NP-MRD: Showing NP-Card for neglignan B (NP0043444)

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Record Information

Version

1.0

Created at

2021-06-21 00:50:58 UTC

Updated at

2021-06-30 00:19:07 UTC

NP-MRD ID

NP0043444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

neglignan B

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2386330 belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. neglignan B is found in Schisandra neglecta. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on CHEMBL2386330 (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451) (PMID: 26389436).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102503D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102503D          

 58 61  0  0  0  0            999 V2000
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   -2.8501   -0.6938   -0.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1165    0.0144   -2.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.2730    0.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3377    1.4822    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    0.7674    0.0708 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1726   -2.0319    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5343   -3.0513    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -3.8116    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -1.5541    4.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780    2.6653    3.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -5.1436   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -4.1931   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456   -4.6941    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6749   -2.3065   -3.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -0.5918   -2.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7713   -1.1061   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -2.2432   -2.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080   -2.2786   -6.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.5916   -6.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -2.3555   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -3.1916   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387   -1.0610   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    0.5493   -2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9304    0.7406   -2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.7009   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -0.2908    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.1808   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850    1.1638    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    2.0349    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.7609    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303    0.9359   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0  0  0  0
 26 27  1  0  0  0  0
 12  3  2  0  0  0  0
 28 29  1  0  0  0  0
 30 31  1  0  0  0  0
 19 18  1  0  0  0  0
  3  4  1  0  0  0  0
 16 17  1  0  0  0  0
  4  6  2  0  0  0  0
 17 18  2  0  0  0  0
  6 10  1  0  0  0  0
 18 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 19  1  0  0  0  0
 10 11  2  0  0  0  0
 20 21  1  0  0  0  0
 20 15  1  0  0  0  0
 21 22  1  0  0  0  0
 16 26  1  0  0  0  0
 12 13  1  0  0  0  0
 15 11  1  0  0  0  0
 13 14  1  0  0  0  0
 10 32  1  0  0  0  0
  3  2  1  0  0  0  0
 19 20  2  0  0  0  0
  4  5  1  0  0  0  0
 26 28  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
  7  8  2  0  0  0  0
 28 30  1  0  0  0  0
  7  9  1  0  0  0  0
 30 32  1  0  0  0  0
  2  1  1  0  0  0  0
 17 41  1  0  0  0  0
 26 47  1  1  0  0  0
 32 57  1  0  0  0  0
 32 58  1  0  0  0  0
 28 49  1  1  0  0  0
 30 53  1  1  0  0  0
 27 48  1  0  0  0  0
 29 50  1  0  0  0  0
 29 51  1  0  0  0  0
 29 52  1  0  0  0  0
 31 54  1  0  0  0  0
 31 55  1  0  0  0  0
 31 56  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
 22 42  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
  5 36  1  0  0  0  0
  9 37  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C2=C1C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C1=C2C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O9/c1-9-6-11-14(21(29-4)22(30-5)18(25)16(11)23(26)27)15-12(17(24)10(9)2)7-13-19(20(15)28-3)32-8-31-13/h7,9-10,17,24-25H,6,8H2,1-5H3,(H,26,27)/t9-,10-,17-/m1/s1

> <INCHI_KEY>
CYOQLUBFWYSAMW-VHCOLVSPSA-N

> <FORMULA>
C23H26O9

> <MOLECULAR_WEIGHT>
446.452

> <EXACT_MASS>
446.157682417

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.19895150804412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,10R,11R)-5,11-dihydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaene-6-carboxylic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
3.6481434966666653

