NP-MRD: Showing NP-Card for Effusanin E (NP0074415)

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Record Information

Version

2.0

Created at

2022-04-28 19:37:18 UTC

Updated at

2022-04-28 19:37:18 UTC

NP-MRD ID

NP0074415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Effusanin E

Description

Effusanin 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. Effusanin E is found in Isodon effusus, Isodon longitubus, Isodon nervosus, Isodon oresbius, Isodon parvifolius, Isodon rubescens, Isodon rugosus, Isodon sinuolata and Isodon wikstroemioides. Effusanin E was first documented in 2004 (PMID: 15110700). Based on a literature review a small amount of articles have been published on Effusanin E (PMID: 16643043) (PMID: 25333664) (PMID: 23561188) (PMID: 19653147).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221372D          

 26 30  0  0  1  0            999 V2000
    7.3349   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9763    0.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1341    0.4235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8274   -0.4538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5193   -0.9618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3535   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206   -0.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3622    0.1026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7341    0.9050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6118    1.1973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8774    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    1.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4550    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -0.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821   -0.8796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5820   -1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244   -1.3877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8806   -2.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5371    1.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8120    1.3912    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 10 13  1  6  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  6  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 20 24  1  6  0  0  0
  9 24  1  6  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    4.7777    0.9435   -1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7043    0.5693   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    1.2700   -0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2055    2.3497   -1.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514    0.4614    0.4219 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6014   -0.1766    1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5677   -0.6660    0.2537 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9554   -1.7107   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705   -1.9330   -0.3512 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4004   -2.7128    0.7629 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8116   -0.6254   -0.3307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5992    0.1362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6407   -0.6316    1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194    0.3512    2.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365    1.2502    1.2752 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3317    2.2521    1.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5754    1.8010    0.5574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1906    2.9258   -0.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837    0.7315   -0.3377 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6419    0.8031   -0.4823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2279    2.1238    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0320    0.7891   -1.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458   -0.2693    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350   -1.6189    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561   -1.6774   -0.4336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9892   -2.9569   -0.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8248    1.8545   -1.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781    0.3439   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1070    0.6250    1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -0.9237    1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153   -1.0185    0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -2.7030   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -1.4289   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0962   -2.5060   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1237   -3.4028    0.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7763   -0.2524   -1.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -0.5641    2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374   -1.6116    2.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220    2.6992    1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2788    2.1380    1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4783    2.9253   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126    0.9338   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062    2.1219    1.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2950    2.1091   -0.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7678    2.9987   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4616   -0.2162   -2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962    1.5219   -2.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.8807   -2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7880    0.0730    1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277   -0.3491   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4489   -2.3785   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022   -2.0140    1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5482   -1.4828   -1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3616   -3.4172    0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 17 19  1  0
 15  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  5  3  1  6
 11 12  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  6
 26 54  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  1
 18 41  1  0
 19 42  1  6
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 11 36  1  6
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652304282221372D          

 26 30  0  0  1  0            999 V2000
    7.3349   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9763    0.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1341    0.4235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8274   -0.4538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5193   -0.9618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3535   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206   -0.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3622    0.1026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7341    0.9050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6118    1.1973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8774    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    1.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4550    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -0.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821   -0.8796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5820   -1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244   -1.3877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8806   -2.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5371    1.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8120    1.3912    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
 10 13  1  6  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  6  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 20 24  1  6  0  0  0
  9 24  1  6  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@H](O)[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12C[C@@H](C[C@@H](O)[C@@H]31)C(=C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9-10-6-11(21)13-18-8-26-20(25,19(13,7-10)15(9)23)16(24)14(18)17(2,3)5-4-12(18)22/h10-14,16,21-22,24-25H,1,4-8H2,2-3H3/t10-,11-,12+,13+,14-,16+,18+,19+,20-/m1/s1

> <INCHI_KEY>
HLVWYILWVYNUAJ-LBQBBFOZSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.80571668637032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,5S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
0.3847007340000008

