NP-MRD: Showing NP-Card for (2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0237044)

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Record Information

Version

2.0

Created at

2022-09-06 20:05:18 UTC

Updated at

2022-09-06 20:05:18 UTC

NP-MRD ID

NP0237044

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one

Description

Cleomiscosin B belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin. (2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one is found in Brucea javanica and Diatenopteryx sorbifolia. (2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one was first documented in 2007 (PMID: 17802880). Based on a literature review a significant number of articles have been published on Cleomiscosin B (PMID: 24199564) (PMID: 20120038) (PMID: 19720117) (PMID: 18841773) (PMID: 18800331) (PMID: 18651599).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222052D          

 28 31  0  0  1  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    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
  6  5  1  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  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
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
    4.7835   -1.0117   -0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929   -1.6459   -1.1831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305   -2.0007   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0798   -1.7318   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7527   -2.0618   -0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -1.7840    0.9362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3303   -1.2196    0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806    0.1284    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368    1.0028    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332    2.3738    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    3.1733    1.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491    4.5546    1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7353    2.8426   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6130    1.9796   -0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6220    2.4342   -1.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    1.4971   -2.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639    0.1381   -2.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0070   -0.7128   -2.6112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2876   -0.2169   -1.2684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796    0.6045   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611    0.4862    1.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3881   -0.8719    1.9900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5289   -1.0193    3.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1061   -0.2271    4.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -2.6816   -1.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -2.9642   -2.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4459   -2.6199   -2.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.9029   -3.4541 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833   -0.9432   -0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923    0.0071    0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5374   -1.6841    0.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5287   -1.2410    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4834   -2.7493    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2308    4.9893    2.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138    4.9666    0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2865    4.9366    1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    3.9007   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7455    3.4921   -1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2454    1.7937   -2.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996   -1.1209    2.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -0.7380    2.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623   -2.0960    3.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8992   -0.0166    4.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529   -2.9606   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179   -3.4515   -3.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441   -2.6281   -3.3655 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 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 20  2  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 10  1  0
 10 11  1  0
 11 12  1  0
 10  9  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 27  3  1  0
 22  6  1  0
  9  8  1  0
 14 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
 25 44  1  0
 26 45  1  0
 28 46  1  0
  6 33  1  1
 16 39  1  0
 15 38  1  0
 13 37  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 22 40  1  1
 23 41  1  0
 23 42  1  0
 24 43  1  0
M  END


  Mrv1652309062222052D          

 28 31  0  0  1  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    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
  6  5  1  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  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
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  8 20  2  0  0  0  0
 14 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@@H]1OC2=C3OC(=O)C=CC3=CC(OC)=C2O[C@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-19-14(25-2)8-11-4-6-16(23)27-18(11)20(19)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m0/s1

> <INCHI_KEY>
XGADTAYOFHOFIW-RDJZCZTQSA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.356

> <EXACT_MASS>
386.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.79417932612934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_LOGP>
1.8314895329999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.56174869585692

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.908128874944044

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904953549332536

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
97.6586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      12.114   6.105   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.344   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.804   7.438   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    8   14                                                  
CONECT   21    9   22                                                       
CONECT   22   21    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    3   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

C₂₀H₁₈O₈

Average Mass

386.3560 Da

Monoisotopic Mass

386.10017 Da

IUPAC Name

(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

Traditional Name

(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@@H]1OC2=C3OC(=O)C=CC3=CC(OC)=C2O[C@H]1CO

InChI Identifier

InChI=1S/C20H18O8/c1-24-13-7-10(3-5-12(13)22)17-15(9-21)26-19-14(25-2)8-11-4-6-16(23)27-18(11)20(19)28-17/h3-8,15,17,21-22H,9H2,1-2H3/t15-,17-/m0/s1

InChI Key

XGADTAYOFHOFIW-RDJZCZTQSA-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
Brucea javanica	LOTUS Database	35616633
Diatenopteryx sorbifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Coumarinolignans

