NP-MRD: Showing NP-Card for tenuifolin E (NP0043241)

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Record Information

Version

2.0

Created at

2021-06-21 00:42:24 UTC

Updated at

2021-06-30 00:18:49 UTC

NP-MRD ID

NP0043241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tenuifolin E

Provided By

JEOL Database JEOL Logo

Description

Tenuifolin E 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. tenuifolin E is found in Isodon tenuifolius. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on Tenuifolin E (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454) (PMID: 26389451) (PMID: 26389436).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102423D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102423D          

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    3.0254   -3.2027   -2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -5.1458   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -5.5018   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9552   -2.4675    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5970   -2.6723   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0669   -4.0486    0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -3.7578    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -4.4835    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -5.2371    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335   -2.6358    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    0.2032    3.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -1.0804    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    1.5390    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832    2.2164    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.3873    2.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.4168    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0  0  0  0
  3  4  1  0  0  0  0
 11 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
 12 14  1  0  0  0  0
 17 48  1  1  0  0  0
  8  7  1  0  0  0  0
 14 15  1  6  0  0  0
 17 18  1  0  0  0  0
  8  9  1  6  0  0  0
 18 20  1  0  0  0  0
 14 16  1  0  0  0  0
 21 20  1  1  0  0  0
  5  6  1  0  0  0  0
 14 17  1  0  0  0  0
 12 13  1  0  0  0  0
  8 10  1  0  0  0  0
  7 32  1  1  0  0  0
  7 21  1  0  0  0  0
 21 23  1  0  0  0  0
  8 17  1  0  0  0  0
  3  2  1  0  0  0  0
 23  2  1  0  0  0  0
 21 22  1  0  0  0  0
  2  1  2  3  0  0  0
 23 24  1  0  0  0  0
 22  3  1  0  0  0  0
 18 19  2  0  0  0  0
 11 38  1  0  0  0  0
 11 39  1  0  0  0  0
 12 40  1  6  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
  3 27  1  6  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  6  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
  6 31  1  0  0  0  0
 13 41  1  0  0  0  0
 23 53  1  1  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
 24 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11C([H])([H])C(=O)[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(O[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-10-11-7-12(21)16-19(4)6-5-14(23)18(2,3)15(19)13(22)9-20(16,8-11)17(10)24/h11-12,14-17,21,23-24H,1,5-9H2,2-4H3/t11-,12+,14+,15-,16+,17-,19-,20+/m1/s1

> <INCHI_KEY>
WSZHSVSVZWABOB-ANWSMTEOSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.66232758399839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,6S,9S,10S,11S,13S,15R)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-3-one

