NP-MRD: Showing NP-Card for Epoxysiderol (NP0081345)

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Record Information

Version

2.0

Created at

2022-04-29 02:18:53 UTC

Updated at

2022-04-29 02:18:53 UTC

NP-MRD ID

NP0081345

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epoxysiderol

Description

Epoxysiderol belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Epoxysiderol is found in Sideritis arguta, Sideritis sicula and Sideritis spp.. Epoxysiderol was first documented in 2021 (PMID: 34437915). Based on a literature review very few articles have been published on Epoxysiderol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204182D          

 26 30  0  0  1  0            999 V2000
    3.2710    1.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968    0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    0.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9845    0.5884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8587    1.4038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5019    1.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.7286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3862    1.1737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5679    0.3497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3422    0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -0.1916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -1.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199   -1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    0.9188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9689    1.5778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5010    2.3208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1530    2.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915    0.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000    1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    2.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -0.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -0.4893    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
  1  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
  4 10  1  1  0  0  0
  9 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
  8 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
  7 19  1  1  0  0  0
 17 20  1  1  0  0  0
  8 20  1  1  0  0  0
 16 21  1  0  0  0  0
 15 21  1  1  0  0  0
 16 22  1  6  0  0  0
  5 23  1  1  0  0  0
  3 24  1  6  0  0  0
 24 25  1  0  0  0  0
  3 26  1  1  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
    3.4390    3.7774   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697    3.0545    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    3.3119    1.3595 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142    2.0683   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7360    1.2773    0.2798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6072    1.5480   -0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5260    0.3638   -0.3723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9656    0.7019   -0.4546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6696    0.9815    0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    1.8805   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5407    2.2141   -1.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6760   -0.4862   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192   -1.7274   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1099   -1.9256    0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1724   -0.7640    0.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2780   -0.5059    1.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -1.1965    0.0801 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6309   -2.5308    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0778   -2.7385    0.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937   -1.5153    1.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1111   -0.3148    1.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419   -0.1083    0.2560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2938   -0.3108   -0.8506 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5218    0.4149   -0.4295 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3236   -1.0339   -0.3466 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4605   -1.7505   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    3.3009   -0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    4.7884   -0.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1098    3.7963   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934    1.6996    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.0598   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1585    2.3009    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832   -0.0474   -1.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5010    1.7331    0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2458    0.0711    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612    1.4212    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6459    2.7765   -1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725    1.6393   -2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606    3.0441   -0.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8992   -0.2817   -2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624   -0.6782   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5388   -2.5941   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1355   -1.8227   -1.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9146   -1.9980    1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114   -2.8941    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871    0.4715    2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.2527    2.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3249   -0.7463    2.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003   -1.2923   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0551   -2.8400    1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398   -3.3429   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -3.3410    0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2211   -3.3843    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -1.6965    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5757   -0.4047    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123    0.5519    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    0.0141   -1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457   -1.7363   -2.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4103   -1.2113   -0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6052   -2.7897   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 22  5  1  0
 25 23  1  0
 15  7  1  0
 22 17  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  1
  6 31  1  0
  6 32  1  0
  7 33  1  6
  9 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  6
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  1
 21 55  1  0
 21 56  1  0
 23 57  1  6
 26 58  1  0
 26 59  1  0
 26 60  1  0
M  END


  Mrv1652304292204182D          

 26 30  0  0  1  0            999 V2000
    3.2710    1.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3968    0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    0.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9845    0.5884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8587    1.4038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5019    1.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781    1.7286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3862    1.1737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5679    0.3497    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3422    0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -0.1916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027   -1.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -1.2700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199   -1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    0.9188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9689    1.5778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5010    2.3208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1530    2.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915    0.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000    1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    2.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474   -0.3712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4818   -0.4893    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
  1  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
  4 10  1  1  0  0  0
  9 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
  8 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
  7 19  1  1  0  0  0
 17 20  1  1  0  0  0
  8 20  1  1  0  0  0
 16 21  1  0  0  0  0
 15 21  1  1  0  0  0
 16 22  1  6  0  0  0
  5 23  1  1  0  0  0
  3 24  1  6  0  0  0
 24 25  1  0  0  0  0
  3 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081345

