NP-MRD: Showing NP-Card for (1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate (NP0206125)

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Record Information

Version

2.0

Created at

2022-09-05 02:15:14 UTC

Updated at

2022-09-05 02:15:14 UTC

NP-MRD ID

NP0206125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate

Description

Wikstroelide L belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. (1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate is found in Wikstroemia retusa. Based on a literature review very few articles have been published on Wikstroelide L.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052204152D          

 46 51  0  0  1  0            999 V2000
   -8.1706    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3622    5.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2246    5.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0301    4.1440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2560    4.4889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9618    3.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1466    4.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2855    3.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5710    4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    3.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4276    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8592    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9896    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0361    2.9440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3635    2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6976    2.1702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1118    1.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9017    2.3872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1878    1.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5750    3.1447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7193    2.8660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9637    3.8725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1294    4.4366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704    4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8682    5.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1386    5.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    6.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8831    4.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7749    4.0224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3979    3.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5904    3.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5394    3.2833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1889    2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7644    4.0433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5767    4.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2653    4.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1674    3.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0237    4.3477    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 20  1  0  0  0  0
 21 20  1  1  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 37 36  1  6  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  1  0  0  0
  6 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
M  END


  Mrv1652309052204152D          

 46 51  0  0  1  0            999 V2000
   -8.1706    5.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3622    5.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2246    5.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0301    4.1440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2560    4.4889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9618    3.7080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1466    4.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2855    3.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5710    4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    3.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4276    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9986    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1448    2.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8592    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9896    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0361    2.9440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3635    2.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6976    2.1702    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1118    1.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9017    2.3872    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1878    1.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5750    3.1447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7193    2.8660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9637    3.8725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1294    4.4366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5704    4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8682    5.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1386    5.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    6.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8831    4.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7749    4.0224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3979    3.4815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5904    3.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5394    3.2833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1889    2.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7644    4.0433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5767    4.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2653    4.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1674    3.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0237    4.3477    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
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  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  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 20  1  0  0  0  0
 21 20  1  1  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 37 36  1  6  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 38  1  0  0  0  0
 38 39  1  1  0  0  0
  6 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
  4 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0206125

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC\C=C/C=C/[C@]12O[C@@H]3C4[C@@H]5O[C@]5(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]4(O1)[C@H](C)[C@@H](OC(C)=O)[C@@]3(O2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C36H50O10/c1-7-8-9-10-11-12-13-14-15-16-17-18-33-44-30-26-29-32(20-37,43-29)31(40)34(41)25(19-22(4)27(34)39)36(26,46-33)23(5)28(42-24(6)38)35(30,45-33)21(2)3/h15-19,23,25-26,28-31,37,40-41H,2,7-14,20H2,1,3-6H3/b16-15-,18-17+/t23-,25-,26?,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1

> <INCHI_KEY>
ADIURPPZKNTYEV-ZZAFHLMQSA-N

> <FORMULA>
C36H50O10

> <MOLECULAR_WEIGHT>
642.786

> <EXACT_MASS>
642.34039781

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.30998010785774

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,6S,7S,8R,10S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl acetate

> <JCHEM_LOGP>
5.220366460666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.32788824180362

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.646350410239352

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1497130859374955

> <JCHEM_POLAR_SURFACE_AREA>
144.28

> <JCHEM_REFRACTIVITY>
170.32229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6S,7S,8R,10S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -15.252  11.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.609   9.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.219   9.779   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -14.989   7.735   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -13.545   8.379   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0     -12.995   6.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.474   8.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.866   7.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.533   7.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.199   7.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.199   5.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.865   4.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.531   5.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.198   4.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.864   5.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.530   4.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.803   5.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.137   4.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.471   5.667   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -14.914   6.724   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -15.001   5.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.745   4.960   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.502   4.051   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -11.409   2.967   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -11.016   4.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.684   3.328   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.229   1.773   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.407   5.870   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.809   5.350   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.132   7.229   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.575   8.282   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -10.398   8.582   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.087   9.751   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -11.459   9.699   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -11.212  11.383   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -12.848   9.035   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -12.647   7.508   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -13.809   6.499   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -12.302   5.783   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -15.940   6.129   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -17.153   4.966   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -16.360   7.547   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -17.877   8.471   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -19.162   7.509   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -18.979   5.980   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -20.578   8.116   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21   42                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   20   39                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    6   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21   23   38                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26   28                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   37                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   30   38                                                  
CONECT   38   37   22   39   40                                             
CONECT   39   38    6                                                       
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40    4   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₀O₁₀

Average Mass

642.7860 Da

Monoisotopic Mass

642.34040 Da

IUPAC Name

(1R,2R,6S,7S,8R,10S,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1E,3Z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0^{1,11}.0^{2,6}.0^{8,10}.0^{12,16}]nonadec-3-en-17-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCC\C=C/C=C/[C@]12O[C@@H]3C4[C@@H]5O[C@]5(CO)[C@@H](O)[C@@]5(O)[C@@H](C=C(C)C5=O)[C@@]4(O1)[C@H](C)[C@@H](OC(C)=O)[C@@]3(O2)C(C)=C

InChI Identifier

InChI=1S/C36H50O10/c1-7-8-9-10-11-12-13-14-15-16-17-18-33-44-30-26-29-32(20-37,43-29)31(40)34(41)25(19-22(4)27(34)39)36(26,46-33)23(5)28(42-24(6)38)35(30,45-33)21(2)3/h15-19,23,25-26,28-31,37,40-41H,2,7-14,20H2,1,3-6H3/b16-15-,18-17+/t23-,25-,26?,28-,29+,30-,31-,32+,33-,34-,35+,36+/m1/s1

InChI Key

ADIURPPZKNTYEV-ZZAFHLMQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Wikstroemia retusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
Ortho ester
Dioxepane
Carboxylic acid orthoester
1,3-dioxepane
Meta-dioxane
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Orthocarboxylic acid derivative
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	5.22	ChemAxon
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	144.28 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	170.32 m³·mol⁻¹	ChemAxon
Polarizability	70.31 Å³	ChemAxon
Number of Rings	6	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

C00049035

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

101949528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate (NP0206125)

MOL for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

3D MOL for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

3D SDF for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

3D-SDF for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

PDB for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

3D PDB for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

SMILES for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

INCHI for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

Structure for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)

3D Structure for NP0206125 ((1r,2r,6s,7s,8r,10s,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-16-(prop-1-en-2-yl)-14-[(1e,3z)-trideca-1,3-dien-1-yl]-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl acetate)