NP-MRD: Showing NP-Card for Lychnopholide (NP0044177)

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Record Information

Version

1.0

Created at

2021-11-12 23:54:29 UTC

Updated at

2021-11-26 17:46:17 UTC

NP-MRD ID

NP0044177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lychnopholide

Description

Lychnopholide belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Lychnopholide is found in Crateva nurvala, Eremanthus erythropappus, Lychnophora ericoides and Saussurea costus. It was first documented in 2012 (PMID: 22732730). Based on a literature review a significant number of articles have been published on Lychnopholide (PMID: 33359866) (PMID: 31988096) (PMID: 28814794) (PMID: 28349937) (PMID: 27324760) (PMID: 26577838).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

 26 28  0  0  1  0            999 V2000
   -0.9545   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  6  0  0  0
 16 25  1  0  0  0  0
 10 26  1  6  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    1.1739   -0.8877   -2.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.8205   -2.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1889   -1.2370   -3.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711   -1.6165   -4.4949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639   -1.1290   -2.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8952   -1.2932   -1.1961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0271   -1.4194   -0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4757   -0.8396    0.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524   -1.5082    1.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180    0.4273    1.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8463    0.9726    2.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846    1.9949    2.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    2.8928    3.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    1.6235    0.9575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3333    2.7495    0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652    0.3348    1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.3745   -0.0219 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4385   -0.0329   -0.0652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922   -0.8228    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029   -1.9524    0.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.3331    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469   -1.2658    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1989    0.8378   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993    1.8109   -0.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725   -0.3609   -1.1833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3298    1.3727    0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -1.2985   -3.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456   -0.5583   -2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3980   -2.3273   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7377   -2.2077   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917   -2.2489    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0756   -0.7870    2.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2198   -2.1060    0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4489    0.7358    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043    3.1370    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9722    3.6197    0.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738    2.4561   -0.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1870   -0.3497    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671    0.4427    1.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1118   -1.4601    0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012   -2.2901    0.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2534   -1.0367    1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8003   -1.0806    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2617    1.1090   -0.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    2.8221   -0.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528    2.0284    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    1.5955   -1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    0.6812   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 12  1  0
 12 13  2  0
 12 11  1  0
 11 10  2  0
 10 26  1  0
 10  8  1  0
  8  7  2  0
  7  6  1  0
  6 25  1  0
 25  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  8  9  1  0
 14 15  1  6
 25 17  1  0
 26 14  1  0
  5  6  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 23 44  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 17 40  1  1
 16 38  1  0
 16 39  1  0
 11 34  1  0
  7 30  1  0
  6 29  1  6
 25 48  1  6
  1 27  1  0
  1 28  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv1652311132100542D          

 26 28  0  0  1  0            999 V2000
   -0.9545   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  6  0  0  0
 16 25  1  0  0  0  0
 10 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17+,20-/m1/s1

> <INCHI_KEY>
QATUWZPYBIHFFR-UVXIKMMUSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.294377633629175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
3.0705717489999995

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.881129616141192

> <JCHEM_POLAR_SURFACE_AREA>
78.90000000000002

> <JCHEM_REFRACTIVITY>
96.22710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0      -1.782  -1.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.155  -2.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.376  -3.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.003  -4.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.281  -1.883   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.813  -2.044   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.560   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.025   0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.489   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.395   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.859   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.395   3.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.489   4.802   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.985   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.025   5.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.560   4.802   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.655   3.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.810   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.286   0.075   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.715   2.786   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.255   2.786   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.810   4.032   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.025   6.818   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.395  -0.476   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15   26                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   16                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2Z,4R,8R,9S,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17+,20-/m1/s1

InChI Key

QATUWZPYBIHFFR-UVXIKMMUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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
Crateva nurvala	LOTUS Database	35616633
Eremanthus erythropappus	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633
Saussurea costus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Fatty acyl
Dihydrofuran
Oxolane
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.24	ALOGPS
logP	3.07	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.23 m³·mol⁻¹	ChemAxon
Polarizability	36.29 Å³	ChemAxon
Number of Rings	3	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

