NP-MRD: Showing NP-Card for Smiglaside B (NP0075784)

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Record Information

Version

2.0

Created at

2022-04-28 21:01:00 UTC

Updated at

2022-04-28 21:01:00 UTC

NP-MRD ID

NP0075784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Smiglaside B

Description

Simiglaside B belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Smiglaside B is found in Smilax glabra . Based on a literature review very few articles have been published on Simiglaside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223012D          

 68 72  0  0  1  0            999 V2000
   -1.6242   -5.0437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4492   -5.0437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7041   -4.2590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367   -3.7741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3693   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317   -3.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8068   -3.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -2.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8217   -1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232   -2.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -1.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -1.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -0.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831   -0.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -1.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -2.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731   -2.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280   -1.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881   -0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1130   -0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -3.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667   -3.0467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6717   -2.3280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4966   -2.3193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9166   -3.0294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5116   -3.7482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6866   -3.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9315   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7565   -4.4497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1764   -5.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7714   -5.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0014   -5.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7415   -3.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9016   -1.6006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517   -1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567   -0.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4816   -0.8905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367   -0.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888   -4.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1019   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865   -4.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9303   -5.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5434   -5.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719   -6.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -6.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -7.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0288   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8135   -8.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9850   -7.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8573   -9.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -8.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -8.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -5.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188   -5.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1661   -6.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1694   -7.0460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866   -6.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715   -6.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920   -6.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6276   -6.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480   -5.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -6.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974   -7.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7769   -7.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823   -8.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -8.7896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7534   -6.5286    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  6  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 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
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 25 33  1  1  0  0  0
 24 34  1  6  0  0  0
 23 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  3 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
 47 50  1  0  0  0  0
 46 51  1  0  0  0  0
 51 52  1  0  0  0  0
  2 53  1  1  0  0  0
  1 54  1  6  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 56 58  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 60 65  1  0  0  0  0
 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 63 68  1  0  0  0  0
M  END

     RDKit          3D

118122  0  0  0  0  0  0  0  0999 V2000
   -1.2114    7.9959   -2.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353    8.0811   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995    7.3504    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0206    6.3620   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099    5.6365    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576    4.5431    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    4.1325   -0.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8234    3.0581   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977    2.8449   -1.8597 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4342    2.2339    0.2994 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2627    1.1518   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -0.1571   -0.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.9103   -2.8462   -3.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2723   -3.6748   -6.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2439   -3.4937   -7.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5643   -4.6495   -5.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0740   -2.7979   -9.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650    0.6655   -6.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3172   -0.6493   -5.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836   -2.7974    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223012D          

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 63 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](COC(=O)\C=C\C3=CC(OC)=C(O)C=C3)(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3OC(C)=O)[C@@H](OC(=O)\C=C\C3=CC(OC)=C(O)C=C3)[C@@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C46H50O22/c1-24(47)61-21-35-40(55)42(57)43(64-25(2)48)45(65-35)68-46(23-63-38(53)16-10-27-7-13-30(50)33(19-27)59-4)44(66-39(54)17-11-28-8-14-31(51)34(20-28)60-5)41(56)36(67-46)22-62-37(52)15-9-26-6-12-29(49)32(18-26)58-3/h6-20,35-36,40-45,49-51,55-57H,21-23H2,1-5H3/b15-9+,16-10+,17-11+/t35-,36-,40-,41-,42+,43-,44+,45-,46+/m1/s1

> <INCHI_KEY>
JRGWEHCLTJUJTI-AWJIXBOWSA-N

> <FORMULA>
C46H50O22

> <MOLECULAR_WEIGHT>
954.884

> <EXACT_MASS>
954.27937325

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
95.13492259337968

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3S,4R,5R)-2-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-6-[(acetyloxy)methyl]-4,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
4.071378249

