NP-MRD: Showing NP-Card for (1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione (NP0287973)

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Record Information

Version

2.0

Created at

2022-09-09 17:29:00 UTC

Updated at

2022-09-09 17:29:00 UTC

NP-MRD ID

NP0287973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione

Description

Longilactone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione is found in Eurycoma longifolia. (1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione was first documented in 2015 (PMID: 25914245). Based on a literature review a small amount of articles have been published on longilactone (PMID: 29975460) (PMID: 29154863) (PMID: 28839372).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219292D          

 26 29  0  0  1  0            999 V2000
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  1  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
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209    3.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1701    2.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0493    1.6455    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
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 13 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.1125    1.1772    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899    0.3226   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399   -0.7719   -0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133   -1.6267   -1.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485   -2.5388   -2.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2510   -1.3677   -1.5224 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6412   -2.6095   -1.5957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604   -0.6182   -0.2371 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5136   -1.3600    0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7638    0.6789   -0.3968 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4265    1.6895    0.6541 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0856    2.8730    0.3206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0352    1.9945    0.7349 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5812    2.5433   -0.4321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9686    2.3630   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753    2.9684   -1.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2460    1.2765    0.6032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2260    0.2846    0.1181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6965    0.5708   -1.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.1374    0.2013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7433   -1.8743   -0.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205   -1.4284   -0.2481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9802   -2.5400    0.4685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928   -0.2534   -0.1726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8689    0.7151    0.8797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7738    0.2782    2.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1226    0.6828    0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595    2.1114   -0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7901    1.3901    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771   -1.0194   -0.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -0.6947   -2.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1621   -3.2093   -2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8296   -1.7005    1.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181   -0.7793    1.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0672   -2.2857    0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231    1.1212   -1.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608    1.4128    1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    3.1465   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510    2.6239    1.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    1.7930    1.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.3964    0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -0.3618   -1.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658    0.8398   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5159    1.3297   -1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0177   -1.5111    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7479   -2.8271   -0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -1.7751   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666   -3.3269    0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669    0.3062   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694   -0.7019    2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816    0.4154    2.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    1.0147    2.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  8 24  1  0
 24 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 24 25  1  0
 25 26  1  1
 20 18  1  0
 25 17  1  0
 25 13  1  0
  8 10  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  1
 17 40  1  1
 13 39  1  1
 11 37  1  1
 12 38  1  0
 10 36  1  6
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  6 31  1  6
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 24 49  1  6
 22 47  1  6
 23 48  1  0
 20 45  1  1
 21 46  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END


  Mrv1652309092219292D          

 26 29  0  0  1  0            999 V2000
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8500   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  1  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
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6053    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6209    3.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1701    2.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0493    1.6455    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
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10  2  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 13 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0287973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2C(=O)O[C@@H]3[C@H](O)[C@H]4C(C)=CC(=O)[C@@H](O)[C@]4(C)[C@@H]([C@@H](O)[C@@H]1O)[C@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O7/c1-6-5-8(20)15(24)18(3)9(6)12(22)16-19(4)10(17(25)26-16)7(2)11(21)13(23)14(18)19/h5,7,9-16,21-24H,1-4H3/t7-,9-,10-,11-,12-,13+,14-,15-,16-,18+,19+/m1/s1

> <INCHI_KEY>
KBBRVTNGCNCUCX-LISBJPICSA-N

> <FORMULA>
C19H26O7

> <MOLECULAR_WEIGHT>
366.41

> <EXACT_MASS>
366.167853177

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.06479714124241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,7S,8R,9S,12S,13R,14R,15R,16R)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-5-ene-4,11-dione

> <JCHEM_LOGP>
-0.7460268383333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.503114675659358

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.80117465363428

> <JCHEM_PKA_STRONGEST_BASIC>
-3.265777353232762

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
89.87840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,7S,8R,9S,12S,13R,14R,15R,16R)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadec-5-ene-4,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.453  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.130   3.998   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.159   6.059   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.051   5.147   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.959   3.072   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24   13   17   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₇

Average Mass

366.4100 Da

Monoisotopic Mass

366.16785 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2C(=O)O[C@@H]3[C@H](O)[C@H]4C(C)=CC(=O)[C@@H](O)[C@]4(C)[C@@H]([C@@H](O)[C@@H]1O)[C@]23C

InChI Identifier

InChI=1S/C19H26O7/c1-6-5-8(20)15(24)18(3)9(6)12(22)16-19(4)10(17(25)26-16)7(2)11(21)13(23)14(18)19/h5,7,9-16,21-24H,1-4H3/t7-,9-,10-,11-,12-,13+,14-,15-,16-,18+,19+/m1/s1

InChI Key

KBBRVTNGCNCUCX-LISBJPICSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Cyclohexenone
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039531

Chemspider ID

58802192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14589371

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han YM, Jang M, Kim IS, Kim SH, Yoo HH: Simultaneous quantitation of six major quassinoids in Tongkat Ali dietary supplements by liquid chromatography with tandem mass spectrometry. J Sep Sci. 2015 Jul;38(13):2260-6. doi: 10.1002/jssc.201500207. Epub 2015 Jun 11. [PubMed:25914245 ]
Brauer P, Anielski P, Schwaiger S, Stuppner H, Tran TVA, Vollmer G, Zierau O, Thieme D, Keiler AM: In vitro metabolism of selected bioactive compounds of Eurycoma longifolia root extract to identify suitable markers in doping control. Drug Test Anal. 2019 Jan;11(1):86-94. doi: 10.1002/dta.2449. Epub 2018 Aug 9. [PubMed:29975460 ]
Mutschlechner B, Schwaiger S, Tran TVA, Stuppner H: Development of a selective HPLC-DAD/ELSD method for the qualitative and quantitative assessment of commercially available Eurycoma longifolia products and plant extracts. Fitoterapia. 2018 Jan;124:188-192. doi: 10.1016/j.fitote.2017.11.015. Epub 2017 Nov 14. [PubMed:29154863 ]
Tung NH, Uto T, Hai NT, Li G, Shoyama Y: Quassinoids from the Root of Eurycoma longifolia and Their Antiproliferative Activity on Human Cancer Cell Lines. Pharmacogn Mag. 2017 Jul-Sep;13(51):459-462. doi: 10.4103/pm.pm_353_16. Epub 2017 Jul 19. [PubMed:28839372 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione (NP0287973)

MOL for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

3D MOL for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

3D SDF for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

3D-SDF for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

PDB for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

3D PDB for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

SMILES for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

INCHI for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

Structure for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)

3D Structure for NP0287973 ((1r,2s,3s,7s,8r,9s,12s,13r,14r,15r,16r)-3,8,14,15-tetrahydroxy-2,6,13,16-tetramethyl-10-oxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadec-5-ene-4,11-dione)