NP-MRD: Showing NP-Card for juglanin a (NP0240999)

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Record Information

Version

2.0

Created at

2022-09-07 00:57:21 UTC

Updated at

2022-09-07 00:57:21 UTC

NP-MRD ID

NP0240999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

juglanin a

Description

Juglanin A belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring. Juglanin A is an extremely weak basic (essentially neutral) compound (based on its pKa). juglanin a is found in Juglans regia. juglanin a was first documented in 2008 (PMID: 18343385). A cyclic ketone isolated from the extract of the seed husks of walnuts Juglans regia and has been shown to exhibit cytotoxic activity against human hepatoma cells (PMID: 18496782) (PMID: 18771874) (PMID: 21157684).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514592D          

 26 28  0  0  0  0            999 V2000
    1.5321   -3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -2.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -1.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -0.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085    0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358    0.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482    1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671    2.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8972    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    0.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153   -0.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7357   -0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9449   -0.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096   -1.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -2.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877   -1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -2.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -3.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314   -3.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576   -1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6272   -2.1032    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  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  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.3718   -2.9182   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2412   -2.5273    0.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9315   -1.1944    0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8361   -0.2902   -0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5368    1.0385   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4181    1.5193    0.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552    0.6001    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463   -0.7266    1.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720   -1.8303    1.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4239   -1.5207    1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.7323    1.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4468   -0.2696    1.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -0.6626    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2762   -1.4817   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6074   -2.0442   -1.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.9135   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4288   -2.7725   -1.0631 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949   -4.1648   -1.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1873    0.1470   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7306    1.5881   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3296    1.7026   -0.8334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009    2.5894    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659    2.4758   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2808    1.4973   -0.9552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499    3.5039    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    3.0000    0.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3197   -2.5899   -0.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4447   -4.0288   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625   -2.4849   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6884   -0.6305   -0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    1.7628   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    0.9623    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.3674    3.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8272    0.3169    2.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0462   -2.6022   -2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -4.5766   -2.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5780   -4.4364   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859   -4.6428   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9991    0.2216    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067   -0.1089   -0.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4197    2.0716   -1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    2.1997    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    0.7313   -1.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    2.1731   -1.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883    2.4460    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    3.6311   -0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5068    4.3005    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    4.0562   -0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6172    3.5720    1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0126    3.4098   -0.1828 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 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 16 14  2  0
 14 15  1  0
  8  3  1  0
  7  6  1  0
 14 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  5 31  1  0
 26 49  1  0
 26 50  1  0
 25 47  1  0
 25 48  1  0
 22 45  1  0
 22 46  1  0
 21 43  1  0
 21 44  1  0
 20 41  1  0
 20 42  1  0
 19 39  1  0
 19 40  1  0
 12 34  1  0
 11 33  1  0
  7 32  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 15 35  1  0
M  END


  Mrv1533004251514592D          

 26 28  0  0  0  0            999 V2000
    1.5321   -3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9031   -2.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044   -1.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -0.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1085    0.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358    0.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482    1.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9671    2.1162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8972    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    0.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153   -0.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7357   -0.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9449   -0.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3096   -1.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -2.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6877   -1.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -2.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556   -3.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1314   -3.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8576   -1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6272   -2.1032    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  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  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  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240999

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CCC(=O)CCCCC3=CC=C(OC1=C2)C(OC)=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/c1-24-17-11-8-14-7-10-16(22)6-4-3-5-15-9-12-18(26-19(17)13-14)21(25-2)20(15)23/h8-9,11-13,23H,3-7,10H2,1-2H3

> <INCHI_KEY>
WQHLZXQHMPOZGL-UHFFFAOYSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.418

> <EXACT_MASS>
356.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.367117047881514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
19-hydroxy-4,18-dimethoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.461367621666666