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.867086180796534

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.390300825819363

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6498095943046263

> <JCHEM_POLAR_SURFACE_AREA>
308.26

> <JCHEM_REFRACTIVITY>
231.11249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4R,5R)-2-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-6-[(acetyloxy)methyl]-4,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -3.032  -9.415   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.572  -9.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.048  -7.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.802  -7.045   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.556  -7.950   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.046  -5.703   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.506  -5.687   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.750  -4.346   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.534  -3.020   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.790  -4.329   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.546  -2.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.086  -2.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.842  -1.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.382  -1.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.166  -2.939   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.410  -4.281   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.870  -4.297   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.706  -2.923   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.138  -0.272   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.678  -0.256   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.558  -5.703   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.098  -5.687   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.854  -4.346   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.394  -4.329   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.178  -5.655   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.422  -6.997   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.882  -7.013   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.206  -8.322   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.745  -8.306   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.529  -9.632   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.773 -10.973   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -13.069  -9.615   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.718  -5.639   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.150  -2.988   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.070  -3.020   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.826  -1.678   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -8.366  -1.662   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.042  -0.353   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.512  -7.474   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -7.657  -8.505   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -9.121  -8.981   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -7.337 -10.011   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -8.481 -11.042   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -8.161 -12.548   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.696 -13.024   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -6.376 -14.530   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -7.521 -15.561   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -8.985 -15.085   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -9.305 -13.578   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -7.200 -17.067   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -4.911 -15.006   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -4.591 -16.512   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -5.477 -10.661   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -2.127 -10.661   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -0.595 -10.500   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       0.310 -11.746   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -0.316 -13.152   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       1.842 -11.585   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       2.747 -12.831   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.278 -12.670   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.905 -11.263   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       6.436 -11.102   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       7.342 -12.348   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       6.715 -13.754   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       5.184 -13.915   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       7.620 -15.000   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       6.994 -16.407   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       8.873 -12.187   0.000  0.00  0.00           O+0
CONECT    1    2    5   54                                                  
CONECT    2    1    3   53                                                  
CONECT    3    2    4   39                                                  
CONECT    4    3    5    6   21                                             
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19                                                            
CONECT   21    4   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   25   34                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   25                                                            
CONECT   34   24                                                            
CONECT   35   23   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39    3   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46   48   50                                                  
CONECT   48   47   49                                                       
CONECT   49   48   44                                                       
CONECT   50   47                                                            
CONECT   51   46   52                                                       
CONECT   52   51                                                            
CONECT   53    2                                                            
CONECT   54    1   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   68                                                  
CONECT   64   63   65   66                                                  
CONECT   65   64   60                                                       
CONECT   66   64   67                                                       
CONECT   67   66                                                            
CONECT   68   63                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₅₀O₂₂

Average Mass

954.8840 Da

Monoisotopic Mass

954.27937 Da

IUPAC Name

[(2S,3S,4R,5R)-2-{[(2R,3R,4S,5S,6R)-3-(acetyloxy)-6-[(acetyloxy)methyl]-4,5-dihydroxyoxan-2-yl]oxy}-4-hydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-5-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxolan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@](COC(=O)\C=C\C3=CC(OC)=C(O)C=C3)(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3OC(C)=O)[C@@H](OC(=O)\C=C\C3=CC(OC)=C(O)C=C3)[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C46H50O22/c1-24(47)61-21-35-40(55)42(57)43(64-25(2)48)45(65-35)68-46(23-63-38(53)16-10-27-7-13-30(50)33(19-27)59-4)44(66-39(54)17-11-28-8-14-31(51)34(20-28)60-5)41(56)36(67-46)22-62-37(52)15-9-26-6-12-29(49)32(18-26)58-3/h6-20,35-36,40-45,49-51,55-57H,21-23H2,1-5H3/b15-9+,16-10+,17-11+/t35-,36-,40-,41-,42+,43-,44+,45-,46+/m1/s1

InChI Key

JRGWEHCLTJUJTI-AWJIXBOWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Smilax glabra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Disaccharide
Methoxyphenol
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
Styrene
1-hydroxy-2-unsubstituted benzenoid
Ketal
Alkyl aryl ether
Phenol
Fatty acid ester
Monocyclic benzene moiety
Oxane
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.4	ALOGPS
logP	4.07	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	308.26 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	231.11 m³·mol⁻¹	ChemAxon
Polarizability	95.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

9832787

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11658052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Smiglaside B (NP0075784)

MOL for NP0075784 (Smiglaside B)

3D MOL for NP0075784 (Smiglaside B)

3D SDF for NP0075784 (Smiglaside B)

3D-SDF for NP0075784 (Smiglaside B)

PDB for NP0075784 (Smiglaside B)

3D PDB for NP0075784 (Smiglaside B)

SMILES for NP0075784 (Smiglaside B)

INCHI for NP0075784 (Smiglaside B)

Structure for NP0075784 (Smiglaside B)

3D Structure for NP0075784 (Smiglaside B)