NP-MRD: Showing NP-Card for tenuifolin L (NP0043248)

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Record Information

Version

1.0

Created at

2021-06-21 00:42:40 UTC

Updated at

2021-06-30 00:18:49 UTC

NP-MRD ID

NP0043248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tenuifolin L

Provided By

JEOL Database JEOL Logo

Description

Tenuifolin L 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 L is found in Isodon tenuifolius. It was first documented in 2007 (PMID: 17927264). Based on a literature review very few articles have been published on Tenuifolin L (PMID: 25705699) (PMID: 24702811) (PMID: 19754130) (PMID: 26495659).

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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    2.3338    0.9146   -2.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344    1.4307   -3.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    0.2029   -1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971   -0.4937    0.1776 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4189   -1.5482    1.1688 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6066   -0.9352    2.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -1.9653    0.5878 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7553   -0.8967    0.6722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616   -3.1657    1.2989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5616   -4.3985    1.3127 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4280   -4.8510   -0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545   -4.1190    1.9180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2816   -4.0121    3.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -5.3414    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.8647    1.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8840   -2.5061    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -2.7513    2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5550   -2.4272   -0.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5893    1.7517    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9522    3.0229    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    2.0439    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.9260    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    1.0933   -4.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    1.0412   -3.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261    2.5235   -3.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8048   -0.9518   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -1.4181    3.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -1.0049    3.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1133    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.2241   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783   -0.5595   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3977   -3.4029    0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -2.8966    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528   -5.2061    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3011   -5.1683   -0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -3.3208    3.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -4.9850    3.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -3.7149    3.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0172   -5.4502    0.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7183   -5.2582    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -6.2713    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -3.1858    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509   -1.5679    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308   -1.8290   -1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0  0  0  0
 27 63  1  6  0  0  0
 27 28  1  0  0  0  0
 11 12  1  0  0  0  0
 28 30  1  0  0  0  0
  9  4  1  0  0  0  0
 30  7  1  0  0  0  0
  7  5  1  6  0  0  0
  4  5  1  0  0  0  0
 16  7  1  0  0  0  0
 12 13  1  0  0  0  0
 24 27  1  0  0  0  0
 13 15  2  0  0  0  0
 17 19  1  0  0  0  0
 13 14  1  0  0  0  0
 17 27  1  0  0  0  0
 17 18  1  1  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 28 29  2  0  0  0  0
 21 19  1  0  0  0  0
 30 31  1  0  0  0  0
 16 11  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
 16 47  1  6  0  0  0
  8  9  1  0  0  0  0
 24 25  1  1  0  0  0
  9 10  1  0  0  0  0
 24 26  1  0  0  0  0
 10 11  1  0  0  0  0
  4  3  1  0  0  0  0
 22 24  1  0  0  0  0
  3  2  1  0  0  0  0
 22 23  1  0  0  0  0
  2  1  1  0  0  0  0
 21 53  1  0  0  0  0
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  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(=O)[C@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])[C@@]2(C([H])([H])[H])[C@]2([H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])[C@]12C(=O)[C@@]3([H])C([H])([H])OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O8/c1-10(24)31-13-6-11-8-23(19(28)12(11)9-30-5)17(13)22(4)15(26)7-14(25)21(2,3)18(22)16(27)20(23)29/h11-15,17-18,20,25-26,29H,6-9H2,1-5H3/t11-,12+,13+,14+,15+,17+,18-,20+,22+,23+/m1/s1

> <INCHI_KEY>
MDENNICXVBURAU-AZABVYRPSA-N

> <FORMULA>
C23H34O8

> <MOLECULAR_WEIGHT>
438.517

> <EXACT_MASS>
438.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.5655884750488

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8S,9S,10S,11S,13S,14R)-2,6,8-trihydroxy-14-(methoxymethyl)-5,5,9-trimethyl-3,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
-0.12564138666666713

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.294720859804045

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.735194969323832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.96939892251652

