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Showing NP-Card for Ajugarin VII (NP0332141)

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Record Information
Version2.0
Created at2023-11-24 00:00:40 UTC
Updated at2026-02-26 20:52:33 UTC
NP-MRD IDNP0332141
Natural Product DOIhttps://doi.org/10.57994/1298
Secondary Accession NumbersNone
Natural Product Identification
Common NameAjugarin VII
DescriptionAjugarin VII belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Ajugarin VII was first documented in 2023 (PMID: 37972998). Based on a literature review very few articles have been published on Ajugarin VII.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0332141 (Ajugarin VII)


  Mrv2104 11242300002D          

 33 35  0  0  1  0            999 V2000
    0.1203   -4.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -3.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -3.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -2.0221    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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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  6  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 25  1  6  0  0  0
 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 29 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
Download

3D MOL for NP0332141 (Ajugarin VII)

Download
3D SDF for NP0332141 (Ajugarin VII)

  Mrv2104 11242300002D          

 33 35  0  0  1  0            999 V2000
    0.1203   -4.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -3.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -3.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -2.0221    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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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  6  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 25  1  6  0  0  0
 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 29 28  1  0  0  0  0
  6 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332141

> <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@@H](CCC[C@]23[H])C=O)CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O7/c1-15-12-21(31-17(3)27)24(14-30-16(2)26)19(13-25)6-5-7-20(24)23(15,4)10-8-18-9-11-29-22(18)28/h13,15,18-21H,5-12,14H2,1-4H3/t15-,18?,19+,20-,21+,23+,24+/m1/s1

> <INCHI_KEY>
WKCGAUBIUTWEOU-AYSIPQJISA-N

> <FORMULA>
C24H36O7

> <MOLECULAR_WEIGHT>
436.545

> <EXACT_MASS>
436.246103499

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.31453436927243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.504602582

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.059805768203706

> <JCHEM_PKA_STRONGEST_BASIC>
-6.4242105746082405

> <JCHEM_POLAR_SURFACE_AREA>
95.97000000000003

> <JCHEM_REFRACTIVITY>
112.13849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-formyl-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-octahydronaphthalen-4a-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0332141 (Ajugarin VII)
Download
PDB for NP0332141 (Ajugarin VII)
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       0.225  -7.528   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.255  -6.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761  -6.704   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.779  -4.919   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.810  -3.775   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      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.131   2.627   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.120   3.807   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       4.722   2.389   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       3.748   5.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.054   6.117   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.234   5.127   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.657   3.699   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.473   2.393   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   33  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   13   29                                             
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   25   26                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   15                                                            
CONECT   26   15   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Download
3D PDB for NP0332141 (Ajugarin VII)
Download
SMILES for NP0332141 (Ajugarin VII)
[H]C1(CC[C@@]2(C)[C@H](C)C[C@H](OC(C)=O)[C@@]3(COC(C)=O)[C@@H](CCC[C@]23[H])C=O)CCOC1=O
Download
INCHI for NP0332141 (Ajugarin VII)
InChI=1S/C24H36O7/c1-15-12-21(31-17(3)27)24(14-30-16(2)26)19(13-25)6-5-7-20(24)23(15,4)10-8-18-9-11-29-22(18)28/h13,15,18-21H,5-12,14H2,1-4H3/t15-,18?,19+,20-,21+,23+,24+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC24H36O7
Average Mass436.5450 Da
Monoisotopic Mass436.24610 Da
IUPAC Name[(1S,2R,4S,4aR,5R,8aR)-4-(acetyloxy)-5-formyl-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-formyl-1,2-dimethyl-1-[2-(2-oxooxolan-3-yl)ethyl]-octahydronaphthalen-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@@H](CCC[C@]23[H])C=O)CCOC1=O
InChI Identifier
InChI=1S/C24H36O7/c1-15-12-21(31-17(3)27)24(14-30-16(2)26)19(13-25)6-5-7-20(24)23(15,4)10-8-18-9-11-29-22(18)28/h13,15,18-21H,5-12,14H2,1-4H3/t15-,18?,19+,20-,21+,23+,24+/m1/s1
InChI KeyWKCGAUBIUTWEOU-AYSIPQJISA-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
    • 

  • Fatty alcohol ester
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Fatty acid ester
    • 

  • Fatty acyl
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aldehyde
    • 

  • 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
logP2.5ChemAxon
pKa (Strongest Acidic)17.06ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area95.97 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity112.14 m³·mol⁻¹ChemAxon
Polarizability47.31 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