NP-MRD: Showing NP-Card for (1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate (NP0325664)

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Record Information

Version

2.0

Created at

2022-09-12 06:34:53 UTC

Updated at

2022-09-12 06:34:54 UTC

NP-MRD ID

NP0325664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate

Description

(1R,2R,4S,6S,7S,8R,10S,11R,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadecan-17-yl acetate 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,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate is found in Daphne genkwa. Based on a literature review very few articles have been published on (1R,2R,4S,6S,7S,8R,10S,11R,12R,14S,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadecan-17-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122208342D          

 39 45  0  0  1  0            999 V2000
   -2.3454   -2.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825   -2.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -3.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534   -2.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8891   -1.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048   -0.9539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5583   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276    0.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    1.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465   -2.0371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9411   -1.3680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4360   -0.7080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0238   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9464    0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749    0.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8987    1.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    0.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0223    1.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    0.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137    1.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -0.1131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5017    0.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2360   -0.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.7633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1165   -1.3927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5097   -0.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -2.5364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9366   -3.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4614   -2.7524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9188   -3.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -4.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1677   -4.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -4.9643    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  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  1  0  0  0
  6 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END


  Mrv1652309122208342D          

 39 45  0  0  1  0            999 V2000
   -2.3454   -2.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825   -2.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -3.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5534   -2.0169    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8891   -1.2388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048   -0.9539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5583   -0.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276    0.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    1.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6465   -2.0371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9411   -1.3680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4360   -0.7080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0238   -0.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2285    0.0905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9464    0.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955    0.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749    0.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8987    1.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    0.0461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0223    1.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779    0.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137    1.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -0.1131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5017    0.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2360   -0.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4169   -0.7633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1165   -1.3927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5097   -0.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012   -2.5364    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9366   -3.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4614   -2.7524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9188   -3.5397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -4.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1677   -4.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -4.9643    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  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  1  0  0  0
  6 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0325664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2[C@](O)([C@H](O)[C@@]3(CO)O[C@H]3[C@@H]3[C@H]4O[C@@]5(O[C@]4([C@H](OC(C)=O)[C@@H](C)[C@]23O5)C(C)=C)C2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O10/c1-13(2)27-21(35-16(5)31)15(4)28-18-11-14(3)20(32)26(18,34)24(33)25(12-30)22(36-25)19(28)23(27)37-29(38-27,39-28)17-9-7-6-8-10-17/h6-10,14-15,18-19,21-24,30,33-34H,1,11-12H2,2-5H3/t14-,15+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28-,29+/m0/s1

> <INCHI_KEY>
KXQIRSPCAUQOEP-KSAXRJBNSA-N

> <FORMULA>
C29H34O10

> <MOLECULAR_WEIGHT>
542.581

> <EXACT_MASS>
542.215197295

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.43727511018557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.892802066

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.352819050601568

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.715592168260997

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1496971119732367

> <JCHEM_POLAR_SURFACE_AREA>
144.28

> <JCHEM_REFRACTIVITY>
132.0962

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.378  -4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.767  -4.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.067  -6.181   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.033  -3.765   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.660  -2.312   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.196  -1.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.042  -0.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.378  -0.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.225   1.241   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.538   2.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.806   2.364   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.157   0.968   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.021  -3.701   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.207  -3.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.757  -2.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.681  -1.322   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.778  -0.241   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.293   0.169   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.633   1.383   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.218   1.820   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.886   0.795   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.678   2.554   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.480   0.086   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.042   1.957   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.825   0.836   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.706   2.674   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.954  -0.211   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.670   0.302   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.307  -1.609   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.778  -1.425   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.217  -2.600   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.951  -1.101   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.562  -4.735   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.748  -5.856   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.861  -5.138   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.715  -6.607   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.199  -8.104   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.313  -8.397   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.209  -9.267   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   14   35                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   13   32                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    6   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16   31                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   18                                                       
CONECT   18   17   16   19   21                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   15   32   33                                             
CONECT   32   31    6                                                       
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    4   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4S,6S,7S,8R,10S,11R,12R,14S,16S,17R,18R)-6,7-Dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0,.0,.0,.0,]nonadecan-17-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₄O₁₀

Average Mass

542.5810 Da

Monoisotopic Mass

542.21520 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2[C@](O)([C@H](O)[C@@]3(CO)O[C@H]3[C@@H]3[C@H]4O[C@@]5(O[C@]4([C@H](OC(C)=O)[C@@H](C)[C@]23O5)C(C)=C)C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C29H34O10/c1-13(2)27-21(35-16(5)31)15(4)28-18-11-14(3)20(32)26(18,34)24(33)25(12-30)22(36-25)19(28)23(27)37-29(38-27,39-28)17-9-7-6-8-10-17/h6-10,14-15,18-19,21-24,30,33-34H,1,11-12H2,2-5H3/t14-,15+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28-,29+/m0/s1

InChI Key

KXQIRSPCAUQOEP-KSAXRJBNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphne genkwa	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
1,3-dioxepane
Carboxylic acid orthoester
Ortho ester
Dioxepane
Meta-dioxane
Monocyclic benzene moiety
Benzenoid
Meta-dioxolane
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Orthocarboxylic acid derivative
Ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Monocarboxylic acid or derivatives
Ether
Oxirane
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
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	1.89	ChemAxon
pKa (Strongest Acidic)	11.72	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	5	ChemAxon
Refractivity	132.1 m³·mol⁻¹	ChemAxon
Polarizability	55.44 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

163010592

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,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate (NP0325664)

MOL for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

3D MOL for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

3D SDF for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

3D-SDF for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

PDB for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

3D PDB for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

SMILES for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

INCHI for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

Structure for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)

3D Structure for NP0325664 ((1r,2r,4s,6s,7s,8r,10s,11r,12r,14s,16s,17r,18r)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadecan-17-yl acetate)