NP-MRD: Showing NP-Card for (3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0185480)

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Record Information

Version

1.0

Created at

2022-09-04 00:54:10 UTC

Updated at

2022-09-04 00:54:10 UTC

NP-MRD ID

NP0185480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Phlomoidoside 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. (3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Verbascum phlomoides. Based on a literature review very few articles have been published on Phlomoidoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042202542D          

 44 48  0  0  1  0            999 V2000
   -2.0470   -4.2338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679   -4.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7229   -5.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298   -5.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0819   -5.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8888   -5.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 20  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 39  1  1  0  0  0
 18 40  1  0  0  0  0
 23 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END


  Mrv1652309042202542D          

 44 48  0  0  1  0            999 V2000
   -2.0470   -4.2338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6610   -4.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679   -4.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7229   -5.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5298   -5.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0819   -5.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8888   -5.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 20  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
 24 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 39  1  1  0  0  0
 18 40  1  0  0  0  0
 23 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0185480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O[C@@H]4OC[C@@H](OC(=O)\C=C\C5=CC=C(O)C=C5)[C@H](O)[C@H]4O)C=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O15/c30-10-14-9-17(16-7-8-39-27(21(14)16)44-29-26(38)24(36)22(34)18(11-31)43-29)42-28-25(37)23(35)19(12-40-28)41-20(33)6-3-13-1-4-15(32)5-2-13/h1-9,16-19,21-32,34-38H,10-12H2/b6-3+/t16-,17+,18+,19+,21+,22+,23-,24-,25+,26+,27-,28-,29-/m0/s1

> <INCHI_KEY>
QMXKOUSEDUDBEY-LNYAFLLHSA-N

> <FORMULA>
C29H36O15

> <MOLECULAR_WEIGHT>
624.592

> <EXACT_MASS>
624.205420459

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
62.3271370132099

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5R,6S)-6-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-1.5920452096666677

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.939014745669844

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397333808625651

> <JCHEM_PKA_STRONGEST_BASIC>
-2.741513062783781

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
147.17620000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,5R,6S)-6-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -3.821  -7.903   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.358  -7.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.834  -8.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.340  -8.864   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.816 -10.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.322 -10.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.353  -9.504   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -12.859  -9.824   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0     -10.877  -8.039   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.371  -7.719   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.376  -5.294   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.869  -4.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.258   7.167   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.315  -7.583   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   43                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   41                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   40                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   40                                                  
CONECT   24   23   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37   24   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   18   23                                                  
CONECT   41   16   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   13   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₅

Average Mass

624.5920 Da

Monoisotopic Mass

624.20542 Da

IUPAC Name

(3R,4R,5R,6S)-6-{[(1S,4aR,5S,7aS)-7-(hydroxymethyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O[C@@H]4OC[C@@H](OC(=O)\C=C\C5=CC=C(O)C=C5)[C@H](O)[C@H]4O)C=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C29H36O15/c30-10-14-9-17(16-7-8-39-27(21(14)16)44-29-26(38)24(36)22(34)18(11-31)43-29)42-28-25(37)23(35)19(12-40-28)41-20(33)6-3-13-1-4-15(32)5-2-13/h1-9,16-19,21-32,34-38H,10-12H2/b6-3+/t16-,17+,18+,19+,21+,22+,23-,24-,25+,26+,27-,28-,29-/m0/s1

InChI Key

QMXKOUSEDUDBEY-LNYAFLLHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Verbascum phlomoides	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
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Primary alcohol
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.6	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.18 m³·mol⁻¹	ChemAxon
Polarizability	62.33 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

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

102445639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0185480)

MOL for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0185480 ((3r,4r,5r,6s)-6-{[(1s,4ar,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)