NP-MRD: Showing NP-Card for ajucampylanoid D (NP0333090)

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Record Information

Version

2.0

Created at

2024-05-08 22:16:24 UTC

Updated at

2024-09-03 04:21:10 UTC

NP-MRD ID

NP0333090

Natural Product DOI

https://doi.org/10.57994/2389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajucampylanoid D

Description

Ajucampylanoid D belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. ajucampylanoid D was first documented in 2023 (PMID: 37566645). Based on a literature review very few articles have been published on ajucampylanoid D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01212300522D          

 33 35  0  0  1  0            999 V2000
   -3.9303    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    1.6765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1145    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5434    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2971    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8491    2.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4366    3.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6297    2.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    2.4517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6481    3.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054    2.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.9630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9626    2.1063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    1.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2448    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    0.5558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    1.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216   -0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697    1.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6822    0.9012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  2  0  0  0  0
 20 27  2  0  0  0  0
 17 28  1  6  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 15 32  1  0  0  0  0
 32  2  1  0  0  0  0
 32 33  1  1  0  0  0
M  END


  Mrv2104 01212300522D          

 33 35  0  0  1  0            999 V2000
   -3.9303    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    1.6765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1145    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5434    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2971    1.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8491    2.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4366    3.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6297    2.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178    2.4517    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6481    3.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054    2.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.9630    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9626    2.1063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    1.1877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2448    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5269    0.5558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    0.5558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4744    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1888    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966    1.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216   -0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8697    1.0445    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6822    0.9012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 15 13  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  2  0  0  0  0
 20 27  2  0  0  0  0
 17 28  1  6  0  0  0
 17 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  0  0  0  0
 15 32  1  0  0  0  0
 32  2  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC[C@](O)(COC(=O)CC(=O)OCC)[C@]1(C)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O7/c1-5-31-21(27)14-22(28)32-16-25(29)10-6-7-19-23(3,11-8-18-9-12-30-15-18)17(2)13-20(26)24(19,25)4/h9,12,15,17,19-20,26,29H,5-8,10-11,13-14,16H2,1-4H3/t17-,19-,20+,23+,24+,25+/m1/s1

> <INCHI_KEY>
UYFNKWUUVULSKR-OVRXVIJRSA-N

> <FORMULA>
C25H38O7

> <MOLECULAR_WEIGHT>
450.572

> <EXACT_MASS>
450.261753564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.9329148484065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1R,4aR,5S,6R,8S,8aS)-5-[2-(furan-3-yl)ethyl]-1,8-dihydroxy-5,6,8a-trimethyl-decahydronaphthalen-1-yl]methyl 3-ethyl propanedioate

> <JCHEM_LOGP>
3.6122813003333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.540460217259959

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.631180562230798

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7841107474200797

> <JCHEM_POLAR_SURFACE_AREA>
106.2

> <JCHEM_REFRACTIVITY>
118.18699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1R,4aR,5S,6R,8S,8aS)-5-[2-(furan-3-yl)ethyl]-1,8-dihydroxy-5,6,8a-trimethyl-hexahydro-2H-naphthalen-1-yl]methyl 3-ethyl propanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-23         0                                  
HETATM    1  C   UNK     0      -7.337   1.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.347   3.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.680   3.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.014   3.129   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.348   3.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.755   3.273   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -12.785   4.417   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -12.015   5.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.509   5.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.820   4.577   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.810   5.756   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.303   4.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.313   3.664   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.797   3.932   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.840   2.217   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.324   2.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.850   1.037   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.183   1.037   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.151   0.267   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.484   1.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.818   0.267   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.152   1.037   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.485   0.267   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.819   1.037   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.818  -1.273   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.151  -1.273   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.860   2.217   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.377  -0.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.894  -0.677   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.883   0.503   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.357   1.950   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      -6.873   1.682   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   10   32                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   32                                             
CONECT   16   15                                                            
CONECT   17   15   18   28   29                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22                                                            
CONECT   27   20                                                            
CONECT   28   17                                                            
CONECT   29   17   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   15    2   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₇

Average Mass

450.5720 Da

Monoisotopic Mass

450.26175 Da

IUPAC Name

1-[(1R,4aR,5S,6R,8S,8aS)-5-[2-(furan-3-yl)ethyl]-1,8-dihydroxy-5,6,8a-trimethyl-decahydronaphthalen-1-yl]methyl 3-ethyl propanedioate

Traditional Name

1-[(1R,4aR,5S,6R,8S,8aS)-5-[2-(furan-3-yl)ethyl]-1,8-dihydroxy-5,6,8a-trimethyl-hexahydro-2H-naphthalen-1-yl]methyl 3-ethyl propanedioate

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC[C@](O)(COC(=O)CC(=O)OCC)[C@]1(C)[C@@H](O)C[C@@H](C)[C@]2(C)CCC1=COC=C1

InChI Identifier

InChI=1S/C25H38O7/c1-5-31-21(27)14-22(28)32-16-25(29)10-6-7-19-23(3,11-8-18-9-12-30-15-18)17(2)13-20(26)24(19,25)4/h9,12,15,17,19-20,26,29H,5-8,10-11,13-14,16H2,1-4H3/t17-,19-,20+,23+,24+,25+/m1/s1

InChI Key

UYFNKWUUVULSKR-OVRXVIJRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2024-05-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajuga campylantha		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Fatty alcohol ester
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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
logP	3.61	ChemAxon
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.19 m³·mol⁻¹	ChemAxon
Polarizability	49.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Peng X, Tan Q, Zhang Z, Wu D, Xu J, Zhou H, Gu Q: Discovery of neo-Clerodane Diterpenoids from Ajuga campylantha as Neuroprotective Agents against Ferroptosis and Neuroinflammation. J Nat Prod. 2023 Aug 25;86(8):2006-2021. doi: 10.1021/acs.jnatprod.3c00447. Epub 2023 Aug 11. [PubMed:37566645 ]
DOI: 10.1021/acs.jnatprod.3c00447

Showing NP-Card for ajucampylanoid D (NP0333090)

MOL for NP0333090 (ajucampylanoid D)

3D MOL for NP0333090 (ajucampylanoid D)

3D SDF for NP0333090 (ajucampylanoid D)

3D-SDF for NP0333090 (ajucampylanoid D)

PDB for NP0333090 (ajucampylanoid D)

3D PDB for NP0333090 (ajucampylanoid D)

SMILES for NP0333090 (ajucampylanoid D)

INCHI for NP0333090 (ajucampylanoid D)

Structure for NP0333090 (ajucampylanoid D)

3D Structure for NP0333090 (ajucampylanoid D)