NP-MRD: Showing NP-Card for Lobatin B (NP0058671)

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Record Information

Version

2.0

Created at

2022-04-28 04:00:23 UTC

Updated at

2022-04-28 04:00:23 UTC

NP-MRD ID

NP0058671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lobatin B

Description

LOBATIN B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Lobatin B is found in Neurolaena lobata and Neurolaena oaxacana. Lobatin B was first documented in 2002 (PMID: 12116880). Based on a literature review a small amount of articles have been published on LOBATIN B (PMID: 25444930) (PMID: 23747054).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206002D          

 27 29  0  0  1  0            999 V2000
   -1.5930    3.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439    1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234    1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    1.4242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7266    2.1779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5551    2.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0580    3.5369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8785    3.6231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0500    4.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    4.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    5.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775    4.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    4.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    3.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    2.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    2.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471    2.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  6  0  0  0
 15 16  2  0  0  0  0
  9 17  1  6  0  0  0
 17 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
 21 23  1  0  0  0  0
  8 24  1  1  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
  7 26  1  1  0  0  0
  2 27  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    0.0951    3.2893   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    2.3931    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.5690    1.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2073    3.4278    2.5244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097    1.6158    2.1719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    0.5738    1.1803 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2398    0.3713    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7394   -0.8003    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -1.3100    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -1.6305   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0619   -2.6673   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -2.6617   -1.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3976   -3.6322   -2.4199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4858   -1.2264   -1.6930 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5814   -0.4952   -2.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -1.3178   -0.2495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2020   -0.6463   -1.8112 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0674   -0.0018   -3.0595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493    0.3686   -0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9411   -0.2121    0.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2466    0.2237    0.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6435    1.1634   -0.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -0.3520    1.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447    0.3029    1.3200 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4148   -0.3979    2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2390    0.1639    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141    1.0100   -0.0464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2407    4.2392   -0.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    3.1200   -1.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403   -0.2648    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9547    1.0992    1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0826   -2.4153    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7639   -1.0480    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4927   -0.8195    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026   -3.3274   -0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4359   -0.3145   -1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2839    0.3962   -2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896   -1.1767   -3.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6203   -1.3723   -1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    0.9600   -2.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6393    1.1592   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2681   -1.4412    1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242   -0.2415    2.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5201    1.3593    1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3512   -1.4884    2.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0359   -0.1514    3.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4651   -0.0904    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3357    0.3540    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1947   -0.8626   -0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447    0.9349   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749    1.2709   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 24 23  1  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  1  0
 19 27  1  0
 27  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
  2 27  1  0
 16 10  1  0
 25 45  1  0
 25 46  1  0
 25 47  1  0
 24 44  1  1
 26 48  1  0
 26 49  1  0
 26 50  1  0
 23 42  1  0
 23 43  1  0
 19 41  1  6
 27 51  1  6
  6 30  1  1
  1 28  1  0
  1 29  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 11 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  6
 18 40  1  0
M  END


  Mrv1652304282206002D          

 27 29  0  0  1  0            999 V2000
   -1.5930    3.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9285    2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7570    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439    1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3234    1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910    1.4242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7266    2.1779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5551    2.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0580    3.5369    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8785    3.6231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0500    4.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356    4.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493    5.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775    4.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0845    4.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    3.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    2.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    2.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    2.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5471    2.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  6  0  0  0
 15 16  2  0  0  0  0
  9 17  1  6  0  0  0
 17 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
 21 23  1  0  0  0  0
  8 24  1  1  0  0  0
  7 25  1  0  0  0  0
  3 25  1  0  0  0  0
  7 26  1  1  0  0  0
  2 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)/C2=CC(=O)[C@](C)(O2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O7/c1-9(2)6-15(22)26-17-16-11(4)19(24)25-13(16)7-10(3)12-8-14(21)20(5,27-12)18(17)23/h7-9,13,16-18,23H,4,6H2,1-3,5H3/b10-7-/t13-,16+,17+,18-,20+/m1/s1

> <INCHI_KEY>
JXMKTEYFXIBRKC-BXRXTLJPSA-N

> <FORMULA>
C20H24O7

> <MOLECULAR_WEIGHT>
376.405

> <EXACT_MASS>
376.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.141308716267076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8S,9S,10R,11R)-10-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 3-methylbutanoate