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.957359713096022

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.813410884838911

> <JCHEM_PKA_STRONGEST_BASIC>
-3.134483745053438

> <JCHEM_POLAR_SURFACE_AREA>
123.91000000000003

> <JCHEM_REFRACTIVITY>
113.60570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10R,11R)-5,11-dihydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    3.8417   -2.9123    2.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -2.7582    2.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7223   -1.9526    2.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -0.9348    2.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.8201    4.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.0527    2.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599    0.9919    2.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.9673    3.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    2.0476    3.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -0.1731    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6772   -1.2142    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -2.1239    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720   -3.1797    0.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693   -4.3537    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -1.3658   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -1.7757   -1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7564   -1.9805   -3.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624   -1.7419   -4.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -1.3152   -3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -1.1262   -2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044   -0.6464   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228   -1.1840   -2.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -1.1040   -4.5341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7775   -1.4581   -5.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -1.8684   -5.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -1.9617   -1.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7438   -3.0011   -1.7379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.6938   -0.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1165    0.0144   -2.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.2730    0.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3377    1.4822    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    0.7674    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -2.0319    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5343   -3.0513    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -3.8116    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -1.5541    4.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780    2.6653    3.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -5.1436   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -4.1931   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456   -4.6941    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6749   -2.3065   -3.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -0.5918   -2.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7713   -1.1061   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -2.2432   -2.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080   -2.2786   -6.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.5916   -6.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -2.3555   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -3.1916   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387   -1.0610   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    0.5493   -2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9304    0.7406   -2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.7009   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -0.2908    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.1808   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850    1.1638    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    2.0349    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.7609    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303    0.9359   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 26 27  1  0
 12  3  2  0
 28 29  1  0
 30 31  1  0
 19 18  1  0
  3  4  1  0
 16 17  1  0
  4  6  2  0
 17 18  2  0
  6 10  1  0
 18 25  1  0
 25 24  1  0
 24 23  1  0
 23 19  1  0
 10 11  2  0
 20 21  1  0
 20 15  1  0
 21 22  1  0
 16 26  1  0
 12 13  1  0
 15 11  1  0
 13 14  1  0
 10 32  1  0
  3  2  1  0
 19 20  2  0
  4  5  1  0
 26 28  1  0
  6  7  1  0
 11 12  1  0
  7  8  2  0
 28 30  1  0
  7  9  1  0
 30 32  1  0
  2  1  1  0
 17 41  1  0
 26 47  1  1
 32 57  1  0
 32 58  1  0
 28 49  1  1
 30 53  1  1
 27 48  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 24 45  1  0
 24 46  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
  5 36  1  0
  9 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.842  -2.912   2.406  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.531  -2.758   2.954  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.722  -1.953   2.189  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.061  -0.935   2.871  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.242  -0.820   4.226  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.225  -0.053   2.185  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.460   0.992   2.961  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.613   0.967   3.344  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.352   2.048   3.144  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.018  -0.173   0.789  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.677  -1.214   0.090  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.489  -2.124   0.819  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.072  -3.180   0.153  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.269  -4.354   0.294  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.540  -1.366  -1.379  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.696  -1.776  -1.967  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.756  -1.980  -3.363  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.362  -1.742  -4.129  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.545  -1.315  -3.579  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.669  -1.126  -2.212  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.804  -0.646  -1.607  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.023  -1.184  -2.110  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.494  -1.104  -4.534  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.778  -1.458  -5.732  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.422  -1.868  -5.482  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.958  -1.962  -1.134  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.744  -3.001  -1.738  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.850  -0.694  -0.982  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.116   0.014  -2.321  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.397   0.273   0.155  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.338   1.482   0.276  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.936   0.767   0.071  0.00  0.00           C+0
HETATM   33  H   UNK     0       4.173  -2.032   1.843  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.534  -3.051   3.242  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.890  -3.812   1.785  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.837  -1.554   4.477  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.178   2.665   3.688  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.726  -5.144  -0.309  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.251  -4.193  -0.075  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.246  -4.694   1.335  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.675  -2.307  -3.843  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.380  -0.592  -2.957  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.771  -1.106  -1.315  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.934  -2.243  -2.377  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.308  -2.279  -6.228  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.766  -0.592  -6.403  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.698  -2.356  -0.145  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.479  -3.192  -1.131  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.839  -1.061  -0.665  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.234   0.549  -2.684  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.930   0.741  -2.229  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.431  -0.701  -3.087  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.522  -0.291   1.091  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.209   2.181  -0.557  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.385   1.164   0.305  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.138   2.035   1.200  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.840   1.761   0.528  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.630   0.936  -0.967  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1                                                       
CONECT    3   12    4    2                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   36                                                       
CONECT    6    4   10    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   37                                                       
CONECT   10    6   11   32                                                  
CONECT   11   10   15   12                                                  
CONECT   12    3   13   11                                                  
CONECT   13   12   14                                                       
CONECT   14   13   38   39   40                                             
CONECT   15   16   20   11                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   41                                                  
CONECT   18   19   17   25                                                  
CONECT   19   18   23   20                                                  
CONECT   20   21   15   19                                                  
CONECT   21   20   22                                                       
CONECT   22   21   42   43   44                                             
CONECT   23   24   19                                                       
CONECT   24   25   23   45   46                                             
CONECT   25   18   24                                                       
CONECT   26   27   16   28   47                                             
CONECT   27   26   48                                                       
CONECT   28   29   26   30   49                                             
CONECT   29   28   50   51   52                                             
CONECT   30   31   28   32   53                                             
CONECT   31   30   54   55   56                                             
CONECT   32   10   30   57   58                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    9                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   17                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   22                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
CONECT   47   26                                                            
CONECT   48   27                                                            
CONECT   49   28                                                            
CONECT   50   29                                                            
CONECT   51   29                                                            
CONECT   52   29                                                            
CONECT   53   30                                                            
CONECT   54   31                                                            
CONECT   55   31                                                            
CONECT   56   31                                                            
CONECT   57   32                                                            
CONECT   58   32                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
    3.8417   -2.9123    2.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -2.7582    2.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7223   -1.9526    2.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607   -0.9348    2.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420   -0.8201    4.2263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245   -0.0527    2.1854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599    0.9919    2.9605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.9673    3.3435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3515    2.0476    3.1441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0183   -0.1731    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6772   -1.2142    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -2.1239    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0720   -3.1797    0.1534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2693   -4.3537    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -1.3658   -1.3795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -1.7757   -1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7564   -1.9805   -3.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624   -1.7419   -4.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -1.3152   -3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693   -1.1262   -2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044   -0.6464   -1.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0228   -1.1840   -2.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4938   -1.1040   -4.5341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7775   -1.4581   -5.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218   -1.8684   -5.4822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -1.9617   -1.1336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7438   -3.0011   -1.7379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.6938   -0.9820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1165    0.0144   -2.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.2730    0.1552 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3377    1.4822    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    0.7674    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -2.0319    1.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5343   -3.0513    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896   -3.8116    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -1.5541    4.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780    2.6653    3.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7264   -5.1436   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508   -4.1931   -0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2456   -4.6941    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6749   -2.3065   -3.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -0.5918   -2.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7713   -1.1061   -1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -2.2432   -2.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080   -2.2786   -6.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7655   -0.5916   -6.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -2.3555   -0.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4789   -3.1916   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8387   -1.0610   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    0.5493   -2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9304    0.7406   -2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4309   -0.7009   -3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -0.2908    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.1808   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3850    1.1638    0.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    2.0349    1.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.7609    0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303    0.9359   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 26 27  1  0
 12  3  2  0
 28 29  1  0
 30 31  1  0
 19 18  1  0
  3  4  1  0
 16 17  1  0
  4  6  2  0
 17 18  2  0
  6 10  1  0
 18 25  1  0
 25 24  1  0
 24 23  1  0
 23 19  1  0
 10 11  2  0
 20 21  1  0
 20 15  1  0
 21 22  1  0
 16 26  1  0
 12 13  1  0
 15 11  1  0
 13 14  1  0
 10 32  1  0
  3  2  1  0
 19 20  2  0
  4  5  1  0
 26 28  1  0
  6  7  1  0
 11 12  1  0
  7  8  2  0
 28 30  1  0
  7  9  1  0
 30 32  1  0
  2  1  1  0
 17 41  1  0
 26 47  1  1
 32 57  1  0
 32 58  1  0
 28 49  1  1
 30 53  1  1
 27 48  1  0
 29 50  1  0
 29 51  1  0
 29 52  1  0
 31 54  1  0
 31 55  1  0
 31 56  1  0
 24 45  1  0
 24 46  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
  5 36  1  0
  9 37  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₉

