NP-MRD: Showing NP-Card for (3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one (NP0268085)

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Record Information

Version

2.0

Created at

2022-09-08 13:05:23 UTC

Updated at

2022-09-08 13:05:23 UTC

NP-MRD ID

NP0268085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one

Description

Calocedrin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one is found in Calocedrus formosana and Pterocarpus santalinus. (3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one was first documented in 2010 (PMID: 20184021). Based on a literature review a small amount of articles have been published on Calocedrin (PMID: 26521861) (PMID: 27041873).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215052D          

 27 31  0  0  1  0            999 V2000
    5.7064    3.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0100    0.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2544    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259   -0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3820   -1.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689   -1.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -1.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128   -0.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4994   -2.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689   -2.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
  6 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -1.8698    1.4897   -1.9667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.3507   -1.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9613   -0.8393   -2.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666   -1.9097   -1.9876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3619   -2.2585   -3.1505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966   -1.3806   -0.9369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7725   -1.5566    0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0347   -0.8266    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -1.3481    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4163   -0.6152    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702    0.6620    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1489    1.2075    1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    0.4656    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650    2.5101    1.7393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6813    2.8873    1.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184    1.6331    1.1929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402    0.0446   -1.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.8675   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2360    0.4711   -0.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -0.5813   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -0.9248   -0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7237   -0.2416    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9715    0.8348    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743    1.1672    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7091    1.3422    2.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    0.8885    2.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8723   -0.3442    1.3492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372   -2.7793   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -3.1956   -3.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8361   -1.9223   -0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0398   -1.1665    1.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8735   -2.6381    0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3684   -2.3317   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4091   -1.0014    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500    0.9341    1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258    3.4887    0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    3.3951    2.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7771    1.9221   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.1797   -1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7918   -1.7703   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1824    2.0060    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4685    0.7045    3.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6922    1.5390    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 27  1  0
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 17  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  2  0
  6  4  1  0
 13  8  1  0
 24 19  1  0
 12 11  1  0
 23 22  1  0
  5 29  1  0
  4 28  1  1
 18 38  1  0
 20 39  1  0
 21 40  1  0
 26 42  1  0
 26 43  1  0
 24 41  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
  9 33  1  0
 10 34  1  0
 15 36  1  0
 15 37  1  0
 13 35  1  0
M  END


  Mrv1652309082215052D          

 27 31  0  0  1  0            999 V2000
    5.7064    3.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0100    0.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2544    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259   -0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2105   -0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3820   -1.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689   -1.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -1.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128   -0.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4994   -2.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7689   -2.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
  6 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1OC(=O)\C(=C\C2=CC=C3OCOC3=C2)[C@H]1CC1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O7/c21-19-13(5-11-1-3-15-17(7-11)25-9-23-15)14(20(22)27-19)6-12-2-4-16-18(8-12)26-10-24-16/h1-5,7-8,14,20,22H,6,9-10H2/b13-5+/t14-,20-/m1/s1

> <INCHI_KEY>
OFNLHWUUBXCFIC-UBOKZLNTSA-N

> <FORMULA>
C20H16O7

> <MOLECULAR_WEIGHT>
368.341

> <EXACT_MASS>
368.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.796777062299356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,4R,5R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(2H-1,3-benzodioxol-5-yl)methylidene]-5-hydroxyoxolan-2-one

> <JCHEM_LOGP>
3.148568980333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.940448601333756

> <JCHEM_PKA_STRONGEST_BASIC>
-4.137047781776615

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
92.24100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,4R,5R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-(2H-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-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  O   UNK     0      10.652   5.746   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.332   4.239   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.362   3.095   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.592   1.761   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.219   0.354   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.086   2.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.941   1.051   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.262  -0.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.726  -0.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.046  -2.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.902  -3.468   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.437  -2.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.117  -1.486   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.532  -4.238   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.437  -5.484   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.902  -5.008   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    6    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₇

Average Mass

368.3410 Da

Monoisotopic Mass

368.08960 Da

IUPAC Name

(3E,4R,5R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(2H-1,3-benzodioxol-5-yl)methylidene]-5-hydroxyoxolan-2-one

Traditional Name

(3E,4R,5R)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-(2H-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1OC(=O)\C(=C\C2=CC=C3OCOC3=C2)[C@H]1CC1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C20H16O7/c21-19-13(5-11-1-3-15-17(7-11)25-9-23-15)14(20(22)27-19)6-12-2-4-16-18(8-12)26-10-24-16/h1-5,7-8,14,20,22H,6,9-10H2/b13-5+/t14-,20-/m1/s1

InChI Key

OFNLHWUUBXCFIC-UBOKZLNTSA-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
Calocedrus formosana	LOTUS Database	35616633
Pterocarpus santalinus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactol
Dibenzylbutyrolactone
Lignan lactone
Benzodioxole
Gamma butyrolactone
Benzenoid
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	3.15	ChemAxon
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.24 m³·mol⁻¹	ChemAxon
Polarizability	34.8 Å³	ChemAxon
Number of Rings	5	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

C00053170

Chemspider ID

8174663

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9999082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jung HJ, Jung HA, Min BS, Choi JS: Anticholinesterase and beta-Site Amyloid Precursor Protein Cleaving Enzyme 1 Inhibitory Compounds from the Heartwood of Juniperus chinensis. Chem Pharm Bull (Tokyo). 2015;63(11):955-60. doi: 10.1248/cpb.c15-00504. [PubMed:26521861 ]
Bulle S, Reddyvari H, Nallanchakravarthula V, Vaddi DR: Therapeutic Potential of Pterocarpus santalinus L.: An Update. Pharmacogn Rev. 2016 Jan-Jun;10(19):43-9. doi: 10.4103/0973-7847.176575. [PubMed:27041873 ]
Chang CI, Chen CR, Chen WC, Kuo CL, Kuo YH: A new phenolic and a new lignan from the roots of Juniperus chinensis. Nat Prod Commun. 2010 Jan;5(1):55-7. [PubMed:20184021 ]
LOTUS database [Link]

Showing NP-Card for (3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one (NP0268085)

MOL for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

3D MOL for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

3D SDF for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

3D-SDF for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

PDB for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

3D PDB for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

SMILES for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

INCHI for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

Structure for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)

3D Structure for NP0268085 ((3e,4r,5r)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-(2h-1,3-benzodioxol-5-ylmethylidene)-5-hydroxyoxolan-2-one)