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Showing NP-Card for Ajugarin IX (NP0332140)

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Record Information
Version2.0
Created at2023-11-24 00:00:30 UTC
Updated at2026-02-26 20:52:34 UTC
NP-MRD IDNP0332140
Natural Product DOIhttps://doi.org/10.57994/1297
Secondary Accession NumbersNone
Natural Product Identification
Common NameAjugarin IX
DescriptionAjugarin IX belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Ajugarin IX was first documented in 2023 (PMID: 37972998). Based on a literature review very few articles have been published on Ajugarin IX.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0332140 (Ajugarin IX)


  Mrv2104 11242300002D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    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  2  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.1387    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 O   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
    0.0000   -0.0000    0.0000 C   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
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297    1.2798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675    1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 26  1  6  0  0  0
 16 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 30 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
Download

3D MOL for NP0332140 (Ajugarin IX)

Download
3D SDF for NP0332140 (Ajugarin IX)

  Mrv2104 11242300002D          

 34 36  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    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  2  0  0  0  0  0  0  0  0  0
   -0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -2.1387    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 O   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
    0.0000   -0.0000    0.0000 C   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
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297    1.2798    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4675    1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 16 26  1  6  0  0  0
 16 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 30 29  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(CC[C@@]2(C)[C@H](C)C[C@H](OC(C)=O)[C@]3(COC(C)=O)[C@]2([H])CCC[C@]3(O)CCl)CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H37ClO7/c1-15-12-20(32-17(3)27)24(14-31-16(2)26)19(6-5-9-23(24,29)13-25)22(15,4)10-7-18-8-11-30-21(18)28/h15,18-20,29H,5-14H2,1-4H3/t15-,18?,19-,20+,22+,23+,24+/m1/s1

> <INCHI_KEY>
PIMGCJVHKYCQLI-PMKKWAKVSA-N

> <FORMULA>
C24H37ClO7

> <MOLECULAR_WEIGHT>
473.0

> <EXACT_MASS>
472.2227812

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.15233323305523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-(chloromethyl)-5-hydroxy-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl acetate

> <JCHEM_LOGP>
2.7979218116666673

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.481960212129374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.462790603214612

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
117.57239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-(chloromethyl)-5-hydroxy-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-hexahydro-2H-naphthalen-4a-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0332140 (Ajugarin IX)
Download
PDB for NP0332140 (Ajugarin IX)
HEADER    PROTEIN                                 24-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-NOV-23         0                                  
HETATM    1  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.990  -4.260   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      -2.506  -3.992   0.000  0.00  0.00          Cl+0
HETATM   10  O   UNK     0       0.990  -4.260   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.131   2.627   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.120   3.807   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       4.722   2.389   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       3.748   5.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.054   6.117   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.234   5.127   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.657   3.699   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.473   2.393   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14   30                                             
CONECT    7    6    8   10   11                                             
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   26   27                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   16                                                            
CONECT   27   16   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    6   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

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3D PDB for NP0332140 (Ajugarin IX)
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SMILES for NP0332140 (Ajugarin IX)
[H]C1(CC[C@@]2(C)[C@H](C)C[C@H](OC(C)=O)[C@]3(COC(C)=O)[C@]2([H])CCC[C@]3(O)CCl)CCOC1=O
Download
INCHI for NP0332140 (Ajugarin IX)
InChI=1S/C24H37ClO7/c1-15-12-20(32-17(3)27)24(14-31-16(2)26)19(6-5-9-23(24,29)13-25)22(15,4)10-7-18-8-11-30-21(18)28/h15,18-20,29H,5-14H2,1-4H3/t15-,18?,19-,20+,22+,23+,24+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC24H37ClO7
Average Mass473.0000 Da
Monoisotopic Mass472.22278 Da
IUPAC Name[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-(chloromethyl)-5-hydroxy-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-decahydronaphthalen-4a-yl]methyl acetate
Traditional Name[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-(chloromethyl)-5-hydroxy-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-hexahydro-2H-naphthalen-4a-yl]methyl acetate
CAS Registry NumberNot Available
SMILES
[H]C1(CC[C@@]2(C)[C@H](C)C[C@H](OC(C)=O)[C@]3(COC(C)=O)[C@]2([H])CCC[C@]3(O)CCl)CCOC1=O
InChI Identifier
InChI=1S/C24H37ClO7/c1-15-12-20(32-17(3)27)24(14-31-16(2)26)19(6-5-9-23(24,29)13-25)22(15,4)10-7-18-8-11-30-21(18)28/h15,18-20,29H,5-14H2,1-4H3/t15-,18?,19-,20+,22+,23+,24+/m1/s1
InChI KeyPIMGCJVHKYCQLI-PMKKWAKVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clerodendrum polycephalum
      Not Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentDiterpene lactones  
Alternative Parents
Substituents
  • Clerodane diterpenoid
    • 

  • Diterpenoid
    • 

  • Diterpene lactone
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Alcohol
    • 

  • 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
logP2.8ChemAxon
pKa (Strongest Acidic)13.48ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.57 m³·mol⁻¹ChemAxon
Polarizability50.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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. DOI: 10.1021/acs.jnatprod.3c00743