NP-MRD: Showing NP-Card for (3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one (NP0175298)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 12:43:17 UTC

Updated at

2022-09-03 12:43:17 UTC

NP-MRD ID

NP0175298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one

Description

Guayadequiol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one is found in Bupleurum salicifolium. (3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one was first documented in 2021 (PMID: 34560578). Based on a literature review very few articles have been published on Guayadequiol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214432D          

 28 31  0  0  1  0            999 V2000
    6.5248    6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8574    6.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    5.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2762    4.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3624    3.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1161    3.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023    2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1224    2.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074    1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  2  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
    6.7835    4.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6973    4.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3647    5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    6.1872    0.0000 C   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
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -7.2606   -0.3187   -1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3728    0.1888   -0.3006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108    0.2350   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050   -0.2349   -1.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121   -0.1698   -1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2460    0.3532   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    0.4370   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2174   -0.8663   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6679   -1.9506   -0.9041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -0.8929    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -1.5512    1.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -0.0262    1.8899 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3963    0.1453    1.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.8288    0.0039 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0420   -0.4326   -1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824   -0.4337   -0.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273   -1.5904   -1.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5720   -1.6125   -0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2298   -0.4959   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4827    0.6520   -0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    0.6836   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3725    1.6183    0.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5545    0.9666    0.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435   -0.2522    0.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8975    0.8049    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633    0.7635    0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8869    1.2286    1.7385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0613    1.7559    2.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2395   -0.5016   -0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4766    0.3991   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8705   -1.2702   -1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0057   -0.6385   -2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5167   -0.5317   -2.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5136    0.5333   -1.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276    1.2898   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5999   -1.7708   -1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4149    1.1764    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -0.0386    1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851   -1.8138    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.2104   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    0.5245   -1.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7892   -2.5033   -1.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1694   -2.5121   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5827    1.6010   -0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4918    0.7447    1.9058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4578    1.5794    0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3107    1.2137    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2631    1.0121    3.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7150    1.8029    3.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6399    2.7380    2.4984 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  1  0
  8  9  1  6
  8 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 10  8  1  0
 21 16  1  0
 20 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  7 35  1  0
  9 36  1  0
 14 39  1  1
 15 40  1  0
 15 41  1  0
 17 42  1  0
 18 43  1  0
 23 45  1  0
 23 46  1  0
 21 44  1  0
 13 37  1  0
 13 38  1  0
 25 47  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
M  END


  Mrv1652309032214432D          

 28 31  0  0  1  0            999 V2000
    6.5248    6.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8574    6.0378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9436    5.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2762    4.7324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3624    3.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1161    3.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023    2.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    2.2710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1224    2.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9074    1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  2  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
    6.7835    4.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6973    4.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3647    5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2785    6.1872    0.0000 C   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
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@@]2(O)[C@@H](CC3=CC=C4OCOC4=C3)COC2=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-24-16-5-4-14(9-18(16)25-2)10-21(23)15(11-26-20(21)22)7-13-3-6-17-19(8-13)28-12-27-17/h3-6,8-9,15,23H,7,10-12H2,1-2H3/t15-,21+/m0/s1

> <INCHI_KEY>
XQAPIFWFLMEZDZ-YCRPNKLZSA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.158378234050794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.6603707660000007

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.998707635560741

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11156528020573

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
98.89470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      12.180  12.176   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.934  11.271   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.095   9.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.849   8.834   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.010   7.302   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.417   6.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.578   5.144   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.332   4.239   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.562   5.573   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.362   3.095   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.894   3.256   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.592   1.761   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.086   2.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.663   7.581   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.502   9.113   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.748  10.018   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.587  11.549   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25    6   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

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

Traditional Name

(3R,4S)-4-(2H-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@@]2(O)[C@@H](CC3=CC=C4OCOC4=C3)COC2=O)C=C1OC

InChI Identifier

InChI=1S/C21H22O7/c1-24-16-5-4-14(9-18(16)25-2)10-21(23)15(11-26-20(21)22)7-13-3-6-17-19(8-13)28-12-27-17/h3-6,8-9,15,23H,7,10-12H2,1-2H3/t15-,21+/m0/s1

InChI Key

XQAPIFWFLMEZDZ-YCRPNKLZSA-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
Bupleurum salicifolium	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

Dibenzylbutyrolactone
Lignan lactone
Dimethoxybenzene
O-dimethoxybenzene
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
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	2.75	ALOGPS
logP	2.66	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12	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	6	ChemAxon
Refractivity	98.89 m³·mol⁻¹	ChemAxon
Polarizability	40.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

14630578

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Orcic D, Berezni S, Skoric D, Mimica-Dukic N: Comprehensive study of Anthriscus sylvestris lignans. Phytochemistry. 2021 Dec;192:112958. doi: 10.1016/j.phytochem.2021.112958. Epub 2021 Sep 21. [PubMed:34560578 ]
LOTUS database [Link]

Showing NP-Card for (3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one (NP0175298)

MOL for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

3D MOL for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

3D SDF for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

3D-SDF for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

PDB for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

3D PDB for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

SMILES for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

INCHI for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

Structure for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)

3D Structure for NP0175298 ((3r,4s)-4-(2h-1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]-3-hydroxyoxolan-2-one)