NP-MRD: Showing NP-Card for Swietemahonin E (NP0066533)

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Record Information

Version

2.0

Created at

2022-04-28 10:47:19 UTC

Updated at

2022-04-28 10:47:19 UTC

NP-MRD ID

NP0066533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Swietemahonin E

Description

Swietemahonin E 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. Swietemahonin E is found in Swietenia mahagoni and Swietenia mahagoni JACQ. . Swietemahonin E was first documented in 2015 (PMID: 26473818). Based on a literature review very few articles have been published on Swietemahonin E (PMID: 30203950).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212472D          

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M  END

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M  END


  Mrv1652304282212472D          

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   -0.1775   -1.2380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -1.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -0.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -0.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2079   -0.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296   -0.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5019    0.5931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1403    1.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6018    2.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248    1.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8862    2.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    1.2194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3249    0.5355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6864   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989   -0.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6136   -1.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8720   -1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2990   -0.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   -0.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995    2.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
  6 18  1  0  0  0  0
  6 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  1  0  0  0
  4 26  1  1  0  0  0
  3 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 36 40  1  0  0  0  0
 29 41  1  1  0  0  0
  2 42  1  1  0  0  0
  1 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@@H]2[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O10/c1-8-15(2)27(36)41-25-20-23(35)31(6,22(29(25,3)4)21(34)28(37)38-7)17-9-11-30(5)18(32(17)26(20)42-32)13-19(33)40-24(30)16-10-12-39-14-16/h8,10,12,14,17-18,20-22,24-26,34H,9,11,13H2,1-7H3/b15-8+/t17-,18-,20-,21-,22+,24+,25-,26-,30-,31-,32-/m1/s1

> <INCHI_KEY>
ZLLFWDPLUDQDKS-IYMMPXKDSA-N

> <FORMULA>
C32H40O10

> <MOLECULAR_WEIGHT>
584.662

> <EXACT_MASS>
584.262147488

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.536848347896296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,9R,10R,13R,14S,15S,17R)-9-(furan-3-yl)-15-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.98970676

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.54931381783111

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.415210260537648

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869674120265398

> <JCHEM_POLAR_SURFACE_AREA>
138.57

> <JCHEM_REFRACTIVITY>
146.55039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,9R,10R,13R,14S,15S,17R)-9-(furan-3-yl)-15-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.028   4.048   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.124   2.805   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.336   1.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.751   1.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.186   0.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.143   2.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.746   3.595   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.368   3.921   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.545   2.605   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.020   2.391   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.762   4.779   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.756   4.519   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.290   3.074   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.741   5.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.207   7.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.192   8.332   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.258   5.443   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.073   1.148   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.315   2.590   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.683  -0.563   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.171  -0.855   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.838   0.308   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.331  -2.311   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.843  -2.604   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.693  -1.726   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.988  -0.326   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.988  -0.036   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.522  -0.163   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.404   1.107   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.729   2.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.590   3.768   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.126   3.660   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.988   4.937   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.801   2.276   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.940   1.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.615  -0.385   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.131  -0.652   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.345  -2.177   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      10.961  -2.852   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.892  -1.744   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.069  -0.282   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.532   4.350   0.000  0.00  0.00           O+0
CONECT    1    2    8   42                                                  
CONECT    2    1    3   30   42                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9   26                                             
CONECT    5    4    6   20                                                  
CONECT    6    5    7   18   19                                             
CONECT    7    6    8   11                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18    6                                                            
CONECT   19    6                                                            
CONECT   20    5   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20                                                            
CONECT   26    4                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35   41                                             
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29   36                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   36                                                       
CONECT   41   29                                                            
CONECT   42    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₀O₁₀

Average Mass

584.6620 Da

Monoisotopic Mass

584.26215 Da

IUPAC Name

(1R,2R,4S,5R,9R,10R,13R,14S,15S,17R)-9-(furan-3-yl)-15-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@@H]2[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C32H40O10/c1-8-15(2)27(36)41-25-20-23(35)31(6,22(29(25,3)4)21(34)28(37)38-7)17-9-11-30(5)18(32(17)26(20)42-32)13-19(33)40-24(30)16-10-12-39-14-16/h8,10,12,14,17-18,20-22,24-26,34H,9,11,13H2,1-7H3/b15-8+/t17-,18-,20-,21-,22+,24+,25-,26-,30-,31-,32-/m1/s1

InChI Key

ZLLFWDPLUDQDKS-IYMMPXKDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Swietenia mahagoni	LOTUS Database	35616633
Swietenia mahagoni JACQ.	Plant	KNApSAcK

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

Mexicanolide
Limonoid skeleton
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Oxepane
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Pyran
Oxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.81	ALOGPS
logP	3.99	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.55 m³·mol⁻¹	ChemAxon
Polarizability	60.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

C00024100

Chemspider ID

10270734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu JS, Zhu LL, Wang GK, Wang G: [Studies on Chemical Constituents from the Fruit of Swietenia macrophylla]. Zhong Yao Cai. 2016 Jul;39(7):1530-5. [PubMed:30203950 ]
Chen LC, Liao HR, Chen PY, Kuo WL, Chang TH, Sung PJ, Wen ZH, Chen JJ: Limonoids from the Seeds of Swietenia macrophylla and Their Anti-Inflammatory Activities. Molecules. 2015 Oct 12;20(10):18551-64. doi: 10.3390/molecules201018551. [PubMed:26473818 ]

Showing NP-Card for Swietemahonin E (NP0066533)

MOL for NP0066533 (Swietemahonin E)

3D MOL for NP0066533 (Swietemahonin E)

3D SDF for NP0066533 (Swietemahonin E)

3D-SDF for NP0066533 (Swietemahonin E)

PDB for NP0066533 (Swietemahonin E)

3D PDB for NP0066533 (Swietemahonin E)

SMILES for NP0066533 (Swietemahonin E)

INCHI for NP0066533 (Swietemahonin E)

Structure for NP0066533 (Swietemahonin E)

3D Structure for NP0066533 (Swietemahonin E)