NP-MRD: Showing NP-Card for andirolide N (NP0041388)

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Record Information

Version

2.0

Created at

2021-06-20 23:18:44 UTC

Updated at

2021-06-30 00:15:52 UTC

NP-MRD ID

NP0041388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

andirolide N

Provided By

JEOL Database JEOL Logo

Description

andirolide N is found in Carapa guianensis, Meliaceae. andirolide N was first documented in 2017 (PMID: 28001380). Based on a literature review very few articles have been published on Andirolide N.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101183D          

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M  END

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M  END


  Mrv1652306212101183D          

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    0.4286   -1.8608    2.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0041388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12O[C@]34C5=C([H])C(=O)O[C@@]([H])(C6=C([H])OC([H])=C6[H])[C@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3([H])[C@](C(=O)[C@@]1([H])C4([H])[H])(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-23(2)17(10-19(28)32-5)25(4)16-6-8-24(3)18(11-20(29)34-22(24)14-7-9-33-13-14)26(16)12-15(21(25)30)27(23,31)35-26/h7,9,11,13,15-17,22,31H,6,8,10,12H2,1-5H3/t15-,16-,17+,22+,24-,25-,26+,27-/m1/s1

> <INCHI_KEY>
URGZBBCARSDFSL-FWYRRKFGSA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.052226176702774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1S,2R,5R,6R,11S,13R,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7,18-dioxapentacyclo[11.3.1.1^{11,14}.0^{2,11}.0^{5,10}]octadec-9-en-16-yl]acetate

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
3.5646465496666657

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.684011039827716

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.302836233371915

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8762218108874404

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000001

> <JCHEM_REFRACTIVITY>
122.3149

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,2R,5R,6R,11S,13R,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7,18-dioxapentacyclo[11.3.1.1^{11,14}.0^{2,11}.0^{5,10}]octadec-9-en-16-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 72  0  0  0  0  0  0  0  0999 V2000
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 14 50  1  0
 20 55  1  1
 22 58  1  0
 22 59  1  0
 21 56  1  0
 21 57  1  0
 26 63  1  0
 19 52  1  0
 19 53  1  0
 19 54  1  0
 30 64  1  6
 35 67  1  0
 33 66  1  0
 32 65  1  0
 24 60  1  0
 24 61  1  0
 24 62  1  0
  6 41  1  6
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  8 43  1  0
  8 44  1  0
  5 39  1  0
  5 40  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  9 45  1  0
  9 46  1  0
  9 47  1  0
 11 48  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.931   4.566  -4.557  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.167   4.708  -3.358  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.371   3.640  -3.077  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.269   2.636  -3.766  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.601   3.899  -1.798  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.141   2.608  -1.068  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.171   2.877  -0.198  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.403   2.788  -1.139  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.215   4.286   0.449  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.260   1.794   0.911  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.456   1.881   1.665  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.250   0.497   0.291  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.924  -0.196   0.743  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.148   0.366   2.158  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.920   1.832   1.892  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.151   2.341   1.186  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.966   3.070   1.743  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.288   1.856  -0.253  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.722   2.138  -0.746  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.112   0.269  -0.173  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.132  -0.386  -1.572  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.112  -1.502  -1.767  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.021  -2.466  -0.569  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.387  -3.146  -0.312  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.618  -1.683   0.683  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.072  -2.333   1.642  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.408  -3.766   1.565  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.780  -4.371   2.561  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.264  -4.360   0.361  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.104  -3.527  -0.809  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.101  -4.404  -2.014  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.816  -5.636  -2.090  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.714  -6.072  -3.390  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.022  -5.200  -4.123  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.402  -4.203  -3.286  0.00  0.00           C+0
HETATM   36  H   UNK     0      -3.269   4.472  -5.423  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.601   3.703  -4.484  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.539   5.466  -4.681  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.738   4.491  -2.121  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.198   4.521  -1.123  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.824   1.917  -1.857  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.504   1.789  -1.577  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.326   3.501  -1.966  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.333   3.014  -0.607  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.694   4.519   1.011  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.060   4.377   1.141  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.346   5.076  -0.298  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.167   1.619   1.057  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.397   0.033   2.881  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.140   0.129   2.557  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.731   2.418   2.796  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.882   1.784  -1.768  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.976   3.202  -0.703  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.460   1.630  -0.112  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.014  -0.112   0.334  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.002   0.337  -2.380  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.138  -0.795  -1.739  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.129  -1.052  -1.960  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.384  -2.041  -2.682  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.788  -3.588  -1.230  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.138  -2.442   0.060  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.315  -3.945   0.435  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.429  -1.861   2.549  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.067  -3.013  -0.953  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.334  -6.144  -1.288  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.082  -6.938  -3.922  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.013  -3.432  -3.735  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3   39   40                                             
CONECT    6   18    7    5   41                                             
CONECT    7   10    6    8    9                                             
CONECT    8    7   42   43   44                                             
CONECT    9    7   45   46   47                                             
CONECT   10   15    7   11   12                                             
CONECT   11   10   48                                                       
CONECT   12   13   10                                                       
CONECT   13   14   20   25   12                                             
CONECT   14   15   13   49   50                                             
CONECT   15   14   10   16   51                                             
CONECT   16   18   17   15                                                  
CONECT   17   16                                                            
CONECT   18   16    6   19   20                                             
CONECT   19   18   52   53   54                                             
CONECT   20   13   21   18   55                                             
CONECT   21   20   22   56   57                                             
CONECT   22   23   21   58   59                                             
CONECT   23   24   22   25   30                                             
CONECT   24   23   60   61   62                                             
CONECT   25   23   26   13                                                  
CONECT   26   25   27   63                                                  
CONECT   27   28   26   29                                                  
CONECT   28   27                                                            
CONECT   29   30   27                                                       
CONECT   30   23   29   31   64                                             
CONECT   31   35   32   30                                                  
CONECT   32   33   31   65                                                  
CONECT   33   34   32   66                                                  
CONECT   34   35   33                                                       
CONECT   35   31   34   67                                                  
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48   11                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   24                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   26                                                            
CONECT   64   30                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   35                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

