NP-MRD: Showing NP-Card for aphanalide J (NP0043483)

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Record Information

Version

2.0

Created at

2021-06-21 00:52:55 UTC

Updated at

2021-06-30 00:19:11 UTC

NP-MRD ID

NP0043483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aphanalide J

Provided By

JEOL Database JEOL Logo

Description

CHEMBL2392327 belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. aphanalide J is found in Aphanamixis grandifolia. It was first documented in 2013 (Zhang, Y., et al.). Based on a literature review very few articles have been published on CHEMBL2392327.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102523D          

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M  END


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    3.3452   -1.2189    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0043483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]([H])(C2=C([H])OC([H])=C2[H])[C@]2(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])[C@@]4(C([H])([H])[H])[C@]([H])(O[C@@]124)C([H])([H])[C@]1([H])[C@@]3(C([H])=C([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O7/c1-22(2)15-11-17-25(5)20(23(15,3)8-6-18(28)33-22)19(29)21(30)24(4)14(13-7-9-31-12-13)10-16(27)26(24,25)32-17/h6-9,12,14-17,19-21,27,29-30H,10-11H2,1-5H3/t14-,15-,16+,17+,19+,20+,21-,23-,24+,25+,26-/m0/s1

> <INCHI_KEY>
PKPHRMXBBLNQQE-VSFHLZNESA-N

> <FORMULA>
C26H34O7

> <MOLECULAR_WEIGHT>
458.551

> <EXACT_MASS>
458.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.6989611035349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,8R,10R,12S,13R,15R,16R,17R,18R,19S)-15-(furan-3-yl)-13,17,18-trihydroxy-2,7,7,16,19-pentamethyl-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadec-3-en-5-one

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
1.6847766753333346

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.01314509240855

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.325864986198734

> <JCHEM_PKA_STRONGEST_BASIC>
-2.788789929349052

> <JCHEM_POLAR_SURFACE_AREA>
109.36000000000001

> <JCHEM_REFRACTIVITY>
118.59670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,8R,10R,12S,13R,15R,16R,17R,18R,19S)-15-(furan-3-yl)-13,17,18-trihydroxy-2,7,7,16,19-pentamethyl-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadec-3-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 72  0  0  0  0  0  0  0  0999 V2000
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 33 66  1  0
 33 67  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      -5.326  -0.181   2.939  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.615   0.952   2.164  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.345   2.076   3.180  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.554   1.525   1.234  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.908   0.744   0.193  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.827  -0.055   0.175  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.142   1.143  -0.991  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.826   1.398  -0.975  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.795   1.238   0.155  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.378   2.666   0.524  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.331   0.409   1.424  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.215   0.050   2.442  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.911  -0.470   1.853  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.965  -1.788   1.187  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.153  -1.311   0.297  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.494  -1.819   0.880  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.522  -0.854   0.675  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.802  -3.053   0.049  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.454  -2.588  -1.369  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.517  -3.679  -2.398  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.254  -5.073  -2.249  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.456  -5.649  -3.481  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.832  -4.711  -4.384  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.872  -3.526  -3.726  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.079  -1.835  -1.195  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.101  -2.804  -1.422  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.055  -0.572  -2.118  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.086  -0.899  -3.510  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.123   0.420  -1.869  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.731   1.743  -2.218  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.630   0.351  -0.423  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.432   0.150   0.539  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.563   1.291   0.676  0.00  0.00           C+0
HETATM   34  H   UNK     0      -4.744  -0.518   3.802  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.307   0.153   3.299  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.511  -1.051   2.300  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.733   1.743   4.023  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.865   2.943   2.721  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.290   2.451   3.592  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.727   1.245  -1.897  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.420   1.785  -1.912  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.850   2.711   1.479  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.738   3.114  -0.244  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.248   3.326   0.619  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.647  -0.559   1.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.961   0.945   3.019  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.586  -0.686   3.163  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.159  -0.499   2.656  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.442  -2.047   1.949  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.345  -1.219   1.047  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.851  -3.359   0.123  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.170  -3.891   0.366  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.223  -1.854  -1.656  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.948  -5.599  -1.355  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.380  -6.659  -3.859  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.161  -2.671  -4.324  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.082  -2.352  -1.276  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.111  -3.202  -2.441  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.049  -3.655  -0.733  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.986  -0.013  -1.956  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.649  -1.506  -3.704  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.939   0.158  -2.554  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.305   1.680  -3.094  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.156  -0.607  -0.463  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.096   2.240   0.930  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.133   1.447  -0.243  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.282   1.100   1.479  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2   11    4    1    3                                             
CONECT    3    2   37   38   39                                             
CONECT    4    5    2                                                       
CONECT    5    6    4    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   40                                                  
CONECT    8    9    7   41                                                  
CONECT    9    8   10   11   31                                             
CONECT   10    9   42   43   44                                             
CONECT   11   12    2   45    9                                             
CONECT   12   11   13   46   47                                             
CONECT   13   12   32   14   48                                             
CONECT   14   15   13                                                       
CONECT   15   16   14   32   25                                             
CONECT   16   15   18   17   49                                             
CONECT   17   16   50                                                       
CONECT   18   16   19   51   52                                             
CONECT   19   18   25   20   53                                             
CONECT   20   19   24   21                                                  
CONECT   21   22   20   54                                                  
CONECT   22   23   21   55                                                  
CONECT   23   24   22                                                       
CONECT   24   20   23   56                                                  
CONECT   25   19   26   27   15                                             
CONECT   26   25   57   58   59                                             
CONECT   27   28   25   29   60                                             
CONECT   28   27   61                                                       
CONECT   29   30   31   27   62                                             
CONECT   30   29   63                                                       
CONECT   31   32   29   64    9                                             
CONECT   32   13   31   15   33                                             
CONECT   33   32   65   66   67                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   33                                                            
CONECT   67   33                                                            
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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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₇