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.70228175412204

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.588683965985881

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8604660459750697

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
92.0313

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.692  -1.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.187   0.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.022   1.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.450   0.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.878  -0.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.169  -1.795   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.860  -3.304   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.185  -1.268   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.143   0.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.837   1.689   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.475   2.235   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.971   3.693   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.811   2.838   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.183   1.173   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.571  -0.145   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.602   0.741   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.438   2.272   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.268  -0.087   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.825   0.451   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.753  -1.642   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.686  -2.929   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.259  -2.590   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.110  -3.874   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.118  -1.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.069   2.217   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.716   2.597   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   25   26                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   15                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   22                                                  
CONECT    9    8   10   16   24                                             
CONECT   10    9   11   13   14                                             
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14   10   15                                                       
CONECT   15   14    5                                                       
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8   23                                                  
CONECT   23   22                                                            
CONECT   24   20    9                                                       
CONECT   25    3                                                            
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

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(1S,2S,3R,5S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

Traditional Name

(1S,2S,3R,5S,8S,9S,10S,11R,15S)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@H](O)[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12C[C@@H](C[C@@H](O)[C@@H]31)C(=C)C2=O

InChI Identifier

InChI=1S/C20H28O6/c1-9-10-6-11(21)13-18-8-26-20(25,19(13,7-10)15(9)23)16(24)14(18)17(2,3)5-4-12(18)22/h10-14,16,21-22,24-25H,1,4-8H2,2-3H3/t10-,11-,12+,13+,14-,16+,18+,19+,20-/m1/s1

InChI Key

HLVWYILWVYNUAJ-LBQBBFOZSA-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
Isodon effusus	LOTUS Database	35616633
Isodon longitubus	LOTUS Database	35616633
Isodon nervosus	LOTUS Database	35616633
Isodon oresbius	Plant	KNApSAcK
Isodon parvifolius	Plant	KNApSAcK
Isodon rubescens	LOTUS Database	35616633
Isodon rugosus	LOTUS Database	35616633
Isodon sinuolata	Plant	KNApSAcK
Isodon wikstroemioides	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
Oxane
Cyclic alcohol
Hemiacetal
Ketone
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	0.01	ALOGPS
logP	0.38	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.03 m³·mol⁻¹	ChemAxon
Polarizability	37.81 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

C00035598

Chemspider ID

58802235

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24721137

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li LM, Li GY, Huang SX, Li SH, Zhou Y, Xiao WL, Lou LG, Ding LS, Sun HD: 7alpha,20-epoxy-ent-kauranoids from Isodon parvifolius. J Nat Prod. 2006 Apr;69(4):645-9. doi: 10.1021/np0600200. [PubMed:16643043 ]
Xiang W, Li RT, Wang ZY, Li SH, Zhao QS, Zhang HJ, Sun HD: ent-Kaurene diterpenoids from Isodon oresbius. Phytochemistry. 2004 Apr;65(8):1173-7. doi: 10.1016/j.phytochem.2004.02.022. [PubMed:15110700 ]
Zhuang M, Zhao M, Qiu H, Shi D, Wang J, Tian Y, Lin L, Deng W: Effusanin E suppresses nasopharyngeal carcinoma cell growth by inhibiting NF-kappaB and COX-2 signaling. PLoS One. 2014 Oct 21;9(10):e109951. doi: 10.1371/journal.pone.0109951. eCollection 2014. [PubMed:25333664 ]
Lin L, Zhu D, Zou L, Yang B, Zhao M: Antibacterial activity-guided purification and identification of a novel C-20 oxygenated ent-kaurane from Rabdosia serra (MAXIM.) HARA. Food Chem. 2013 Aug 15;139(1-4):902-9. doi: 10.1016/j.foodchem.2013.01.001. Epub 2013 Jan 12. [PubMed:23561188 ]
Bai N, He K, Zhou Z, Tsai ML, Zhang L, Quan Z, Shao X, Pan MH, Ho CT: Ent-kaurane diterpenoids from Rabdosia rubescens and their cytotoxic effects on human cancer cell lines. Planta Med. 2010 Feb;76(2):140-5. doi: 10.1055/s-0029-1186002. Epub 2009 Aug 3. [PubMed:19653147 ]

Showing NP-Card for Effusanin E (NP0074415)

MOL for NP0074415 (Effusanin E)

3D MOL for NP0074415 (Effusanin E)

3D SDF for NP0074415 (Effusanin E)

3D-SDF for NP0074415 (Effusanin E)

PDB for NP0074415 (Effusanin E)

3D PDB for NP0074415 (Effusanin E)

SMILES for NP0074415 (Effusanin E)

INCHI for NP0074415 (Effusanin E)

Structure for NP0074415 (Effusanin E)

3D Structure for NP0074415 (Effusanin E)