RDKit          3D

67 72  0  0  0  0  0  0  0  0999 V2000
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  9 45  1  0
  9 46  1  0
  9 47  1  0
 11 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

methyl 2-[(1S,2R,5R,6R,11S,13R,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7,18-dioxapentacyclo[11.3.1.1^{11,14}.0^{2,11}.0^{5,10}]octadec-9-en-16-yl]acetate

Traditional Name

methyl [(1S,2R,5R,6R,11S,13R,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7,18-dioxapentacyclo[11.3.1.1^{11,14}.0^{2,11}.0^{5,10}]octadec-9-en-16-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12O[C@]34C5=C([H])C(=O)O[C@@]([H])(C6=C([H])OC([H])=C6[H])[C@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@]3([H])[C@](C(=O)[C@@]1([H])C4([H])[H])(C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C2(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H32O8/c1-23(2)17(10-19(28)32-5)25(4)16-6-8-24(3)18(11-20(29)34-22(24)14-7-9-33-13-14)26(16)12-15(21(25)30)27(23,31)35-26/h7,9,11,13,15-17,22,31H,6,8,10,12H2,1-5H3/t15-,16-,17+,22+,24-,25-,26+,27-/m1/s1

InChI Key

URGZBBCARSDFSL-FWYRRKFGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Carapa guianensis	JEOL database	Tanaka, Y., et al, Tetrahedron 68, 3669 (2012)

Chemical Taxonomy

Classification

Not classified

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	2.83	ALOGPS
logP	3.56	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.31 m³·mol⁻¹	ChemAxon
Polarizability	50.05 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

57522883

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schuppe AW, Newhouse TR: Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (+/-)-Andirolide N via (+/-)-8alpha-Hydroxycarapin. J Am Chem Soc. 2017 Jan 18;139(2):631-634. doi: 10.1021/jacs.6b12268. Epub 2017 Jan 5. [PubMed:28001380 ]
Tanaka, Y., et al. (2012). Tanaka, Y., et al, Tetrahedron 68, 3669 (2012). Tetrahedron.

Showing NP-Card for andirolide N (NP0041388)

MOL for NP0041388 (andirolide N)

3D MOL for NP0041388 (andirolide N)

3D SDF for NP0041388 (andirolide N)

3D-SDF for NP0041388 (andirolide N)

PDB for NP0041388 (andirolide N)

3D PDB for NP0041388 (andirolide N)

SMILES for NP0041388 (andirolide N)

INCHI for NP0041388 (andirolide N)

Structure for NP0041388 (andirolide N)

3D Structure for NP0041388 (andirolide N)