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
2.040588852

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.812801629239011

> <JCHEM_PKA_STRONGEST_BASIC>
-3.755480567370854

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
96.4224

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8S,9S,10R,11R)-10-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 3-methylbutanoate

> <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      -2.974   5.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.600   4.586   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.280   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.135   2.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.604   1.889   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.284   0.382   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.730   2.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.356   4.065   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.036   5.572   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.108   6.602   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.640   6.763   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.960   8.270   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.626   9.040   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.465  10.571   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.518   8.009   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.024   8.329   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.370   6.342   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.703   5.572   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.703   4.032   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.037   6.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.371   5.572   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.705   6.342   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.371   4.032   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.888   3.904   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.222   3.370   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.874   1.628   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.131   4.747   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   25   26                                             
CONECT    8    7    9   24                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10    1   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16                                                  
CONECT   16   15                                                            
CONECT   17    9   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    8                                                            
CONECT   25    7    3                                                       
CONECT   26    7                                                            
CONECT   27    2                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₇

Average Mass

376.4050 Da

Monoisotopic Mass

376.15220 Da

IUPAC Name

(2Z,4R,8S,9S,10R,11R)-10-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 3-methylbutanoate

Traditional Name

(2Z,4R,8S,9S,10R,11R)-10-hydroxy-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)\C=C(C)/C2=CC(=O)[C@](C)(O2)[C@@H]1O

InChI Identifier

InChI=1S/C20H24O7/c1-9(2)6-15(22)26-17-16-11(4)19(24)25-13(16)7-10(3)12-8-14(21)20(5,27-12)18(17)23/h7-9,13,16-18,23H,4,6H2,1-3,5H3/b10-7-/t13-,16+,17+,18-,20+/m1/s1

InChI Key

JXMKTEYFXIBRKC-BXRXTLJPSA-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
Neurolaena lobata	Plant	KNApSAcK
Neurolaena oaxacana	Plant	KNApSAcK

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
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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	1.37	ALOGPS
logP	2.04	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.42 m³·mol⁻¹	ChemAxon
Polarizability	38.14 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

C00012090

Chemspider ID

4945003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440752

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kiss I, Unger C, Huu CN, Atanasov AG, Kramer N, Chatruphonprasert W, Brenner S, McKinnon R, Peschel A, Vasas A, Lajter I, Kain R, Saiko P, Szekeres T, Kenner L, Hassler MR, Diaz R, Frisch R, Dirsch VM, Jager W, de Martin R, Bochkov VN, Passreiter CM, Peter-Vorosmarty B, Mader RM, Grusch M, Dolznig H, Kopp B, Zupko I, Hohmann J, Krupitza G: Lobatin B inhibits NPM/ALK and NF-kappaB attenuating anaplastic-large-cell-lymphomagenesis and lymphendothelial tumour intravasation. Cancer Lett. 2015 Jan 28;356(2 Pt B):994-1006. doi: 10.1016/j.canlet.2014.11.019. Epub 2014 Nov 15. [PubMed:25444930 ]
Walshe-Roussel B, Choueiri C, Saleem A, Asim M, Caal F, Cal V, Rojas MO, Pesek T, Durst T, Arnason JT: Potent anti-inflammatory activity of sesquiterpene lactones from Neurolaena lobata (L.) R. Br. ex Cass., a Q'eqchi' Maya traditional medicine. Phytochemistry. 2013 Aug;92:122-7. doi: 10.1016/j.phytochem.2013.05.004. Epub 2013 Jun 5. [PubMed:23747054 ]
Blair S, Mesa J, Correa A, Carmona-Fonseca J, Granados H, Saez J: Antimalarial activity of neurolenin B and derivates of Eupatorium inulaefolium (Asteraceae). Pharmazie. 2002 Jun;57(6):413-5. [PubMed:12116880 ]

Showing NP-Card for Lobatin B (NP0058671)

MOL for NP0058671 (Lobatin B)

3D MOL for NP0058671 (Lobatin B)

3D SDF for NP0058671 (Lobatin B)

3D-SDF for NP0058671 (Lobatin B)

PDB for NP0058671 (Lobatin B)

3D PDB for NP0058671 (Lobatin B)

SMILES for NP0058671 (Lobatin B)

INCHI for NP0058671 (Lobatin B)

Structure for NP0058671 (Lobatin B)

3D Structure for NP0058671 (Lobatin B)