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Showing NP-Card for (5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide (NP0353072)

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Record Information
Version2.0
Created at2026-02-17 09:01:26 UTC
Updated at2026-02-17 12:01:53 UTC
NP-MRD IDNP0353072
Natural Product DOIhttps://doi.org/10.57994/7414
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide
Description (5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide was first documented in 2019 (PMID: 31710213).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)


  Mrv2104 03182306142D          

 24 26  0  0  1  0            999 V2000
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.5474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7376    2.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 10  1  0  0  0  0
 15 16  1  1  0  0  0
 17  7  1  0  0  0  0
 17  2  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
Download

3D MOL for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)

Download
3D SDF for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)

  Mrv2104 03182306142D          

 24 26  0  0  1  0            999 V2000
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.5474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7376    2.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 10  1  0  0  0  0
 15 16  1  1  0  0  0
 17  7  1  0  0  0  0
 17  2  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0353072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=C)[C@H](\C=C\C3=CC(=O)O[C@H]3O)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h7-8,12,15-16,18,22H,1,5-6,9-11H2,2-4H3/b8-7+/t15-,16-,18+,20+/m0/s1

> <INCHI_KEY>
KJUPGEKTXQYTSU-LKEKRHCZSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

$$$$

Download
3D-SDF for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)
Download
PDB for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)
HEADER    PROTEIN                                 18-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-23         0                                  
HETATM    1  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.580   4.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.104   6.220   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.009   7.466   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.564   6.220   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.088   4.755   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.377   4.279   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17    7    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

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3D PDB for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)
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SMILES for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)
[H][C@@]12CCC(=C)[C@H](\C=C\C3=CC(=O)O[C@H]3O)[C@@]1(C)CCCC2(C)C
Download
INCHI for NP0353072 ((5S,9S,10S,16R,11E)-16-Hydroxylabda-8(17),11,13-trien-15,16-olide)
InChI=1S/C20H28O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h7-8,12,15-16,18,22H,1,5-6,9-11H2,2-4H3/b8-7+/t15-,16-,18+,20+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(=C)[C@H](\C=C\C3=CC(=O)O[C@H]3O)[C@@]1(C)CCCC2(C)C
InChI Identifier
InChI=1S/C20H28O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h7-8,12,15-16,18,22H,1,5-6,9-11H2,2-4H3/b8-7+/t15-,16-,18+,20+/m0/s1
InChI KeyKJUPGEKTXQYTSU-LKEKRHCZSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500.0, Methanol-d4, simulated)epoynton@sfu.caNot AvailableNot Available2026-02-17View Spectrum
1D NMR13C NMR Spectrum (1D, 125.0, Methanol-d4, simulated)epoynton@sfu.caNot AvailableNot Available2026-02-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Amomum villosum var. xanthioides
      Not Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
External LinksNot Available
References
General References
  1. DOI: 10.1021/acs.jnatprod.9b00283
  2. PMID: 31710213