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.0784081510000005

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.595440404689217

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.960919010370318

> <JCHEM_PKA_STRONGEST_BASIC>
-2.847195825583319

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
90.78319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6S,9S,10S,11S,13S,15R)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -1.6239    3.3441    1.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    2.4537    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354    2.5992    0.1553 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4557    2.0224   -1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0289    0.5587   -1.2769 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4640    0.5495   -1.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160   -0.3498   -0.1303 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7104   -1.3297   -0.5644 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9157   -0.5507   -1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -2.2967   -1.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929   -3.5126   -1.9344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869   -4.3092   -0.6618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1554   -4.8794   -0.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0089   -3.4380    0.4684 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4760   -3.1240    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -4.2740    1.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835   -2.1968    0.6847 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4603   -1.2536    1.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -1.1541    2.2939 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3249   -0.4041    2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    0.4697    1.2084 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6043    1.7226    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    1.1578    1.7404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7128    0.3747    1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5978    4.2642    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4949    3.1624    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9870    3.6352    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    2.0936   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2461    2.6544   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    0.1357   -2.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160    1.0779   -1.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990   -1.0497    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -1.1676   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    0.2673   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -0.1375   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -1.7637   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -2.6634   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5782   -4.1602   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -3.2027   -2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -5.1458   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -5.5018   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9552   -2.4675    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5970   -2.6723   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0669   -4.0486    0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -3.7578    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -4.4835    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -5.2371    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335   -2.6358    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    0.2032    3.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -1.0804    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    1.5390    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832    2.2164    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.3873    2.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.4168    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  3  4  1  0
 11 10  1  0
  4  5  1  0
  5  7  1  0
 12 14  1  0
 17 48  1  1
  8  7  1  0
 14 15  1  6
 17 18  1  0
  8  9  1  6
 18 20  1  0
 14 16  1  0
 21 20  1  1
  5  6  1  0
 14 17  1  0
 12 13  1  0
  8 10  1  0
  7 32  1  1
  7 21  1  0
 21 23  1  0
  8 17  1  0
  3  2  1  0
 23  2  1  0
 21 22  1  0
  2  1  2  3
 23 24  1  0
 22  3  1  0
 18 19  2  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 10 36  1  0
 10 37  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
  3 27  1  6
  4 28  1  0
  4 29  1  0
  5 30  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
  6 31  1  0
 13 41  1  0
 23 53  1  1
  1 25  1  0
  1 26  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.624   3.344   1.022  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.625   2.454   0.969  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.635   2.599   0.155  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.456   2.022  -1.255  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.029   0.559  -1.277  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.464   0.550  -1.169  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.516  -0.350  -0.130  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.710  -1.330  -0.564  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.916  -0.551  -1.131  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.193  -2.297  -1.676  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.093  -3.513  -1.934  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.387  -4.309  -0.662  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.155  -4.879  -0.209  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.009  -3.438   0.468  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.476  -3.124   0.110  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.045  -4.274   1.777  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.083  -2.197   0.685  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.460  -1.254   1.820  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.588  -1.154   2.294  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.325  -0.404   2.327  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.749   0.470   1.208  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.604   1.723   0.946  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.553   1.158   1.740  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.713   0.375   1.553  0.00  0.00           O+0
HETATM   25  H   UNK     0      -1.598   4.264   0.448  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.495   3.162   1.646  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.987   3.635   0.111  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.417   2.094  -1.775  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.246   2.654  -1.814  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.183   0.136  -2.261  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.816   1.078  -1.908  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.299  -1.050   0.113  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.556  -1.168  -1.763  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.602   0.267  -1.781  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.555  -0.138  -0.348  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.074  -1.764  -2.626  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.194  -2.663  -1.405  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.578  -4.160  -2.656  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.025  -3.203  -2.416  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.055  -5.146  -0.900  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.850  -5.502  -0.892  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.955  -2.467   0.840  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.597  -2.672  -0.873  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.067  -4.049   0.087  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.594  -3.758   2.571  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.040  -4.484   2.157  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.543  -5.237   1.612  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.133  -2.636   1.034  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.686   0.203   3.166  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.562  -1.080   2.732  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.531   1.539   0.404  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.883   2.216   1.888  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.459   1.387   2.809  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.924   0.417   0.595  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    3   23    1                                                  
CONECT    3    4    2   22   27                                             
CONECT    4    3    5   28   29                                             
CONECT    5    4    7    6   30                                             
CONECT    6    5   31                                                       
CONECT    7    5    8   32   21                                             
CONECT    8    7    9   10   17                                             
CONECT    9    8   33   34   35                                             
CONECT   10   11    8   36   37                                             
CONECT   11   12   10   38   39                                             
CONECT   12   11   14   13   40                                             
CONECT   13   12   41                                                       
CONECT   14   12   15   16   17                                             
CONECT   15   14   42   43   44                                             
CONECT   16   14   45   46   47                                             
CONECT   17   48   18   14    8                                             
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   18   21   49   50                                             
CONECT   21   20    7   23   22                                             
CONECT   22   21    3   51   52                                             
CONECT   23   21    2   24   53                                             
CONECT   24   23   54                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
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    1.6043    1.7226    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5531    1.1578    1.7404 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.4174    2.0936   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2461    2.6544   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8160    1.0779   -1.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990   -1.0497    0.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558   -1.1676   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    0.2673   -1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -0.1375   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738   -1.7637   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -2.6634   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5782   -4.1602   -2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -3.2027   -2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -5.1458   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -5.5018   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9552   -2.4675    0.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5970   -2.6723   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0669   -4.0486    0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -3.7578    2.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -4.4835    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5427   -5.2371    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1335   -2.6358    1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6858    0.2032    3.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -1.0804    2.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    1.5390    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832    2.2164    1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    1.3873    2.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9235    0.4168    0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  3  4  1  0
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  4  5  1  0
  5  7  1  0
 12 14  1  0
 17 48  1  1
  8  7  1  0
 14 15  1  6
 17 18  1  0
  8  9  1  6
 18 20  1  0
 14 16  1  0
 21 20  1  1
  5  6  1  0
 14 17  1  0
 12 13  1  0
  8 10  1  0
  7 32  1  1
  7 21  1  0
 21 23  1  0
  8 17  1  0
  3  2  1  0
 23  2  1  0
 21 22  1  0
  2  1  2  3
 23 24  1  0
 22  3  1  0
 18 19  2  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 10 36  1  0
 10 37  1  0
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 20 50  1  0
 22 51  1  0
 22 52  1  0
  3 27  1  6
  4 28  1  0
  4 29  1  0
  5 30  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
  6 31  1  0
 13 41  1  0
 23 53  1  1
  1 25  1  0
  1 26  1  0
 24 54  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(1S,4S,6S,9S,10S,11S,13S,15R)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-3-one