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
108.85079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8S,9S,10S,11S,13S,14R)-2,6,8-trihydroxy-14-(methoxymethyl)-5,5,9-trimethyl-3,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
   -4.3835    4.2277   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    3.7398    0.0012 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8539    1.9563    0.9551 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6792    2.0493    0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    0.9221    0.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3230    1.3445   -1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    0.9146   -2.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344    1.4307   -3.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    0.2029   -1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6971   -0.4937    0.1776 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4189   -1.5482    1.1688 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8175   -1.9653    0.5878 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5616   -4.3985    1.3127 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4280   -4.8510   -0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545   -4.1190    1.9180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2816   -4.0121    3.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -5.3414    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.8647    1.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8840   -2.5061    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6973    0.3883    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308    2.7691    1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    3.0229    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    2.0439    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.9260    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1984    1.0412   -3.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8048   -0.9518   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -1.4181    3.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -1.0049    3.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1133    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.2241   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783   -0.5595   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7695   -2.8966    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5567   -4.9850    3.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -3.7149    3.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0172   -5.4502    0.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7131   -6.2713    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -3.1858    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509   -1.5679    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308   -1.8290   -1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 27 63  1  6
 27 28  1  0
 11 12  1  0
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  9  4  1  0
 30  7  1  0
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 16  7  1  0
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 13 15  2  0
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  2  1  1  0
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  1 32  1  0
  1 33  1  0
  1 34  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      -4.383   4.228  -0.019  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.048   3.740   0.001  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.973   2.388  -0.449  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.514   1.947  -0.439  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.431   0.474  -0.777  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.789  -0.005  -1.848  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.859  -0.353   0.378  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.220   0.594   1.533  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.854   1.956   0.955  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.679   2.049   0.882  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.369   0.922   0.080  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.323   1.345  -1.310  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.334   0.915  -2.116  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.134   1.431  -3.507  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.265   0.203  -1.764  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.697  -0.494   0.178  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.419  -1.548   1.169  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.607  -0.935   2.574  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.817  -1.965   0.588  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.755  -0.897   0.672  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.462  -3.166   1.299  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.562  -4.399   1.313  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.428  -4.851  -0.038  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.155  -4.119   1.918  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.282  -4.012   3.451  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.239  -5.341   1.637  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.561  -2.865   1.197  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.884  -2.506   1.541  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.418  -2.751   2.620  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.597  -1.689   0.475  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.555  -2.427  -0.744  0.00  0.00           O+0
HETATM   32  H   UNK     0      -4.378   5.261   0.336  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.782   4.210  -1.038  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.018   3.633   0.644  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.589   1.752   0.197  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.374   2.320  -1.468  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.935   2.550  -1.146  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.293   0.557   1.761  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.697   0.388   2.466  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.231   2.769   1.585  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.952   3.023   0.455  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.064   2.044   1.909  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.412   0.926   0.392  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.960   1.093  -4.140  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.198   1.041  -3.915  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.126   2.523  -3.499  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.805  -0.952  -0.818  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.403  -1.418   3.142  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.702  -1.005   3.183  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.905   0.113   2.532  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.703  -2.224  -0.473  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.878  -0.560  -0.244  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.398  -3.403   0.775  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.769  -2.897   2.315  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.053  -5.206   1.869  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.301  -5.168  -0.329  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.058  -3.321   3.776  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.557  -4.985   3.878  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.346  -3.715   3.930  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.017  -5.450   0.569  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.718  -5.258   2.163  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.713  -6.271   1.972  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.502  -3.186   0.145  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.651  -1.568   0.749  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.831  -1.829  -1.472  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3    4    2   35   36                                             
CONECT    4    9    5    3   37                                             
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7   30    5   16    8                                             
CONECT    8    7    9   38   39                                             
CONECT    9    4    8   10   40                                             
CONECT   10    9   11   41   42                                             
CONECT   11   12   16   10   43                                             
CONECT   12   11   13                                                       
CONECT   13   12   15   14                                                  
CONECT   14   13   44   45   46                                             
CONECT   15   13                                                            
CONECT   16   17    7   11   47                                             
CONECT   17   16   19   27   18                                             
CONECT   18   17   48   49   50                                             
CONECT   19   17   20   21   51                                             
CONECT   20   19   52                                                       
CONECT   21   22   19   53   54                                             
CONECT   22   21   24   23   55                                             
CONECT   23   22   56                                                       
CONECT   24   27   25   26   22                                             
CONECT   25   24   57   58   59                                             
CONECT   26   24   60   61   62                                             
CONECT   27   63   28   24   17                                             
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28    7   31   64                                             
CONECT   31   30   65                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    8                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   30                                                            
CONECT   65   31                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
   -4.3835    4.2277   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    3.7398    0.0012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728    2.3879   -0.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5135    1.9468   -0.4393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4309    0.4744   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7889   -0.0053   -1.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8590   -0.3529    0.3784 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2203    0.5940    1.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539    1.9563    0.9551 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6792    2.0493    0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685    0.9221    0.0795 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3230    1.3445   -1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    0.9146   -2.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1344    1.4307   -3.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2653    0.2029   -1.7641 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4189   -1.5482    1.1688 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6066   -0.9352    2.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -1.9653    0.5878 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5616   -4.3985    1.3127 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4280   -4.8510   -0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545   -4.1190    1.9180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2816   -4.0121    3.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387   -5.3414    1.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -2.8647    1.1972 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8840   -2.5061    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4181   -2.7513    2.6205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -1.6892    0.4754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5550   -2.4272   -0.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3777    5.2615    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7817    4.2102   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182    3.6329    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    1.7517    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737    2.3200   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9354    2.5495   -1.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    0.5569    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973    0.3883    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308    2.7691    1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9522    3.0229    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640    2.0439    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4122    0.9260    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    1.0933   -4.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    1.0412   -3.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261    2.5235   -3.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8048   -0.9518   -0.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -1.4181    3.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -1.0049    3.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051    0.1133    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -2.2241   -0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8783   -0.5595   -0.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3977   -3.4029    0.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -2.8966    2.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528   -5.2061    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3011   -5.1683   -0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -3.3208    3.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567   -4.9850    3.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -3.7149    3.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0172   -5.4502    0.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7183   -5.2582    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131   -6.2713    1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -3.1858    0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509   -1.5679    0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308   -1.8290   -1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 27 63  1  6
 27 28  1  0
 11 12  1  0
 28 30  1  0
  9  4  1  0
 30  7  1  0
  7  5  1  6
  4  5  1  0
 16  7  1  0
 12 13  1  0
 24 27  1  0
 13 15  2  0
 17 19  1  0
 13 14  1  0
 17 27  1  0
 17 18  1  1
 19 20  1  0
 21 22  1  0
 28 29  2  0
 21 19  1  0
 30 31  1  0
 16 11  1  0
  5  6  2  0
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  8  9  1  0
 24 25  1  1
  9 10  1  0
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 10 11  1  0
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  3  2  1  0
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  2  1  1  0
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 21 54  1  0
 22 55  1  1
 19 51  1  6
 30 64  1  1
  8 38  1  0
  8 39  1  0
  9 40  1  1
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 23 56  1  0
  4 37  1  6
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 18 48  1  0
 18 49  1  0
 18 50  1  0
 20 52  1  0
 31 65  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 26 62  1  0
  3 35  1  0
  3 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄O₈