Average Mass

446.4520 Da

Monoisotopic Mass

446.15768 Da

IUPAC Name

(9R,10R,11R)-5,11-dihydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaene-6-carboxylic acid

Traditional Name

(9R,10R,11R)-5,11-dihydroxy-3,4,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C2=C1C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C1=C2C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H]

InChI Identifier

InChI=1S/C23H26O9/c1-9-6-11-14(21(29-4)22(30-5)18(25)16(11)23(26)27)15-12(17(24)10(9)2)7-13-19(20(15)28-3)32-8-31-13/h7,9-10,17,24-25H,6,8H2,1-5H3,(H,26,27)/t9-,10-,17-/m1/s1

InChI Key

CYOQLUBFWYSAMW-VHCOLVSPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Schisandra neglecta	JEOL database	Gao, X. -M., et al, J. Nat. Prod. 76, 1052 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Dibenzocyclooctane lignan
M-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Salicylic acid or derivatives
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Vinylogous acid
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.11	ALOGPS
logP	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.61 m³·mol⁻¹	ChemAxon
Polarizability	45.2 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

Not Available

Chemspider ID

30825791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71726087

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Authors unspecified: Cancer Pain (PDQ(R)): Health Professional Version. 2002. [PubMed:26389387 ]
Authors unspecified: Ovarian, Fallopian Tube, and Primary Peritoneal Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389336 ]
Authors unspecified: Informal Caregivers in Cancer: Roles, Burden, and Support (PDQ(R)): Health Professional Version. 2002. [PubMed:26389284 ]
Authors unspecified: Neuroblastoma Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389278 ]
Authors unspecified: Late Effects of Treatment for Childhood Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389273 ]
Authors unspecified: Lip and Oral Cavity Cancer Treatment (Adult) (PDQ(R)): Health Professional Version. 2002. [PubMed:26389262 ]
Gao, X. -M., et al. (2013). Gao, X. -M., et al, J. Nat. Prod. 76, 1052 (2013). J. Nat. Prod..

Showing NP-Card for neglignan B (NP0043444)

MOL for NP0043444 (neglignan B)

3D MOL for NP0043444 (neglignan B)

3D SDF for NP0043444 (neglignan B)

3D-SDF for NP0043444 (neglignan B)

PDB for NP0043444 (neglignan B)

3D PDB for NP0043444 (neglignan B)

SMILES for NP0043444 (neglignan B)

INCHI for NP0043444 (neglignan B)

Structure for NP0043444 (neglignan B)

3D Structure for NP0043444 (neglignan B)