Traditional Name

(1S,4S,6S,9S,10S,11S,13S,15R)-6,11,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])[C@@]11C([H])([H])C(=O)[C@]3([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]1([H])[C@@]([H])(O[H])C2([H])[H]

InChI Identifier

InChI=1S/C20H30O4/c1-10-11-7-12(21)16-19(4)6-5-14(23)18(2,3)15(19)13(22)9-20(16,8-11)17(10)24/h11-12,14-17,21,23-24H,1,5-9H2,2-4H3/t11-,12+,14+,15-,16+,17-,19-,20+/m1/s1

InChI Key

WSZHSVSVZWABOB-ANWSMTEOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon tenuifolius	JEOL database	Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013)

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
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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
logP	1.25	ALOGPS
logP	1.08	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.78 m³·mol⁻¹	ChemAxon
Polarizability	36.66 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

29419188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71579052

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
Authors unspecified: Cancer Prevention Overview (PDQ(R)): Health Professional Version. 2002. [PubMed:26389451 ]
Authors unspecified: Spirituality in Cancer Care (PDQ(R)): Health Professional Version. 2002. [PubMed:26389436 ]
Authors unspecified: Oral Cavity, Oropharyngeal, Hypopharyngeal, and Laryngeal Cancer Prevention (PDQ(R)): Health Professional Version. 2002. [PubMed:26389416 ]
Authors unspecified: Adjustment to Cancer: Anxiety and Distress (PDQ(R)): Health Professional Version. 2002. [PubMed:26389397 ]
Ma B, Li X, Li J, Zhang Q, Liu Y, Yang X, Sun J, Yao D, Liu L, Liu X, Ying H: Quantitative analysis of tenuifolin concentrations in rat plasma and tissue using LCMS/MS: application to pharmacokinetic and tissue distribution study. J Pharm Biomed Anal. 2014 Jan;88:191-200. doi: 10.1016/j.jpba.2013.07.012. Epub 2013 Jul 23. [PubMed:24055855 ]
Yang, J. -H., et al. (2013). Yang, J. -H., et al, J. Nat. Prod. 76, 256 (2013). J. Nat. Prod..

Showing NP-Card for tenuifolin E (NP0043241)

MOL for NP0043241 (tenuifolin E)

3D MOL for NP0043241 (tenuifolin E)

3D SDF for NP0043241 (tenuifolin E)

3D-SDF for NP0043241 (tenuifolin E)

PDB for NP0043241 (tenuifolin E)

3D PDB for NP0043241 (tenuifolin E)

SMILES for NP0043241 (tenuifolin E)

INCHI for NP0043241 (tenuifolin E)

Structure for NP0043241 (tenuifolin E)

3D Structure for NP0043241 (tenuifolin E)