 2022 Aug 12. [PubMed:35960342 ]
Guo Z, Li P, Wang C, Kang Q, Tu C, Jiang B, Zhang J, Wang W, Wang T: Five Constituents Contributed to the Psoraleae Fructus-Induced Hepatotoxicity via Mitochondrial Dysfunction and Apoptosis. Front Pharmacol. 2021 Dec 7;12:682823. doi: 10.3389/fphar.2021.682823. eCollection 2021. [PubMed:34950022 ]
Pai JT, Hsu MW, Leu YL, Chang KT, Weng MS: Induction of G2/M Cell Cycle Arrest via p38/p21(Waf1/Cip1)-Dependent Signaling Pathway Activation by Bavachinin in Non-Small-Cell Lung Cancer Cells. Molecules. 2021 Aug 25;26(17):5161. doi: 10.3390/molecules26175161. [PubMed:34500594 ]
Hung SY, Lin SC, Wang S, Chang TJ, Tung YT, Lin CC, Ho CT, Li S: Bavachinin Induces G2/M Cell Cycle Arrest and Apoptosis via the ATM/ATR Signaling Pathway in Human Small Cell Lung Cancer and Shows an Antitumor Effect in the Xenograft Model. J Agric Food Chem. 2021 Jun 9;69(22):6260-6270. doi: 10.1021/acs.jafc.1c01657. Epub 2021 May 27. [PubMed:34043345 ]
Shi GZ, Song D, Li PY, Chen SS, Zhang L, Li SS, Xiao XH, Qin XH, Wang JB: Screening of hepatotoxic compounds in Psoralea corylifolia L., a traditional Chinese herbal and dietary supplement, using high-resolution mass spectrometry and high-content imaging. Biomed Chromatogr. 2021 Sep;35(9):e5140. doi: 10.1002/bmc.5140. Epub 2021 Apr 27. [PubMed:33830528 ]
Mandal A, Jha AK, Hazra B: Plant Products as Inhibitors of Coronavirus 3CL Protease. Front Pharmacol. 2021 Mar 9;12:583387. doi: 10.3389/fphar.2021.583387. eCollection 2021. [PubMed:33767619 ]
Wei MM, Sun XY, Wu SY, Wang SY, Gao Y, Kang C, Yang W, Li YF, Li C: [Rapid and simultaneous determination of 10 active components of Psoraleae Fructus in beagle dog plasma using UPLC-MS/MS and its application in pharmacokinetic study]. Zhongguo Zhong Yao Za Zhi. 2021 Jan;46(2):444-453. doi: 10.19540/j.cnki.cjcmm.20200629.204. [PubMed:33645134 ]
Zhang C, Qin Q, Li H: Targeted Therapeutic Effect of Bavachinin Nanospheres on Pathological Site of Chronic Asthmatic Mice Model. J Nanosci Nanotechnol. 2021 Feb 1;21(2):1085-1090. doi: 10.1166/jnn.2021.18641. [PubMed:33183447 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one (NP0270364)

MOL for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0270364 ((2s)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)