NP-MRD: Showing NP-Card for ajugamarin a1 (NP0214911)

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Record Information

Version

2.0

Created at

2022-09-05 14:20:26 UTC

Updated at

2022-09-05 14:20:26 UTC

NP-MRD ID

NP0214911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajugamarin a1

Description

Ajugamarin A1 belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Ajugamarin A1 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 a1 is found in Ajuga ciliata, Ajuga decumbens and Ajuga nipponensis. ajugamarin a1 was first documented in 2023 (PMID: 35726426). Based on a literature review very few articles have been published on ajugamarin A1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216202D          

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M  END

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M  END


  Mrv1652309052216202D          

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   -0.9527    2.3912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2745    1.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776    2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0743    2.9966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878    1.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8442    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4801    1.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  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  6  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  1  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  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  1  0  0  0  0
 33 38  1  0  0  0  0
 39 28  1  1  0  0  0
  8 39  1  0  0  0  0
 14 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/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](O)C3=CC(=O)OC3)[C@@H]12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O10/c1-7-16(2)26(34)39-22-8-9-28(14-37-28)29(15-36-18(4)30)23(38-19(5)31)10-17(3)27(6,25(22)29)12-21(32)20-11-24(33)35-13-20/h7,11,17,21-23,25,32H,8-10,12-15H2,1-6H3/b16-7+/t17-,21+,22-,23+,25-,27+,28+,29-/m1/s1

> <INCHI_KEY>
HZPBAEMQRBYDPW-CJARLIFWSA-N

> <FORMULA>
C29H40O10

> <MOLECULAR_WEIGHT>
548.629

> <EXACT_MASS>
548.262147488

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
57.33675948769091

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.365834175

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.042232851860525

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.76697682750473

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0317774432389104

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
138.5959

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.812   9.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.225   8.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.243   7.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.747   6.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.794   6.016   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.299   6.345   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.327   4.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.364   3.410   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.868   3.739   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.905   2.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.438   1.133   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.905   0.666   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.766  -0.371   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.933   0.805   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.103  -0.726   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.513  -1.344   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.683  -2.875   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.442  -3.787   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.093  -3.494   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.465  -0.663   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.502  -1.801   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.035  -3.269   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.204  -4.799   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.530  -3.597   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.039  -0.991   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.076   0.147   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.581  -0.181   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.608   1.614   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.671   3.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.135   1.820   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.720   3.245   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.778   4.464   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.246   3.450   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.976   4.806   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.491   4.530   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.605   5.594   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.697   3.004   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.309   2.337   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.896   1.943   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   39                                                  
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   20   39                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   39                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   33                                                       
CONECT   39   28    8   14                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₁₀

Average Mass

548.6290 Da

Monoisotopic Mass

548.26215 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(/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](O)C3=CC(=O)OC3)[C@@H]12)OC(C)=O

InChI Identifier

InChI=1S/C29H40O10/c1-7-16(2)26(34)39-22-8-9-28(14-37-28)29(15-36-18(4)30)23(38-19(5)31)10-17(3)27(6,25(22)29)12-21(32)20-11-24(33)35-13-20/h7,11,17,21-23,25,32H,8-10,12-15H2,1-6H3/b16-7+/t17-,21+,22-,23+,25-,27+,28+,29-/m1/s1

InChI Key

HZPBAEMQRBYDPW-CJARLIFWSA-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
Ajuga nipponensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:69878 )
butenolide (CHEBI:69878 )
acetate ester (CHEBI:69878 )
diterpene lactone (CHEBI:69878 )
oxaspiro compound (CHEBI:69878 )

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	2.37	ChemAxon
pKa (Strongest Acidic)	5.77	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

4944870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440613

PDB ID

Not Available

ChEBI ID

69878

Good Scents ID

Not Available

References

General References

Zacchaeus Olatunde O, Yong J, Lu C: New neo-Clerodane Diterpenoids Isolated from Ajuga decumbens Thunb., Planted at Pingtan Island of Fujian Province with the Potent Anticancer Activity. Anticancer Agents Med Chem. 2023;23(2):237-244. doi: 10.2174/1871520622666220620151225. [PubMed:35726426 ]
LOTUS database [Link]

Showing NP-Card for ajugamarin a1 (NP0214911)

MOL for NP0214911 (ajugamarin a1)

3D MOL for NP0214911 (ajugamarin a1)

3D SDF for NP0214911 (ajugamarin a1)

3D-SDF for NP0214911 (ajugamarin a1)

PDB for NP0214911 (ajugamarin a1)

3D PDB for NP0214911 (ajugamarin a1)

SMILES for NP0214911 (ajugamarin a1)

INCHI for NP0214911 (ajugamarin a1)

Structure for NP0214911 (ajugamarin a1)

3D Structure for NP0214911 (ajugamarin a1)