NP-MRD: Showing NP-Card for (-)-Swietmanin E (NP0081716)

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Record Information

Version

2.0

Created at

2022-04-29 02:47:54 UTC

Updated at

2022-04-29 02:47:54 UTC

NP-MRD ID

NP0081716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Swietmanin E

Description

(1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-11-en-14-yl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (-)-Swietmanin E is found in Swietenia mahagoni. Based on a literature review very few articles have been published on (1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-11-en-14-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204472D          

 42 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204472D          

 42 46  0  0  1  0            999 V2000
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    2.7495    1.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213    4.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0970    4.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1254    5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615    5.6613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2084    5.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447    4.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    4.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906    4.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8312    5.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505    5.3624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4525    5.6385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2931    6.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3467    2.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3958    3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    1.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7334    0.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0856    0.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8189   -0.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617   -1.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950    0.3587    0.0000 C   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  6  0  0  0
  6  7  2  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
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  6  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 16 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
 13 27  1  1  0  0  0
  4 28  1  1  0  0  0
  3 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 34  1  0  0  0  0
  2 35  1  0  0  0  0
  1 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 39 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)C=C3[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H](O)[C@@H]34)C3=COC=C3)[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O10/c1-8-16(2)25(35)42-28-29(3,4)20(13-21(33)39-7)31(6)19-9-11-30(5)22(18(19)14-32(28,38)27(31)37)23(34)26(36)41-24(30)17-10-12-40-15-17/h8,10,12,14-15,19-20,22-24,28,34,38H,9,11,13H2,1-7H3/b16-8+/t19-,20-,22+,23+,24-,28-,30+,31+,32-/m0/s1

> <INCHI_KEY>
GZUGASVGTFVJJB-MXJLCYGJSA-N

> <FORMULA>
C32H40O10

> <MOLECULAR_WEIGHT>
584.662

> <EXACT_MASS>
584.262147488

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.208201636438105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
3.9092019553333346

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.46117866804159

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.605578354535801

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888737491057467

> <JCHEM_POLAR_SURFACE_AREA>
149.57

> <JCHEM_REFRACTIVITY>
149.42090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.831   4.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.515   5.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.023   6.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.643   7.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.184   7.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.500   5.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.992   4.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.372   3.657   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.268   2.120   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.009   5.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.191   4.643   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.963   5.702   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.110   6.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.794   8.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.331   8.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.573   6.886   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.889   5.506   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.742   4.224   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.059   2.844   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.279   4.322   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.132   3.040   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.720   8.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.181   8.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.234   9.715   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.048  10.568   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.256   9.612   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.257   8.266   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.747   9.208   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.183   8.001   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.885   9.512   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.428  10.010   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.045  10.525   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.747  12.036   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.847   4.756   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.939   6.115   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.844   2.989   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.347   1.532   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.836   1.234   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.360   0.372   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.862  -1.085   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.875  -2.245   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.871   0.670   0.000  0.00  0.00           C+0
CONECT    1    2    8   36                                                  
CONECT    2    1    3   34   35                                             
CONECT    3    2    4   29                                                  
CONECT    4    3    5   10   28                                             
CONECT    5    4    6   15                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9   10                                             
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13   20                                                  
CONECT   13   12   14   16   27                                             
CONECT   14   13   15                                                       
CONECT   15   14    5                                                       
CONECT   16   13   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21                                                  
CONECT   21   20                                                            
CONECT   22   16   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   13                                                            
CONECT   28    4                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    1   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(Furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-11-en-14-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₀

Average Mass

584.6620 Da

Monoisotopic Mass

584.26215 Da

IUPAC Name

(1R,2S,5R,6R,9R,10S,13R,14S,16S)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-11-en-14-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)C=C3[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H](O)[C@@H]34)C3=COC=C3)[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C32H40O10/c1-8-16(2)25(35)42-28-29(3,4)20(13-21(33)39-7)31(6)19-9-11-30(5)22(18(19)14-32(28,38)27(31)37)23(34)26(36)41-24(30)17-10-12-40-15-17/h8,10,12,14-15,19-20,22-24,28,34,38H,9,11,13H2,1-7H3/b16-8+/t19-,20-,22+,23+,24-,28-,30+,31+,32-/m0/s1

InChI Key

GZUGASVGTFVJJB-MXJLCYGJSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
12-alpha-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Cyclohexenone
Delta_valerolactone
Fatty acid ester
Delta valerolactone
Fatty acyl
Pyran
Oxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
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	3.59	ALOGPS
logP	3.91	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	149.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.42 m³·mol⁻¹	ChemAxon
Polarizability	60.21 Å³	ChemAxon
Number of Rings	5	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

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

163104215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Swietmanin E (NP0081716)

MOL for NP0081716 ((-)-Swietmanin E)

3D MOL for NP0081716 ((-)-Swietmanin E)

3D SDF for NP0081716 ((-)-Swietmanin E)

3D-SDF for NP0081716 ((-)-Swietmanin E)

PDB for NP0081716 ((-)-Swietmanin E)

3D PDB for NP0081716 ((-)-Swietmanin E)

SMILES for NP0081716 ((-)-Swietmanin E)

INCHI for NP0081716 ((-)-Swietmanin E)

Structure for NP0081716 ((-)-Swietmanin E)

3D Structure for NP0081716 ((-)-Swietmanin E)