NP-MRD: Showing NP-Card for frajunolide k (NP0179048)

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Record Information

Version

2.0

Created at

2022-09-03 17:09:54 UTC

Updated at

2022-09-03 17:09:54 UTC

NP-MRD ID

NP0179048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

frajunolide k

Description

FRAJUNOLIDE K belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. frajunolide k is found in Junceella fragilis. Based on a literature review very few articles have been published on FRAJUNOLIDE K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219092D          

 43 45  0  0  1  0            999 V2000
   -1.4214    5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930    4.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5429    3.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.5724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    3.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    2.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032219092D          

 43 45  0  0  1  0            999 V2000
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   -1.1782    0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987    0.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4836    1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3041    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480    1.9341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8625    2.3466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4756    1.7946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    2.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8733    1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4318    2.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1981    3.1003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6106    2.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0186    3.0140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8255    3.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541    3.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1611    3.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410    4.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0265    3.9073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4135    4.4593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7490    5.2130    0.0000 Cl  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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  6  0  0  0
 17 28  1  0  0  0  0
 28 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
 29 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 41 40  1  1  0  0  0
 34 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0179048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OCC(=O)O[C@H]1\C=C/C(=C)[C@H](Cl)[C@@H]2OC(=O)[C@H](C)[C@@]2(O)[C@@H](OC(C)=O)[C@H]2C(=C)CC[C@H](OC(C)=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H41ClO11/c1-15(2)13-23(35)39-14-24(36)42-22-12-10-17(4)26(32)28-31(38,18(5)29(37)43-28)27(41-20(7)34)25-16(3)9-11-21(30(22,25)8)40-19(6)33/h10,12,15,18,21-22,25-28,38H,3-4,9,11,13-14H2,1-2,5-8H3/b12-10-/t18-,21-,22-,25+,26-,27-,28-,30+,31+/m0/s1

> <INCHI_KEY>
GHIWIJGIRLTZJA-LSVMNBOYSA-N

> <FORMULA>
C31H41ClO11

> <MOLECULAR_WEIGHT>
625.11

> <EXACT_MASS>
624.2337398

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.87079068777175

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-12-yl]oxy}-2-oxoethyl 3-methylbutanoate

> <JCHEM_LOGP>
3.1589166929999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.36218528818829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.95258015494644

> <JCHEM_POLAR_SURFACE_AREA>
151.73000000000002

> <JCHEM_REFRACTIVITY>
152.04250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-12-yl]oxy}-2-oxoethyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.653   9.991   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.974   8.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.640   7.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.013   6.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   4.802   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.000   4.032   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   4.802   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   6.342   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   4.032   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   4.802   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335   4.032   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   2.492   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668   4.802   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   4.802   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   2.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.478   3.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.947   3.610   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.573   2.525   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.041   2.686   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.864   1.441   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.395   1.601   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.237   0.034   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.199   1.119   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.731   0.958   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.636   2.203   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.168   2.043   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.010   3.610   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.343   4.380   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.488   3.350   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.952   3.826   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.097   2.795   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.273   5.332   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.970   5.787   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.740   4.454   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.501   5.626   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.008   5.946   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.128   7.033   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -9.634   7.353   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.983   8.064   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.650   7.294   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.505   8.324   0.000  0.00  0.00           C+0
HETATM   43 Cl   UNK     0      -5.131   9.731   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   19   28                                             
CONECT   18   17                                                            
CONECT   19   17   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   17   29                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   36   41                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   34   42                                                  
CONECT   42   41    2   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₁ClO₁₁

Average Mass

625.1100 Da

Monoisotopic Mass

624.23374 Da

IUPAC Name

2-{[(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S)-2,14-bis(acetyloxy)-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-12-yl]oxy}-2-oxoethyl 3-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OCC(=O)O[C@H]1\C=C/C(=C)[C@H](Cl)[C@@H]2OC(=O)[C@H](C)[C@@]2(O)[C@@H](OC(C)=O)[C@H]2C(=C)CC[C@H](OC(C)=O)[C@]12C

InChI Identifier

InChI=1S/C31H41ClO11/c1-15(2)13-23(35)39-14-24(36)42-22-12-10-17(4)26(32)28-31(38,18(5)29(37)43-28)27(41-20(7)34)25-16(3)9-11-21(30(22,25)8)40-19(6)33/h10,12,15,18,21-22,25-28,38H,3-4,9,11,13-14H2,1-2,5-8H3/b12-10-/t18-,21-,22-,25+,26-,27-,28-,30+,31+/m0/s1

InChI Key

GHIWIJGIRLTZJA-LSVMNBOYSA-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
Junceella fragilis	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
Briarane diterpenoid
Pentacarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Alkyl halide
Alkyl chloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.16	ChemAxon
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	151.73 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	152.04 m³·mol⁻¹	ChemAxon
Polarizability	62.87 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

C00039227

Chemspider ID

24714641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25111817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for frajunolide k (NP0179048)

MOL for NP0179048 (frajunolide k)

3D MOL for NP0179048 (frajunolide k)

3D SDF for NP0179048 (frajunolide k)

3D-SDF for NP0179048 (frajunolide k)

PDB for NP0179048 (frajunolide k)

3D PDB for NP0179048 (frajunolide k)

SMILES for NP0179048 (frajunolide k)

INCHI for NP0179048 (frajunolide k)

Structure for NP0179048 (frajunolide k)

3D Structure for NP0179048 (frajunolide k)