NP-MRD: Showing NP-Card for (1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate (NP0206790)

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Record Information

Version

2.0

Created at

2022-09-05 03:10:23 UTC

Updated at

2022-09-05 03:10:23 UTC

NP-MRD ID

NP0206790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate

Description

Siderol 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. (1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate is found in Sideritis pungens, Sideritis sipylea and Sideritis trojana. (1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate was first documented in 2006 (PMID: 17962756). Based on a literature review a small amount of articles have been published on Siderol (PMID: 32443927) (PMID: 16557612) (PMID: 35918468) (PMID: 23297676).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052205102D          

 25 28  0  0  1  0            999 V2000
    0.8527    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670    1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    2.5447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    1.9001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5178    2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    1.4259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8663    1.5848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5693    2.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2950    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    0.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1416    0.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320    0.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    0.6454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5231   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699    0.4831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805   -0.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486   -0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461    0.0607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8861    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578    1.1181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5246    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    0.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
  5 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    0.8080    4.7242    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0053    3.4264    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    3.4153    1.9716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433    2.2152    0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    1.0069    1.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5729    0.4096    1.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049    0.1684    0.2011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7817    0.0762    0.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1639   -0.2027    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4449    1.4334    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8184    1.3472    0.2101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4538   -0.9354   -0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8492   -1.1406   -1.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3962   -0.8752   -1.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -0.9407   -0.5990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8610   -2.3024   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7656   -0.5544   -0.8756 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5362   -1.5966   -1.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.2597   -0.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369   -1.5952    0.3625 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -1.0680    1.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4853   -0.0222    0.3168 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7762    0.5707   -0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -0.3010   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2348   -0.1244   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453    5.3015    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050    4.6106   -0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7073    5.3498    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3287    1.2357    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682   -0.5359    2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.1485    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040    1.0986   -0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1473   -0.6993    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3745   -0.7738    2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2682    0.7532    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2341    1.7689   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0699    2.1185    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037    0.9207    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5714   -1.8769    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5238   -0.6017   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0865   -2.1852   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738   -0.4881   -2.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914    0.1676   -2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8776   -1.5416   -2.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686   -2.9268   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491   -2.3780    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767   -2.9346   -0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733    0.3304   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9305   -1.2349   -2.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7994   -2.3994   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842   -3.3240   -0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5454   -2.3941   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168   -2.2626    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -0.5526    2.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3366   -1.7962    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    1.5484   -0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5119   -0.4747   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045   -0.7549    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5723    0.9076   -0.0726 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
 21 22  1  0
 22 23  1  6
 23 24  2  0
 24 25  1  0
 22  5  1  0
 15  7  1  0
 22 17  1  0
 24 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  1
  6 30  1  0
  6 31  1  0
  7 32  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  1
 21 54  1  0
 21 55  1  0
 23 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
M  END


  Mrv1652309052205102D          

 25 28  0  0  1  0            999 V2000
    0.8527    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    2.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670    1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    2.5447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6984    1.9001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5178    2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568    1.4259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8663    1.5848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5693    2.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5727    2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2950    1.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4087    0.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1416    0.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320    0.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    0.6454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5231   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699    0.4831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805   -0.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9486   -0.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461    0.0607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8861    0.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578    1.1181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5246    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1085    0.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
  5 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206790

> <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@]12C=C3C

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-14-11-22-12-16(14)6-7-17(22)21(4)9-5-8-20(3,13-23)18(21)10-19(22)25-15(2)24/h11,16-19,23H,5-10,12-13H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+/m1/s1

> <INCHI_KEY>
OFNWUWHDGCNABD-CSGHFTSRSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.511

> <EXACT_MASS>
346.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.42503670683804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4S,5S,9R,10S,13R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-en-2-yl acetate

> <JCHEM_LOGP>
3.4877476816666677

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592292799187035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.227530403886559

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
99.16059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5S,9R,10S,13R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadec-14-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.592   5.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.553   4.519   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.992   3.085   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.076   4.750   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.037   3.547   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.567   3.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.573   2.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.084   2.958   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.529   4.395   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.402   3.754   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.751   3.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.096   1.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.598   0.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.086   0.044   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.074   1.205   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.576  -0.253   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.544   0.902   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.190  -0.682   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.637  -1.052   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.513   0.113   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.521   1.061   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.401   2.087   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.846   2.718   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.731   1.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.202   1.717   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   17   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5110 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

Not Available

Traditional Name

Not Available

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@]12C=C3C

InChI Identifier

InChI=1S/C22H34O3/c1-14-11-22-12-16(14)6-7-17(22)21(4)9-5-8-20(3,13-23)18(21)10-19(22)25-15(2)24/h11,16-19,23H,5-10,12-13H2,1-4H3/t16-,17+,18-,19+,20-,21+,22+/m1/s1

InChI Key

OFNWUWHDGCNABD-CSGHFTSRSA-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
Sideritis pungens	LOTUS Database	35616633
Sideritis sipylea	LOTUS Database	35616633
Sideritis trojana	LOTUS Database	35616633

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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Iron

METLIN ID

Not Available

PubChem Compound

12315548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tomou EM, Chatziathanasiadou MV, Chatzopoulou P, Tzakos AG, Skaltsa H: NMR-Based Chemical Profiling, Isolation and Evaluation of the Cytotoxic Potential of the Diterpenoid Siderol from Cultivated Sideritis euboea Heldr. Molecules. 2020 May 20;25(10). pii: molecules25102382. doi: 10.3390/molecules25102382. [PubMed:32443927 ]
Kilic T: Isolation and biological activity of new and known isolation and biological activity of new and known diterpenoids from Sideritis stricta Boiss. & Heldr. Molecules. 2006 Mar 29;11(4):257-62. doi: 10.3390/11040257. [PubMed:17962756 ]
Logoglu E, Arslan S, Oktemer A, Sakoyan I: Biological activities of some natural compounds from Sideritis sipylea Boiss. Phytother Res. 2006 Apr;20(4):294-7. doi: 10.1002/ptr.1855. [PubMed:16557612 ]
Koromili M, Kapourani A, Koletti A, Papandreou G, Assimopoulou AN, Lazari D, Barmpalexis P: Preparation and Evaluation of Siderol Amorphous Solid Dispersions: Selection of Suitable Matrix/Carrier. AAPS PharmSciTech. 2022 Aug 3;23(6):214. doi: 10.1208/s12249-022-02368-9. [PubMed:35918468 ]
Venditti A, Bianco A, Maggi F, Nicoletti M: Polar constituents composition of endemic Sideritis italica (MILL.) GREUTER et BURTER from Central Italy. Nat Prod Res. 2013 Aug;27(15):1408-12. doi: 10.1080/14786419.2012.744991. Epub 2013 Jan 9. [PubMed:23297676 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate (NP0206790)

MOL for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

3D MOL for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

3D SDF for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

3D-SDF for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

PDB for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

3D PDB for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

SMILES for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

INCHI for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

Structure for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)

3D Structure for NP0206790 ((1r,2s,4s,5s,9r,10s,13r)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-2-yl acetate)