NP-MRD: Showing NP-Card for 6-Acetylswietenolide (NP0066524)

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Record Information

Version

2.0

Created at

2022-04-28 10:46:51 UTC

Updated at

2022-04-28 10:46:51 UTC

NP-MRD ID

NP0066524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Acetylswietenolide

Description

(AlphaR,4R,4aR,6aS,7R,8S,10R, 11S)-Methyl alpha-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[f][2]benzopyran-8-acetate 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. 6-Acetylswietenolide is found in Khaya grandifoliola , Swietenia macrophylla, Swietenia mahagoni and Swietenia mahagoni JACQ. . Based on a literature review very few articles have been published on (alphaR,4R,4aR,6aS,7R,8S,10R, 11S)-Methyl alpha-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[f][2]benzopyran-8-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212462D          

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M  END

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M  END


  Mrv1652304282212462D          

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   -0.9235   -1.0472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5449   -1.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854   -2.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3256   -1.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989    0.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383    1.3712    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  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 11 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
  8 21  1  1  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  1  1  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 26  1  1  0  0  0
  3 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  2 36  1  0  0  0  0
  2 37  1  0  0  0  0
  1 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](OC(C)=O)[C@H]1C(C)(C)[C@H](O)[C@@H]2CC3=C4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)CC[C@@H]3[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-14(30)37-21(26(34)35-6)22-27(2,3)23(32)17-11-16-18(29(22,5)24(17)33)7-9-28(4)19(16)12-20(31)38-25(28)15-8-10-36-13-15/h8,10,13,17-18,21-23,25,32H,7,9,11-12H2,1-6H3/t17-,18-,21+,22-,23+,25-,28+,29+/m0/s1

> <INCHI_KEY>
CFADVMDMXMEBDZ-SEIIJOFPSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.92255029232142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-(acetyloxy)-2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.6852499693333316

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.190055550482203

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.297550513129568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888856385525942

> <JCHEM_POLAR_SURFACE_AREA>
129.34

> <JCHEM_REFRACTIVITY>
133.23000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-(methyl (acetyloxy)[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate)

> <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       1.085   1.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.401   0.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.893  -1.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.273  -2.123   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.732  -1.631   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.416  -0.251   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.953  -0.153   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.806  -1.435   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.122  -2.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.585  -2.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.343  -1.338   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.027   0.042   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.174   1.324   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.857   2.704   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.637   1.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.196  -2.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.735  -2.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.150  -4.166   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.868  -5.019   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.660  -4.063   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.659  -2.717   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.924   1.208   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.544   1.892   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.907  -0.082   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.724   0.905   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.169  -3.660   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.267  -2.453   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.031  -3.964   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.488  -4.461   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.129  -4.977   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.831  -6.488   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.724  -1.955   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.884  -2.968   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.586  -4.479   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.341  -2.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.931   0.792   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.023  -0.567   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.071   2.560   0.000  0.00  0.00           O+0
CONECT    1    2   23   38                                                  
CONECT    2    1    3   36   37                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5   24   26                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   11   21                                             
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16   11   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21    8                                                            
CONECT   22    6   23                                                       
CONECT   23   22    1   24                                                  
CONECT   24   23    4   25                                                  
CONECT   25   24                                                            
CONECT   26    4                                                            
CONECT   27    3   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    2                                                            
CONECT   37    2                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(AlphaR,4R,4ar,6as,7R,8S,10R, 11S)-methyl a-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[F][2]benzopyran-8-acetate	Generator
(AlphaR,4R,4ar,6as,7R,8S,10R, 11S)-methyl a-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[F][2]benzopyran-8-acetic acid	Generator
(AlphaR,4R,4ar,6as,7R,8S,10R, 11S)-methyl alpha-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[F][2]benzopyran-8-acetic acid	Generator
(AlphaR,4R,4ar,6as,7R,8S,10R, 11S)-methyl α-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[F][2]benzopyran-8-acetate	Generator
(AlphaR,4R,4ar,6as,7R,8S,10R, 11S)-methyl α-acetoxy-4-(3-furanyl)-10-hydroxy-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[F][2]benzopyran-8-acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl (2R)-2-(acetyloxy)-2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

Traditional Name

(R)-(methyl (acetyloxy)[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate)

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](OC(C)=O)[C@H]1C(C)(C)[C@H](O)[C@@H]2CC3=C4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)CC[C@@H]3[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C29H36O9/c1-14(30)37-21(26(34)35-6)22-27(2,3)23(32)17-11-16-18(29(22,5)24(17)33)7-9-28(4)19(16)12-20(31)38-25(28)15-8-10-36-13-15/h8,10,13,17-18,21-23,25,32H,7,9,11-12H2,1-6H3/t17-,18-,21+,22-,23+,25-,28+,29+/m0/s1

InChI Key

CFADVMDMXMEBDZ-SEIIJOFPSA-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
Khaya grandifoliola	Plant	KNApSAcK
Swietenia macrophylla	LOTUS Database	35616633
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

Limonoid skeleton
Mexicanolide
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Cyclic alcohol
Furan
Methyl ester
Heteroaromatic compound
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	3.07	ALOGPS
logP	2.69	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.34 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.23 m³·mol⁻¹	ChemAxon
Polarizability	53.92 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

10404659

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6-Acetylswietenolide (NP0066524)

MOL for NP0066524 (6-Acetylswietenolide)

3D MOL for NP0066524 (6-Acetylswietenolide)

3D SDF for NP0066524 (6-Acetylswietenolide)

3D-SDF for NP0066524 (6-Acetylswietenolide)

PDB for NP0066524 (6-Acetylswietenolide)

3D PDB for NP0066524 (6-Acetylswietenolide)

SMILES for NP0066524 (6-Acetylswietenolide)

INCHI for NP0066524 (6-Acetylswietenolide)

Structure for NP0066524 (6-Acetylswietenolide)

3D Structure for NP0066524 (6-Acetylswietenolide)