NP-MRD: Showing NP-Card for Ajugamarin H1 (NP0139531)

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Record Information

Version

2.0

Created at

2022-06-29 19:58:37 UTC

Updated at

2022-06-29 19:58:37 UTC

NP-MRD ID

NP0139531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ajugamarin H1

Description

Ajugamarin H1 belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Ajugamarin H1 is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Ajugamarin H1 is found in Ajuga ciliata and Ajuga decumbens. Based on a literature review very few articles have been published on ajugamarin H1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221582D          

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M  END

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M  END


  Mrv1652306292221582D          

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    1.7004   -1.3172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5064   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0619   -0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114   -0.0972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9875    0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5974    0.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0054    0.0789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4499   -0.5311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6439   -0.3550    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3934    0.4310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9489    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7549    0.8649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7520    1.9530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9328    2.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981    3.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6659    3.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088    0.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944   -1.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115   -0.1747    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6141    0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1295    1.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193    1.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160    2.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924    2.0356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1838    1.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -0.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498   -0.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484    0.7236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5897   -0.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3451    0.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0607   -0.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4547    1.3806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6508    2.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3416    2.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433    2.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 13  1  6  0  0  0
 11 14  1  0  0  0  0
 15 14  1  6  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  6  0  0  0
 16 25  1  6  0  0  0
 16 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 27 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 14 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@@H]1CC[C@]2(CO2)[C@]2(COC(C)=O)[C@H](C[C@@H](C)[C@](C)(C[C@H](OC(=O)C(\C)=C\C)C3=CC(=O)OC3)[C@@H]12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h10,14,19,21,25-27,29H,9,11-13,15-18H2,1-8H3/b20-10+/t19-,21+,25+,26-,27-,29+,32-,33-,34+/m0/s1

> <INCHI_KEY>
YUTIPMUBYJJHKA-LZLNCZMXSA-N

> <FORMULA>
C34H48O11

> <MOLECULAR_WEIGHT>
632.747

> <EXACT_MASS>
632.319662366

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
66.87188112463703

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-2-[(1R,4R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-4-{[(2S)-2-methylbutanoyl]oxy}-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
4.495050375666665

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.589669125084417

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204060365071419

> <JCHEM_POLAR_SURFACE_AREA>
144.03

> <JCHEM_REFRACTIVITY>
161.54980000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-2-[(1R,4R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-5,6-dimethyl-4-{[(2S)-2-methylbutanoyl]oxy}-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-5-yl]-1-(5-oxo-2H-furan-3-yl)ethyl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.854  -9.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.033  -8.627   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.052  -7.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.482  -6.725   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.134  -5.780   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.658  -6.243   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.938  -4.133   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.174  -2.459   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.679  -2.787   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.716  -1.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.248  -0.181   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.577   1.323   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.715   0.286   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.743   0.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.706  -0.991   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.202  -0.663   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.734   0.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.771   1.943   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.276   1.614   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.270   3.646   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.608   5.393   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.237   6.287   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.976   6.728   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.763   0.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.923  -2.243   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.441  -1.146   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.888  -0.326   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.146   1.330   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.242   1.998   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.036   3.524   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.150   4.587   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.479   3.800   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.210   2.444   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.572  -0.672   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.133  -0.048   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.877   1.351   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.701  -0.539   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.111   0.281   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.447  -0.486   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.220  -2.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.750   1.641   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.449   2.577   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.815   4.300   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       8.104   5.249   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.681   5.595   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11   13                                                       
CONECT   13   12   11                                                       
CONECT   14   11   15   19   41                                             
CONECT   15   14    8   16                                                  
CONECT   16   15   17   25   26                                             
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17                                                            
CONECT   25   16                                                            
CONECT   26   16   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   28                                                       
CONECT   34   27   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37                                                            
CONECT   41   14   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₈O₁₁

Average Mass

632.7470 Da

Monoisotopic Mass

632.31966 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@@H]1CC[C@]2(CO2)[C@]2(COC(C)=O)[C@H](C[C@@H](C)[C@](C)(C[C@H](OC(=O)C(\C)=C\C)C3=CC(=O)OC3)[C@@H]12)OC(C)=O

InChI Identifier

InChI=1S/C34H48O11/c1-9-19(3)30(38)44-25-11-12-33(17-42-33)34(18-41-22(6)35)27(43-23(7)36)13-21(5)32(8,29(25)34)15-26(24-14-28(37)40-16-24)45-31(39)20(4)10-2/h10,14,19,21,25-27,29H,9,11-13,15-18H2,1-8H3/b20-10+/t19-,21+,25+,26-,27-,29+,32-,33-,34+/m0/s1

InChI Key

YUTIPMUBYJJHKA-LZLNCZMXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajuga ciliata	LOTUS Database	35616633
Ajuga decumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Fatty acid ester
2-furanone
Fatty acyl
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:69875 )
butenolide (CHEBI:69875 )
acetate ester (CHEBI:69875 )
diterpene lactone (CHEBI:69875 )
oxaspiro compound (CHEBI:69875 )

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

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

10258995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21629954

PDB ID

Not Available

ChEBI ID

69875

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ajugamarin H1 (NP0139531)

MOL for NP0139531 (Ajugamarin H1)

3D MOL for NP0139531 (Ajugamarin H1)

3D SDF for NP0139531 (Ajugamarin H1)

3D-SDF for NP0139531 (Ajugamarin H1)

PDB for NP0139531 (Ajugamarin H1)

3D PDB for NP0139531 (Ajugamarin H1)

SMILES for NP0139531 (Ajugamarin H1)

INCHI for NP0139531 (Ajugamarin H1)

Structure for NP0139531 (Ajugamarin H1)

3D Structure for NP0139531 (Ajugamarin H1)