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2[C@@](C)(CO)CCC[C@@]2(C)[C@@H]2CC[C@@H]3C[C@]12[C@H]1O[C@@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-13(24)25-17-10-16-19(2,12-23)8-5-9-20(16,3)15-7-6-14-11-22(15,17)18-21(14,4)26-18/h14-18,23H,5-12H2,1-4H3/t14-,15+,16-,17+,18+,19-,20+,21+,22-/m1/s1

> <INCHI_KEY>
YSPZBZPFWJQSQN-SAFIEXBJSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
40.958761498911265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,5S,9R,10S,13R,14S,16R)-5-(hydroxymethyl)-5,9,14-trimethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-2-yl acetate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.820827363333334

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592292898998593

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2271000001535488

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
97.69009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5S,9R,10S,13R,14S,16R)-5-(hydroxymethyl)-5,9,14-trimethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.106   3.027   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.341   1.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.140   0.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.704   1.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.470   2.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.670   3.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.012   3.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.721   2.191   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   0.653   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.506   0.114   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.102  -0.358   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.192  -1.869   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.648  -2.371   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.970  -2.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.882   1.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.809   2.945   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.935   4.332   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.286   5.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.800   4.855   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.005   3.309   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.411   1.528   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.173   3.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.253   4.145   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.062  -0.693   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.591  -0.511   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.633  -0.913   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24   26                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   23                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   19                                                  
CONECT    8    7    9   15   20                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8   16   21                                                  
CONECT   16   15   17   21   22                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7                                                       
CONECT   20   17    8                                                       
CONECT   21   16   15                                                       
CONECT   22   16                                                            
CONECT   23    5                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(1R,2S,4S,5S,9R,10S,13R,14S,16R)-5-(hydroxymethyl)-5,9,14-trimethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-2-yl acetate

Traditional Name

(1R,2S,4S,5S,9R,10S,13R,14S,16R)-5-(hydroxymethyl)-5,9,14-trimethyl-15-oxapentacyclo[11.3.1.0^{1,10}.0^{4,9}.0^{14,16}]heptadecan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2[C@@](C)(CO)CCC[C@@]2(C)[C@@H]2CC[C@@H]3C[C@]12[C@H]1O[C@@]31C

InChI Identifier

InChI=1S/C22H34O4/c1-13(24)25-17-10-16-19(2,12-23)8-5-9-20(16,3)15-7-6-14-11-22(15,17)18-21(14,4)26-18/h14-18,23H,5-12H2,1-4H3/t14-,15+,16-,17+,18+,19-,20+,21+,22-/m1/s1

InChI Key

YSPZBZPFWJQSQN-SAFIEXBJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sideritis arguta	Plant	KNApSAcK
Sideritis sicula	Plant	KNApSAcK
Sideritis spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Oxane
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxygen compound
Organooxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Carbonyl group
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	3	ALOGPS
logP	2.82	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.69 m³·mol⁻¹	ChemAxon
Polarizability	40.96 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00047223

Chemspider ID

103884237

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102445841

PDB ID

Not Available

ChEBI ID

174852

Good Scents ID

Not Available

References

General References

Fiengo L, Lauro G, Bellone ML, Bifulco G, Dal Piaz F, De Tommasi N: The plant diterpene epoxysiderol targets Hsp70 in cancer cells, affecting its ATPase activity and reducing its translocation to plasma membrane. Int J Biol Macromol. 2021 Oct 31;189:262-270. doi: 10.1016/j.ijbiomac.2021.08.138. Epub 2021 Aug 23. [PubMed:34437915 ]

Showing NP-Card for Epoxysiderol (NP0081345)

MOL for NP0081345 (Epoxysiderol)

3D MOL for NP0081345 (Epoxysiderol)

3D SDF for NP0081345 (Epoxysiderol)

3D-SDF for NP0081345 (Epoxysiderol)

PDB for NP0081345 (Epoxysiderol)

3D PDB for NP0081345 (Epoxysiderol)

SMILES for NP0081345 (Epoxysiderol)

INCHI for NP0081345 (Epoxysiderol)

Structure for NP0081345 (Epoxysiderol)

3D Structure for NP0081345 (Epoxysiderol)