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Showing NP-Card for Glabrolide (NP0334930)

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Record Information
Version2.0
Created at2024-09-10 23:07:24 UTC
Updated at2024-09-10 23:07:24 UTC
NP-MRD IDNP0334930
Secondary Accession NumbersNone
Natural Product Identification
Common NameGlabrolide
DescriptionGlabrolide belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Glabrolide was first documented in 2020 (PMID: 30767744). Based on a literature review very few articles have been published on Glabrolide (PMID: 33988079).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334930 (Glabrolide)


  Mrv2104 05262301392D          

 34 39  0  0  0  0            999 V2000
    0.3573   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010    1.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167   -3.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552   -3.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576    2.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    3.0818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 22  1  0  0  0  0
  1 34  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 29  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 32  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 33  1  0  0  0  0
 18 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
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
Download

3D MOL for NP0334930 (Glabrolide)

Download
3D SDF for NP0334930 (Glabrolide)

  Mrv2104 05262301392D          

 34 39  0  0  0  0            999 V2000
    0.3573   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0724    0.4379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010    1.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -0.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5010   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0710   -1.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010   -1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5010   -2.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -2.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3167   -3.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7860   -2.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2552   -3.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576    2.1634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702    2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    3.0818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698   -1.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 22  1  0  0  0  0
  1 34  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 29  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 24  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 32  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 33  1  0  0  0  0
 18 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
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC1=O)C1(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2

> <INCHI_IDENTIFIER>
InChI=1/C30H44O4/c1-25(2)20-8-11-30(7)23(28(20,5)10-9-21(25)32)19(31)14-17-18-15-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h14,18,20-23,32H,8-13,15-16H2,1-7H3

> <INCHI_KEY>
SSHDNSCEQSPWIM-UHFFFAOYNA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.12687014494138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-16,22-dione

> <JCHEM_LOGP>
5.464988094000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.48941909028516

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.708214370882224

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351054164934165

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
132.29179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-16,22-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0334930 (Glabrolide)
Download
PDB for NP0334930 (Glabrolide)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       0.667  -2.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667  -3.802   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -4.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.002  -3.802   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002  -2.262   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.002  -0.722   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -1.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667   0.047   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.002   0.817   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.667   0.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.999   0.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.334   0.817   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334   2.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.669   3.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.657   4.308   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.000   2.357   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.000   0.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.000  -0.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.669   0.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.669  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.334  -2.262   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.999  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.999  -3.032   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.334  -1.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.669  -2.262   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.669  -3.802   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.000  -4.572   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.325  -5.753   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.334  -4.572   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.343  -5.753   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.161   4.038   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.678   4.308   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.204   5.753   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.437  -3.597   0.000  0.00  0.00           C+0
CONECT    1    2    7   22   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6    7   24                                             
CONECT    6    5                                                            
CONECT    7    1    5    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   19   33                                                  
CONECT   18   19                                                            
CONECT   19   12   17   18   20                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    1   11   21   23                                             
CONECT   23   22                                                            
CONECT   24    5   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29    4   26   28   30                                             
CONECT   30   29                                                            
CONECT   31   32                                                            
CONECT   32   14   31   33                                                  
CONECT   33   17   32                                                       
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

Download
3D PDB for NP0334930 (Glabrolide)
Download
SMILES for NP0334930 (Glabrolide)
CC12CC(OC1=O)C1(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2
Download
INCHI for NP0334930 (Glabrolide)
InChI=1/C30H44O4/c1-25(2)20-8-11-30(7)23(28(20,5)10-9-21(25)32)19(31)14-17-18-15-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h14,18,20-23,32H,8-13,15-16H2,1-7H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC30H44O4
Average Mass468.6780 Da
Monoisotopic Mass468.32396 Da
IUPAC Name11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-16,22-dione
Traditional Name11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-16,22-dione
CAS Registry NumberNot Available
SMILES
CC12CC(OC1=O)C1(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2
InChI Identifier
InChI=1/C30H44O4/c1-25(2)20-8-11-30(7)23(28(20,5)10-9-21(25)32)19(31)14-17-18-15-26(3)16-22(34-24(26)33)27(18,4)12-13-29(17,30)6/h14,18,20-23,32H,8-13,15-16H2,1-7H3
InChI KeySSHDNSCEQSPWIM-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTriterpenoids  
Direct ParentTriterpenoids  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Caprolactone
    • 

  • Cyclohexenone
    • 

  • Oxepane
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP5.46ChemAxon
pKa (Strongest Acidic)17.71ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity132.29 m³·mol⁻¹ChemAxon
Polarizability54.13 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Joshi C, Chaudhari A, Joshi C, Joshi M, Bagatharia S: Repurposing of the herbal formulations: molecular docking and molecular dynamics simulation studies to validate the efficacy of phytocompounds against SARS-CoV-2 proteins. J Biomol Struct Dyn. 2021 May 14:1-15. doi: 10.1080/07391102.2021.1922095. [PubMed:33988079  ] 
  2. Arif N, Subhani A, Hussain W, Rasool N: In Silico Inhibition of BACE-1 by Selective Phytochemicals as Novel Potential Inhibitors: Molecular Docking and DFT Studies. Curr Drug Discov Technol. 2020;17(3):397-411. doi: 10.2174/1570163816666190214161825. [PubMed:30767744  ]