Average Mass

438.5170 Da

Monoisotopic Mass

438.22537 Da

IUPAC Name

(1R,2R,4R,6S,8S,9S,10S,11S,13S,14R)-2,6,8-trihydroxy-14-(methoxymethyl)-5,5,9-trimethyl-3,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate

Traditional Name

(1R,2R,4R,6S,8S,9S,10S,11S,13S,14R)-2,6,8-trihydroxy-14-(methoxymethyl)-5,5,9-trimethyl-3,15-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-11-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(=O)[C@]2([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])[C@@]2(C([H])([H])[H])[C@]2([H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]3([H])C([H])([H])[C@]12C(=O)[C@@]3([H])C([H])([H])OC([H])([H])[H]

InChI Identifier

InChI=1S/C23H34O8/c1-10(24)31-13-6-11-8-23(19(28)12(11)9-30-5)17(13)22(4)15(26)7-14(25)21(2,3)18(22)16(27)20(23)29/h11-15,17-18,20,25-26,29H,6-9H2,1-5H3/t11-,12+,13+,14+,15+,17+,18-,20+,22+,23+/m1/s1

InChI Key

MDENNICXVBURAU-AZABVYRPSA-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
Carboxylic acid ester
Ketone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
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	0.68	ALOGPS
logP	-0.13	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.85 m³·mol⁻¹	ChemAxon
Polarizability	45.57 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

29420450

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71579128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wen L, Xia N, Tang P, Hong Y, Wang Z, Liu Y, Liu Y, Liu J, Li X: The gastrointestinal irritation of polygala saponins and its potential mechanism in vitro and in vivo. Biomed Res Int. 2015;2015:918048. doi: 10.1155/2015/918048. Epub 2015 Feb 1. [PubMed:25705699 ]
Zhou YH, Zhang SY, Guo Q, Chai XY, Jiang Y, Tu PF: Chemical investigation of the roots of Polygala sibirica L. Chin J Nat Med. 2014 Mar;12(3):225-8. doi: 10.1016/S1875-5364(14)60038-8. [PubMed:24702811 ]
Diome C, Mitaine-Offer AC, Miyamoto T, Delaude C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA: Saponins from the roots of Nylandtia spinosa. J Nat Prod. 2007 Oct;70(10):1680-2. doi: 10.1021/np0703186. Epub 2007 Oct 11. [PubMed:17927264 ]
Lin RJ, Cheng MJ, Huang JC, Lo WL, Yeh YT, Yen CM, Lu CM, Chen CY: Cytotoxic compounds from the stems of Cinnamomum tenuifolium. J Nat Prod. 2009 Oct;72(10):1816-24. doi: 10.1021/np900225p. [PubMed:19754130 ]
Huang LH, Wang J, Zhang L, Luo SL, Chen C, Du J: [Intestinal Absorption Characteristics and Mechanism of Polygala tenuifolia Hydrolysate in Rats]. Zhong Yao Cai. 2015 Mar;38(3):556-61. [PubMed:26495659 ]
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 L (NP0043248)

MOL for NP0043248 (tenuifolin L)

3D MOL for NP0043248 (tenuifolin L)

3D SDF for NP0043248 (tenuifolin L)

3D-SDF for NP0043248 (tenuifolin L)

PDB for NP0043248 (tenuifolin L)

3D PDB for NP0043248 (tenuifolin L)

SMILES for NP0043248 (tenuifolin L)

INCHI for NP0043248 (tenuifolin L)

Structure for NP0043248 (tenuifolin L)

3D Structure for NP0043248 (tenuifolin L)