C00012116

Chemspider ID

34521928

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49767028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bernardes ACFPF, Matosinhos RC, de Paula Michel Araujo MC, Barros CH, de Oliveira Aguiar Soares RD, Costa DC, Sachs D, Saude-Guimaraes DA: Sesquiterpene lactones from Lychnophora species: Antinociceptive, anti-inflammatory, and antioxidant pathways to treat acute gout. J Ethnopharmacol. 2021 Apr 6;269:113738. doi: 10.1016/j.jep.2020.113738. Epub 2020 Dec 24. [PubMed:33359866 ]
Branquinho RT, de Mello CGC, Oliveira MT, Reis LES, Vieira PMA, Saude-Guimaraes DA, Mosqueira VCF, de Lana M: Lychnopholide in Poly(d,l-Lactide)-Block-Polyethylene Glycol Nanocapsules Cures Infection with a Drug-Resistant Trypanosoma cruzi Strain at Acute and Chronic Phases. Antimicrob Agents Chemother. 2020 Mar 24;64(4). pii: AAC.01937-19. doi: 10.1128/AAC.01937-19. Print 2020 Mar 24. [PubMed:31988096 ]
Tupinamba Branquinho R, Pound-Lana G, Marques Milagre M, Saude-Guimaraes DA, Vilela JMC, Spangler Andrade M, de Lana M, Mosqueira VCF: Increased Body Exposure to New Anti-Trypanosomal Through Nanoencapsulation. Sci Rep. 2017 Aug 16;7(1):8429. doi: 10.1038/s41598-017-08469-x. [PubMed:28814794 ]
Branquinho RT, Roy J, Farah C, Garcia GM, Aimond F, Le Guennec JY, Saude-Guimaraes DA, Grabe-Guimaraes A, Mosqueira VC, de Lana M, Richard S: Biodegradable Polymeric Nanocapsules Prevent Cardiotoxicity of Anti-Trypanosomal Lychnopholide. Sci Rep. 2017 Mar 28;7:44998. doi: 10.1038/srep44998. [PubMed:28349937 ]
de Mello CG, Branquinho RT, Oliveira MT, Milagre MM, Saude-Guimaraes DA, Mosqueira VC, Lana Md: Efficacy of Lychnopholide Polymeric Nanocapsules after Oral and Intravenous Administration in Murine Experimental Chagas Disease. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5215-22. doi: 10.1128/AAC.00178-16. Print 2016 Sep. [PubMed:27324760 ]
Lachi-Silva L, Sousa JPB, Montanha MC, Sy SKB, Lopes JLC, Silva DB, Lopes NP, Diniz A, Kimura E: Rapid and efficient method for the quantification of lychnopholide in rat plasma by liquid chromatography-tandem mass spectrometry for pharmacokinetic application. Biomed Chromatogr. 2016 Jul;30(7):1092-1096. doi: 10.1002/bmc.3654. Epub 2016 Jan 3. [PubMed:26577838 ]
Lachi-Silva L, Sy SK, Voelkner A, de Sousa JP, Lopes JL, Silva DB, Lopes NP, Kimura E, Derendorf H, Diniz A: Simultaneous Characterization of Intravenous and Oral Pharmacokinetics of Lychnopholide in Rats by Transit Compartment Model. Planta Med. 2015 Aug;81(12-13):1121-7. doi: 10.1055/s-0035-1546214. Epub 2015 Jul 28. [PubMed:26218336 ]
Branquinho RT, Mosqueira VC, de Oliveira-Silva JC, Simoes-Silva MR, Saude-Guimaraes DA, de Lana M: Sesquiterpene lactone in nanostructured parenteral dosage form is efficacious in experimental Chagas disease. Antimicrob Agents Chemother. 2014;58(4):2067-75. doi: 10.1128/AAC.00617-13. Epub 2014 Jan 21. [PubMed:24449777 ]
Branquinho RT, Mosqueira VC, Kano EK, de Souza J, Dorim DD, Saude-Guimaraes DA, de Lana M: HPLC-DAD and UV-spectrophotometry for the determination of lychnopholide in nanocapsule dosage form: validation and application to release kinetic study. J Chromatogr Sci. 2014 Jan;52(1):19-26. doi: 10.1093/chromsci/bms199. Epub 2012 Dec 17. [PubMed:23247030 ]
de Souza MR, de Paula CA, Pereira de Resende ML, Grabe-Guimaraes A, de Souza Filho JD, Saude-Guimaraes DA: Pharmacological basis for use of Lychnophora trichocarpha in gouty arthritis: anti-hyperuricemic and anti-inflammatory effects of its extract, fraction and constituents. J Ethnopharmacol. 2012 Aug 1;142(3):845-50. doi: 10.1016/j.jep.2012.06.012. Epub 2012 Jun 23. [PubMed:22732730 ]
Ferdinand，Bohlmann，and，Christa，Zdero，and，Harold，Robinson，and，Robert，M.，King (1980). Caryophyllene derivatives and a heliangolide from Lychnophora species. Phytochemistry 19(11):2381-2385, 1980. DOI:10.1016/S0031-9422(00)91032-X. Phytochemistry.

Showing NP-Card for Lychnopholide (NP0044177)

MOL for NP0044177 (Lychnopholide)

3D MOL for NP0044177 (Lychnopholide)

3D SDF for NP0044177 (Lychnopholide)

3D-SDF for NP0044177 (Lychnopholide)

PDB for NP0044177 (Lychnopholide)

3D PDB for NP0044177 (Lychnopholide)

SMILES for NP0044177 (Lychnopholide)

INCHI for NP0044177 (Lychnopholide)

Structure for NP0044177 (Lychnopholide)

3D Structure for NP0044177 (Lychnopholide)