Average Mass

458.5510 Da

Monoisotopic Mass

458.23045 Da

IUPAC Name

(2R,8R,10R,12S,13R,15R,16R,17R,18R,19S)-15-(furan-3-yl)-13,17,18-trihydroxy-2,7,7,16,19-pentamethyl-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadec-3-en-5-one

Traditional Name

(2R,8R,10R,12S,13R,15R,16R,17R,18R,19S)-15-(furan-3-yl)-13,17,18-trihydroxy-2,7,7,16,19-pentamethyl-6,11-dioxapentacyclo[8.8.1.0^{2,8}.0^{12,16}.0^{12,19}]nonadec-3-en-5-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]([H])(C2=C([H])OC([H])=C2[H])[C@]2(C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])[C@@]4(C([H])([H])[H])[C@]([H])(O[C@@]124)C([H])([H])[C@]1([H])[C@@]3(C([H])=C([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H34O7/c1-22(2)15-11-17-25(5)20(23(15,3)8-6-18(28)33-22)19(29)21(30)24(4)14(13-7-9-31-12-13)10-16(27)26(24,25)32-17/h6-9,12,14-17,19-21,27,29-30H,10-11H2,1-5H3/t14-,15-,16+,17+,19+,20+,21-,23-,24+,25+,26-/m0/s1

InChI Key

PKPHRMXBBLNQQE-VSFHLZNESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, 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
Aphanamixis grandifolia	JEOL database	Zhang, Y., et al, J. Nat. Prod. 76, 1191 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Oxetane
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.67	ALOGPS
logP	1.68	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.6 m³·mol⁻¹	ChemAxon
Polarizability	48.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

30825277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71726252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, Y., et al. (2013). Zhang, Y., et al, J. Nat. Prod. 76, 1191 (2013). J. Nat. Prod..

Showing NP-Card for aphanalide J (NP0043483)

MOL for NP0043483 (aphanalide J)

3D MOL for NP0043483 (aphanalide J)

3D SDF for NP0043483 (aphanalide J)

3D-SDF for NP0043483 (aphanalide J)

PDB for NP0043483 (aphanalide J)

3D PDB for NP0043483 (aphanalide J)

SMILES for NP0043483 (aphanalide J)

INCHI for NP0043483 (aphanalide J)

Structure for NP0043483 (aphanalide J)

3D Structure for NP0043483 (aphanalide J)