Sub Class

Not Available

Direct Parent

Coumarinolignans

Alternative Parents

Substituents

Angular-fused coumarolignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
P-dioxolo[2,3-h]coumarin
Coumarin
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Methoxyphenol
1-benzopyran
Anisole
Methoxybenzene
Phenol ether
Phenoxy compound
Pyranone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Pyran
Para-dioxin
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Primary alcohol
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	1.83	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.66 m³·mol⁻¹	ChemAxon
Polarizability	38.79 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019820

Chemspider ID

10155023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11982428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen H, Bai J, Fang ZF, Ma SG, Yu SS, Chen XG: [Chemical constituents from stems of Brucea mollis and their cytotoxic activity]. Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(14):2321-4. [PubMed:24199564 ]
Kaur R, Kumar S, Chatterjee A, Chattopadhyay SK: High-performance liquid chromatographic method for identification and quantification of three potent liver protective coumarinolignoids-cleomiscosin A, cleomiscosin B and cleomiscosin C-in extracts of Cleome viscosa. Biomed Chromatogr. 2010 Sep;24(9):1000-5. doi: 10.1002/bmc.1399. [PubMed:20120038 ]
Begum S, Saxena B, Goyal M, Ranjan R, Joshi VB, Rao ChV, Krishnamurthy S, Sahai M: Study of anti-inflammatory, analgesic and antipyretic activities of seeds of Hyoscyamus niger and isolation of a new coumarinolignan. Fitoterapia. 2010 Apr;81(3):178-84. doi: 10.1016/j.fitote.2009.08.024. Epub 2009 Aug 29. [PubMed:19720117 ]
Lin S, Liu MT, Wang SJ, Li S, Yang YC, Shi JG: [Coumarins from branch of Fraxinus sieboldiana and their antioxidative activity]. Zhongguo Zhong Yao Za Zhi. 2008 Jul;33(14):1708-10. [PubMed:18841773 ]
Chattopadhyay SK, Kumar S, Kaur R, Tandon S, Rane S: Identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in the seeds of Cleome viscosa using liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2009 Apr;23(4):340-56. doi: 10.1002/bmc.1121. [PubMed:18800331 ]
Chattopadhyay SK, Kumar S, Tripathi S, Kaur R, Tandon S, Rane S: High-performance liquid chromatography and LC-ESI-MS method for the identification and quantification of two biologically active isomeric coumarinolignoids cleomiscosin A and cleomiscosin B in different extracts of Cleome viscosa. Biomed Chromatogr. 2008 Dec;22(12):1325-45. doi: 10.1002/bmc.1062. [PubMed:18651599 ]
Xu JF, Feng ZM, Liu J, Zhang PC: New hepatoprotective coumarinolignoids from Mallotus apelta. Chem Biodivers. 2008 Apr;5(4):591-7. doi: 10.1002/cbdv.200890055. [PubMed:18421750 ]
Ma M, Shang XY, Wang SJ, Li S, Yang YC, Shi JG: [Chemical constituents from branch of Macaranga adenantha and their TNF-alpha inhibitory activity]. Zhongguo Zhong Yao Za Zhi. 2007 Jun;32(12):1175-9. [PubMed:17802880 ]
Chattopadhyay SK, Kumar S, Tripathi S, Gupta AK: High-performance liquid chromatographic method for identification and quantification of two isomeric coumarinolignoids-cleomiscosin A and cleomiscosin B-in extracts of Cleome viscosa. Biomed Chromatogr. 2007 Nov;21(11):1214-20. doi: 10.1002/bmc.879. [PubMed:17604358 ]
Liu J, Feng Z, Xu J, Wang Y, Zhang P: Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia. Phytochemistry. 2007 Jul;68(13):1775-80. doi: 10.1016/j.phytochem.2007.05.001. Epub 2007 Jun 13. [PubMed:17570448 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0237044)

MOL for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D MOL for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D SDF for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D-SDF for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

PDB for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D PDB for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

SMILES for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

INCHI for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

Structure for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D Structure for NP0237044 ((2s,3s)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)