NP-MRD: Showing NP-Card for 22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate (NP0226166)

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Record Information

Version

2.0

Created at

2022-09-06 05:07:23 UTC

Updated at

2022-09-06 05:07:23 UTC

NP-MRD ID

NP0226166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate

Description

22-Hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]Pentacos-14-en-8-yl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 22-Hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]Pentacos-14-en-8-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161520112D          

 50 56  0  0  0  0            999 V2000
    0.1615   -1.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870    0.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641    0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133    0.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258   -0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440    0.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9228   -0.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1425    0.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7031   -1.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244   -2.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8932   -2.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2820   -1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0805   -1.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8790   -1.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4578   -1.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6775   -1.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4760   -0.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0549   -1.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8352   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4140   -2.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366   -2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6957   -0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4943    0.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731   -0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534   -1.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4322   -1.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125   -2.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7913   -3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307   -1.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8095   -2.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4504   -0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2489   -0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8716   -0.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0913    0.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1169    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7964    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7741    1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184    0.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396    0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9411    0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    0.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
  7 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 25 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  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
 21 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 10 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END


  Mrv1533004161520112D          

 50 56  0  0  0  0            999 V2000
    0.1615   -1.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994   -0.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6870    0.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2641    0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1133    0.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3258   -0.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5455    0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3440    0.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9228   -0.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1425    0.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7031   -1.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046   -1.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244   -2.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8932   -2.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7106   -1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5878   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2820   -1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0805   -1.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0987   -0.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8790   -1.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4578   -1.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6775   -1.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4760   -0.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0549   -1.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8352   -2.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4140   -2.8862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0366   -2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6957   -0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4943    0.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731   -0.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8534   -1.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4322   -1.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125   -2.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7913   -3.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2307   -1.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8095   -2.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4504   -0.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2489   -0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8716   -0.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0913    0.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1169    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7964    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7741    1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184    0.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7396    0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9411    0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    0.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
  7 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 25 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  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 32 41  1  0  0  0  0
 41 42  1  0  0  0  0
 30 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
 21 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 10 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1COC(O)C23CCC4(C)C(CCC5C4(C)CCC4C(C)(C)C(OC6OC(CO)C(O)C(O)C6O)C(CC54CO)OC(C)=O)=C2C(=O)CC13

> <INCHI_IDENTIFIER>
InChI=1S/C38H58O12/c1-18-16-47-33(46)38-12-11-35(5)20(27(38)22(42)13-21(18)38)7-8-26-36(35,6)10-9-25-34(3,4)31(23(48-19(2)41)14-37(25,26)17-40)50-32-30(45)29(44)28(43)24(15-39)49-32/h18,21,23-26,28-33,39-40,43-46H,7-17H2,1-6H3

> <INCHI_KEY>
VQSOJBKVEUZDMN-UHFFFAOYSA-N

> <FORMULA>
C38H58O12

> <MOLECULAR_WEIGHT>
706.87

> <EXACT_MASS>
706.392827308

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
76.70514590046375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.1517702130000014

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.355274119358477

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.711466987340366

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7609552136177973

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
178.25460000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate

> <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       0.301  -1.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.679  -1.289   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.771   0.248   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.149   0.937   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.226   0.023   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.812   0.777   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.341  -1.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.752   0.035   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.242   0.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.323  -0.675   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.733   0.809   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.913  -2.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.422  -2.546   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.712  -3.913   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.401  -5.291   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.193  -3.660   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.964  -2.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.993  -3.257   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.484  -2.870   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.894  -1.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.384  -0.998   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.974  -2.483   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.055  -3.580   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.465  -2.096   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.955  -1.709   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.036  -2.806   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.626  -4.290   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.706  -5.388   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.135  -4.677   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.365  -0.224   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.856   0.163   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.936  -0.934   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.526  -2.419   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      17.607  -3.516   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.197  -5.001   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.277  -6.098   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      19.097  -3.129   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      20.178  -4.227   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      19.507  -1.645   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      20.998  -1.258   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      18.427  -0.547   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      18.837   0.937   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      13.285   0.873   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.553   1.747   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.645   2.274   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.794   0.486   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.714   1.584   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.223   1.196   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.813  -0.288   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.584   1.235   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   49                                             
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    2    7                                                  
CONECT   18   12   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   49                                                  
CONECT   21   20   22   24   46                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   41                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   34   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   32   42                                                  
CONECT   42   41                                                            
CONECT   43   30   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   21   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   10   20   50                                             
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

View in JSmol

Synonyms

Value	Source
22-Hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0,.0,.0,.0,]pentacos-14-en-8-yl acetic acid	Generator
22-Hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetic acid	Generator

Chemical Formula

C₃₈H₅₈O₁₂

Average Mass

706.8700 Da

Monoisotopic Mass

706.39283 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1COC(O)C23CCC4(C)C(CCC5C4(C)CCC4C(C)(C)C(OC6OC(CO)C(O)C(O)C6O)C(CC54CO)OC(C)=O)=C2C(=O)CC13

InChI Identifier

InChI=1S/C38H58O12/c1-18-16-47-33(46)38-12-11-35(5)20(27(38)22(42)13-21(18)38)7-8-26-36(35,6)10-9-25-34(3,4)31(23(48-19(2)41)14-37(25,26)17-40)50-32-30(45)29(44)28(43)24(15-39)49-32/h18,21,23-26,28-33,39-40,43-46H,7-17H2,1-6H3

InChI Key

VQSOJBKVEUZDMN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
18-hydroxysteroid
Hydroxysteroid
15-oxosteroid
Oxosteroid
Steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Ketone
Carboxylic acid ester
Hemiacetal
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Primary alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
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	1.52	ALOGPS
logP	1.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	178.25 m³·mol⁻¹	ChemAxon
Polarizability	76.71 Å³	ChemAxon
Number of Rings	7	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

73092065

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate (NP0226166)

MOL for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

3D MOL for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

3D SDF for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

3D-SDF for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

PDB for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

3D PDB for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

SMILES for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

INCHI for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

Structure for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)

3D Structure for NP0226166 (22-hydroxy-10-(hydroxymethyl)-1,2,6,6,19-pentamethyl-16-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-21-oxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁸,²³]pentacos-14-en-8-yl acetate)