NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate (NP0191145)

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Record Information

Version

2.0

Created at

2022-09-04 07:59:40 UTC

Updated at

2022-09-04 07:59:40 UTC

NP-MRD ID

NP0191145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate

Description

(3,4,5-Trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]Pentadecan]-8'(14')-ene-12'-carboxylate belongs to the class of organic compounds known as iridoid o-glycosides. (3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate is found in Daphniphyllum macropodum. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton (3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]Pentadecan]-8'(14')-ene-12'-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522102D          

 53 60  0  0  0  0            999 V2000
    1.0851   -2.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -2.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6372   -1.8463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0127   -1.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4973   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975   -0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6130   -0.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -1.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4281    0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8852    0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2841   -0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4241   -0.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7761   -2.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3666   -0.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1885   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0024   -2.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 10 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 33 43  1  0  0  0  0
 37 43  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 31 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 29 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END

     RDKit          3D

108115  0  0  0  0  0  0  0  0999 V2000
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 41 93  1  6
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 34 84  1  0
 34 85  1  0
 42 94  1  6
 43 95  1  0
 44 96  1  1
 45 97  1  0
 46 98  1  1
 47 99  1  0
M  END


  Mrv1533004161522102D          

 53 60  0  0  0  0            999 V2000
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    3.3027   -2.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5980   -2.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0714   -1.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -1.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3666   -0.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1885   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5369   -1.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8322   -1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8063    0.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1839    0.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7173    0.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1166   -3.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464   -3.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729   -3.6813    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 10 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 33 43  1  0  0  0  0
 37 43  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 31 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 29 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(O)CCC2(CO1)C1CN(C)CC22CC(C3CCC(CC1)=C23)C(=O)OCC1OC(OC2OC=C(C3CC=C(CO)C23)C(=O)OC)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H55NO13/c1-4-39(47)12-11-37(19-51-39)22-8-5-20-6-10-24-25(13-38(37,29(20)24)18-40(2)14-22)34(46)49-17-27-30(42)31(43)32(44)36(52-27)53-35-28-21(15-41)7-9-23(28)26(16-50-35)33(45)48-3/h7,16,22-25,27-28,30-32,35-36,41-44,47H,4-6,8-15,17-19H2,1-3H3

> <INCHI_KEY>
XJMWBKAGSQILNJ-UHFFFAOYSA-N

> <FORMULA>
C39H55NO13

> <MOLECULAR_WEIGHT>
745.863

> <EXACT_MASS>
745.367340835

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
78.67068818688101

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
0.2768001716735627

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.419601985313705

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.842711936135379

> <JCHEM_PKA_STRONGEST_BASIC>
10.078735790976907

> <JCHEM_POLAR_SURFACE_AREA>
193.90999999999997

> <JCHEM_REFRACTIVITY>
188.40120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.026  -5.422   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.377  -4.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.413  -3.144   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.923  -3.446   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.890  -3.376   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.928  -2.173   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.489  -0.739   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.011  -0.507   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.993  -1.926   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.799   0.544   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.971   1.649   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.519   1.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.350   0.088   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.674  -1.359   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.764  -2.449   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.130  -1.673   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.868  -0.141   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.981  -3.811   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.452  -3.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.138  -1.971   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.579  -2.581   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -0.792  -1.734   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -2.172  -2.416   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.634  -0.159   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.631  -5.206   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.747  -6.468   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.165  -5.341   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.049  -4.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.583  -4.215   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.467  -2.954   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.001  -3.088   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.884  -1.827   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.418  -1.962   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.069  -3.358   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.603  -3.492   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.487  -2.231   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.836  -0.835   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.439   0.582   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.277   1.593   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.956   0.800   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.539   1.402   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      11.309   0.476   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      14.302  -0.701   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.021  -2.366   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      18.671  -3.762   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      18.905  -1.105   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      20.439  -1.239   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.651  -4.484   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      13.185  -4.619   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      10.767  -5.745   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      11.418  -7.141   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       9.233  -5.611   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       8.350  -6.872   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10   20                                             
CONECT    8    7    9                                                       
CONECT    9    8    3                                                       
CONECT   10    7   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   15   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19    7   14   21                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   10                                                       
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   52                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   48                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   43                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   44                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   33   37                                                  
CONECT   44   36   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   31   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   29   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  120    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1,.0,]pentadecan]-8'(14')-ene-12'-carboxylic acid	Generator
(3,4,5-Trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4ah,5H,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylic acid	Generator

Chemical Formula

C₃₉H₅₅NO₁₃

Average Mass

745.8630 Da

Monoisotopic Mass

745.36734 Da

IUPAC Name

(3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC1(O)CCC2(CO1)C1CN(C)CC22CC(C3CCC(CC1)=C23)C(=O)OCC1OC(OC2OC=C(C3CC=C(CO)C23)C(=O)OC)C(O)C(O)C1O

InChI Identifier

InChI=1S/C39H55NO13/c1-4-39(47)12-11-37(19-51-39)22-8-5-20-6-10-24-25(13-38(37,29(20)24)18-40(2)14-22)34(46)49-17-27-30(42)31(43)32(44)36(52-27)53-35-28-21(15-41)7-9-23(28)26(16-50-35)33(45)48-3/h7,16,22-25,27-28,30-32,35-36,41-44,47H,4-6,8-15,17-19H2,1-3H3

InChI Key

XJMWBKAGSQILNJ-UHFFFAOYSA-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
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Saccharolipid
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Azaspirodecane
Monoterpenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Piperidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Vinylogous ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Amino acid or derivatives
Carboxylic acid ester
Hemiacetal
Azacycle
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Primary alcohol
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.43	ALOGPS
logP	0.28	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	193.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	188.4 m³·mol⁻¹	ChemAxon
Polarizability	78.67 Å³	ChemAxon
Number of Rings	8	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

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

73698830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate (NP0191145)

MOL for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D MOL for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D SDF for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D-SDF for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

PDB for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D PDB for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

SMILES for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

INCHI for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

Structure for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)

3D Structure for NP0191145 ((3,4,5-trihydroxy-6-{[7-(hydroxymethyl)-4-(methoxycarbonyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}oxan-2-yl)methyl 6-ethyl-6-hydroxy-3'-methyl-3'-azaspiro[oxane-3,15'-tetracyclo[6.5.1.1¹,⁵.0¹¹,¹⁴]pentadecan]-8'(14')-ene-12'-carboxylate)