NP-MRD: Showing NP-Card for (1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate (NP0160529)

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Record Information

Version

2.0

Created at

2022-09-02 18:30:19 UTC

Updated at

2022-09-02 18:30:19 UTC

NP-MRD ID

NP0160529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate

Description

(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-6,10,13-trimethyl-2-methylidene-4-oxo-16-(propan-2-yl)tetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]Octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate is found in Dictyochaeta simplex. Based on a literature review very few articles have been published on (1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-6,10,13-trimethyl-2-methylidene-4-oxo-16-(propan-2-yl)tetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]Octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309022220302D          

 40 43  0  0  1  0            999 V2000
    3.7021    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -0.8150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8934   -0.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -0.4428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3818    0.0077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4235    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1580    1.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238   -0.5103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8203   -0.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4047   -0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1925   -1.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2012   -0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7856   -1.2453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3679   -0.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2032   -1.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5473   -1.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9055   -1.2393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.4164    0.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7993   -0.6186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0323    0.1728    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  1  1  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
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 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
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 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
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 27 26  1  6  0  0  0
  3 27  1  0  0  0  0
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 28 30  2  0  0  0  0
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 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END

     RDKit          3D

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 34 88  1  0
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 34 90  1  0
 36 91  1  0
M  END

  Mrv1652309022220302D          

 40 43  0  0  1  0            999 V2000
    3.7021    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -0.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110   -0.8150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8934   -0.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6906   -0.4428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3818    0.0077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4235    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1580    1.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309    1.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0238   -0.5103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8203   -0.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4047   -0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1925   -1.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2012   -0.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7856   -1.2453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3679   -0.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2032   -1.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3699   -1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1665   -1.6128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3786   -0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7508   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5473   -1.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295   -1.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9055   -1.2393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2025   -2.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232   -1.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5259   -1.6115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1146   -2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180   -2.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3181   -2.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029   -2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881   -1.3338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5808   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931   -0.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7780    0.0680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2462   -0.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4164    0.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7993   -0.6186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0323    0.1728    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  1  1  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 27 26  1  6  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0160529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C[C@@](C)(O)CC(=O)O[C@@H]1C[C@]2(C)C[C@H]3[C@H](C[C@H]2[C@H]1C(C)C)C(=C)[C@@]1(O)[C@@H](C\C=C3\C)C(C)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H52O6/c1-10-19(4)14-33(9,38)17-28(35)40-27-16-32(8)15-24-20(5)11-12-25-21(6)30(36)31(37)34(25,39)22(7)23(24)13-26(32)29(27)18(2)3/h11,18-19,23-27,29,36,38-39H,7,10,12-17H2,1-6,8-9H3/b20-11-/t19-,23+,24+,25-,26-,27+,29+,32-,33+,34+/m0/s1

> <INCHI_KEY>
XCBZBPKHZFIJGF-AMKJMDMHSA-N

> <FORMULA>
C34H52O6

> <MOLECULAR_WEIGHT>
556.784

> <EXACT_MASS>
556.376389394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
64.6522588154277

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-6,10,13-trimethyl-2-methylidene-4-oxo-16-(propan-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{13,17}]octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.882988689666668

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.596392319794344

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.654146341143628

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8939342052833332

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
158.80520000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0^{3,7}.0^{13,17}]octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.911   0.774   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.712  -0.754   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.047  -1.521   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.134  -0.430   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.623  -0.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.913   0.014   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.991   1.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.362   2.254   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.698   2.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.111  -0.953   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.598  -0.552   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.689  -1.639   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.293  -3.127   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.176  -1.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.266  -2.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.353  -1.234   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.179  -3.415   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      19.357  -3.412   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.844  -3.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.240  -1.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.935  -4.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.422  -3.696   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.562  -2.391   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.024  -2.313   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.578  -3.750   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.937  -3.404   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.448  -3.008   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.681  -4.343   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.620  -5.563   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.194  -4.744   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.859  -3.977   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.458  -2.490   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.951  -2.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.808  -3.205   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.787  -0.641   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.452   0.127   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.193  -0.012   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.511   1.495   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.225  -1.155   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.660   0.323   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23    5   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   32   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-Dihydroxy-6,10,13-trimethyl-2-methylidene-4-oxo-16-(propan-2-yl)tetracyclo[9.7.0.0,.0,]octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoic acid	Generator

Chemical Formula

C₃₄H₅₂O₆

Average Mass

556.7840 Da

Monoisotopic Mass

556.37639 Da

IUPAC Name

(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-6,10,13-trimethyl-2-methylidene-4-oxo-16-(propan-2-yl)tetracyclo[9.7.0.0^{3,7}.0^{13,17}]octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate

Traditional Name

(1S,3S,7S,9Z,11S,13S,15R,16R,17S)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0^{3,7}.0^{13,17}]octadeca-5,9-dien-15-yl (3R,5S)-3-hydroxy-3,5-dimethylheptanoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C[C@@](C)(O)CC(=O)O[C@@H]1C[C@]2(C)C[C@H]3[C@H](C[C@H]2[C@H]1C(C)C)C(=C)[C@@]1(O)[C@@H](C\C=C3\C)C(C)=C(O)C1=O

InChI Identifier

InChI=1S/C34H52O6/c1-10-19(4)14-33(9,38)17-28(35)40-27-16-32(8)15-24-20(5)11-12-25-21(6)30(36)31(37)34(25,39)22(7)23(24)13-26(32)29(27)18(2)3/h11,18-19,23-27,29,36,38-39H,7,10,12-17H2,1-6,8-9H3/b20-11-/t19-,23+,24+,25-,26-,27+,29+,32-,33+,34+/m0/s1

InChI Key

XCBZBPKHZFIJGF-AMKJMDMHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dictyochaeta simplex	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.01	ALOGPS
logP	5.88	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.65	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	158.81 m³·mol⁻¹	ChemAxon
Polarizability	64.65 Å³	ChemAxon
Number of Rings	4	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

162849106

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate (NP0160529)

MOL for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

3D MOL for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

3D SDF for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

3D-SDF for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

PDB for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

3D PDB for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

SMILES for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

INCHI for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

Structure for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)

3D Structure for NP0160529 ((1s,3s,7s,9z,11s,13s,15r,16r,17s)-3,5-dihydroxy-16-isopropyl-6,10,13-trimethyl-2-methylidene-4-oxotetracyclo[9.7.0.0³,⁷.0¹³,¹⁷]octadeca-5,9-dien-15-yl (3r,5s)-3-hydroxy-3,5-dimethylheptanoate)