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.880825691633602

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7154820212681474

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
99.13269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-hydroxy-4,18-dimethoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.860  -6.779   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.581  -5.921   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.686  -4.384   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.381  -3.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.471  -1.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.855  -1.251   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.069   0.319   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.867   1.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.197   2.502   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.672   3.950   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.757   2.715   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.275   2.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.482   1.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.175  -0.226   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.840  -1.804   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.364  -1.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.178  -2.286   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.349  -3.838   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.708  -4.041   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.114  -3.702   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.150  -2.134   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.860  -4.367   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.131  -5.883   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.579  -6.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.067  -3.371   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.504  -3.926   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20    6                                                       
CONECT   22   18   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   15   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₅

Average Mass

356.4180 Da

Monoisotopic Mass

356.16237 Da

IUPAC Name

19-hydroxy-4,18-dimethoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

Traditional Name

19-hydroxy-4,18-dimethoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CCC(=O)CCCCC3=CC=C(OC1=C2)C(OC)=C3O

InChI Identifier

InChI=1S/C21H24O5/c1-24-17-11-8-14-7-10-16(22)6-4-3-5-15-9-12-18(26-19(17)13-14)21(25-2)20(15)23/h8-9,11-13,23H,3-7,10H2,1-2H3

InChI Key

WQHLZXQHMPOZGL-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, 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
Juglans regia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Cyclic diarylheptanoids

Direct Parent

Meta,para-diphenylether diarylheptanoids

Alternative Parents

Substituents

Meta,para-diphenylether diarylheptanoid
Oxyneolignan skeleton
Diaryl ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Cyclic ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:66126 )
aromatic ether (CHEBI:66126 )
phenols (CHEBI:66126 )
methoxybenzene (CHEBI:66126 )

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	4.21	ALOGPS
logP	4.46	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.88	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.13 m³·mol⁻¹	ChemAxon
Polarizability	37.37 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70697839

PDB ID

Not Available

ChEBI ID

66126

Good Scents ID

Not Available

References

General References

Liu J, Meng M, Li C, Huang X, Di D: Simultaneous determination of three diarylheptanoids and an alpha-tetralone derivative in the green walnut husks (Juglans regia L.) by high-performance liquid chromatography with photodiode array detector. J Chromatogr A. 2008 May 9;1190(1-2):80-5. doi: 10.1016/j.chroma.2008.02.083. Epub 2008 Mar 2. [PubMed:18343385 ]
Liu JX, Di DL, Wei XN, Han Y: Cytotoxic diarylheptanoids from the pericarps of walnuts (Juglans regia). Planta Med. 2008 Jun;74(7):754-9. doi: 10.1055/s-2008-1074536. Epub 2008 May 21. [PubMed:18496782 ]
Li C, Liu JX, Zhao L, Di DL, Meng M, Jiang SX: Capillary zone electrophoresis for separation and analysis of four diarylheptanoids and an alpha-tetralone derivative in the green walnut husks (Juglans regia L.). J Pharm Biomed Anal. 2008 Nov 4;48(3):749-53. doi: 10.1016/j.jpba.2008.07.016. Epub 2008 Jul 30. [PubMed:18771874 ]
Yang H, Sung SH, Kim J, Kim YC: Neuroprotective diarylheptanoids from the leaves and twigs of juglans sinensis against glutamate-induced toxicity in HT22 cells. Planta Med. 2011 May;77(8):841-5. doi: 10.1055/s-0030-1250609. Epub 2010 Dec 14. [PubMed:21157684 ]
LOTUS database [Link]

Showing NP-Card for juglanin a (NP0240999)

MOL for NP0240999 (juglanin a)

3D MOL for NP0240999 (juglanin a)

3D SDF for NP0240999 (juglanin a)

3D-SDF for NP0240999 (juglanin a)

PDB for NP0240999 (juglanin a)

3D PDB for NP0240999 (juglanin a)

SMILES for NP0240999 (juglanin a)

INCHI for NP0240999 (juglanin a)

Structure for NP0240999 (juglanin a)

3D Structure for NP0240999 (juglanin a)