NP-MRD: Showing NP-Card for ajugamarin a2 chlorohydrin (NP0325365)

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Record Information

Version

2.0

Created at

2022-09-12 06:04:13 UTC

Updated at

2022-09-12 06:04:14 UTC

NP-MRD ID

NP0325365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajugamarin a2 chlorohydrin

Description

Ajugamarin A2 chlorohydrin belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. ajugamarin a2 chlorohydrin is found in Ajuga ciliata. Based on a literature review very few articles have been published on ajugamarin A2 chlorohydrin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208042D          

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M  END

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M  END


  Mrv1652309122208042D          

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    1.2448    4.5315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9626    5.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2107    6.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3054    5.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    4.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    3.6130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1519    3.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    2.9810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5269    2.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    2.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    1.7435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2380    1.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525    1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525    2.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670    1.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    0.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159    0.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5803   -0.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    1.0535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966    3.1243    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  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 11 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  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 43 29  1  1  0  0  0
  8 43  1  0  0  0  0
 15 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325365

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H43ClO11/c1-8-17(2)28(37)43-23-9-10-30(38,15-32)31(16-40-19(4)33)25(42-21(6)35)11-18(3)29(7,27(23)31)13-24(41-20(5)34)22-12-26(36)39-14-22/h8,12,18,23-25,27,38H,9-11,13-16H2,1-7H3/b17-8+/t18-,23-,24+,25+,27-,29+,30+,31-/m1/s1

> <INCHI_KEY>
MQMQEPSKXRDQHX-BEEMTZEWSA-N

> <FORMULA>
C31H43ClO11

> <MOLECULAR_WEIGHT>
627.12

> <EXACT_MASS>
626.2493899

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
64.19623490959984

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,4aR,5S,7R,8S,8aR)-5-(acetyloxy)-8-[(2S)-2-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a-[(acetyloxy)methyl]-4-(chloromethyl)-4-hydroxy-7,8-dimethyl-decahydronaphthalen-1-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
2.999847868999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.472740178606934

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.59413777676996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4668234539329656

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
154.30850000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,4aR,5S,7R,8S,8aR)-5-(acetyloxy)-8-[(2S)-2-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-4a-[(acetyloxy)methyl]-4-(chloromethyl)-4-hydroxy-7,8-dimethyl-hexahydro-1H-naphthalen-1-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.616   1.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.099   1.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.109   2.293   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.636   3.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.407   2.025   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.934   0.578   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.397   3.205   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.870   4.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.646   4.920   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.173   6.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.183   7.547   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.344   8.994   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.517   8.317   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -2.850   7.547   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       1.334   7.279   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.807   8.726   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.710   8.994   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.236  10.441   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.246  11.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.753  10.708   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.324   8.459   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.797   9.906   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.787  11.086   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.260  12.533   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.303  10.818   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.840   8.191   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.367   6.744   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.883   6.477   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.377   5.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.850   4.117   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.711   4.795   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.711   3.255   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.044   2.485   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.378   3.255   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.378   4.795   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.712   2.485   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.377   2.485   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.216   0.953   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.710   0.633   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.083  -0.774   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.940   1.966   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.970   3.111   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.860   5.832   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   43                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   15                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16   21   43                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   43                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   37                                                       
CONECT   43   29    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₃ClO₁₁

Average Mass

627.1200 Da

Monoisotopic Mass

626.24939 Da

IUPAC Name

(1R,4R,4aR,5S,7R,8S,8aR)-5-(acetyloxy)-8-[(2S)-2-(acetyloxy)-2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-4a-[(acetyloxy)methyl]-4-(chloromethyl)-4-hydroxy-7,8-dimethyl-decahydronaphthalen-1-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,4R,4aR,5S,7R,8S,8aR)-5-(acetyloxy)-8-[(2S)-2-(acetyloxy)-2-(5-oxo-2H-furan-3-yl)ethyl]-4a-[(acetyloxy)methyl]-4-(chloromethyl)-4-hydroxy-7,8-dimethyl-hexahydro-1H-naphthalen-1-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H43ClO11/c1-8-17(2)28(37)43-23-9-10-30(38,15-32)31(16-40-19(4)33)25(42-21(6)35)11-18(3)29(7,27(23)31)13-24(41-20(5)34)22-12-26(36)39-14-22/h8,12,18,23-25,27,38H,9-11,13-16H2,1-7H3/b17-8+/t18-,23-,24+,25+,27-,29+,30+,31-/m1/s1

InChI Key

MQMQEPSKXRDQHX-BEEMTZEWSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Pentacarboxylic acid or derivatives
Fatty acid ester
2-furanone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Alkyl chloride
Alkyl halide
Organohalogen compound
Organochloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:69865 )
organochlorine compound (CHEBI:69865 )
butenolide (CHEBI:69865 )
acetate ester (CHEBI:69865 )
diterpene lactone (CHEBI:69865 )
carbobicyclic compound (CHEBI:69865 )

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	ChemAxon
pKa (Strongest Acidic)	5.59	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	154.31 m³·mol⁻¹	ChemAxon
Polarizability	64.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

26633554

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56658113

PDB ID

Not Available

ChEBI ID

69865

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ajugamarin a2 chlorohydrin (NP0325365)

MOL for NP0325365 (ajugamarin a2 chlorohydrin)

3D MOL for NP0325365 (ajugamarin a2 chlorohydrin)

3D SDF for NP0325365 (ajugamarin a2 chlorohydrin)

3D-SDF for NP0325365 (ajugamarin a2 chlorohydrin)

PDB for NP0325365 (ajugamarin a2 chlorohydrin)

3D PDB for NP0325365 (ajugamarin a2 chlorohydrin)

SMILES for NP0325365 (ajugamarin a2 chlorohydrin)

INCHI for NP0325365 (ajugamarin a2 chlorohydrin)

Structure for NP0325365 (ajugamarin a2 chlorohydrin)

3D Structure for NP0325365 (ajugamarin a2 chlorohydrin)