NP-MRD: Showing NP-Card for (-)-3-Acetyl-khayalactone (NP0081759)

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Record Information

Version

2.0

Created at

2022-04-29 02:50:15 UTC

Updated at

2022-04-29 02:50:15 UTC

NP-MRD ID

NP0081759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3-Acetyl-khayalactone

Description

Methyl 2-[(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1¹¹,¹⁴.0¹,¹⁰.0²,⁷]Nonadecan-19-yl]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. (-)-3-Acetyl-khayalactone is found in Khaya ivorensis . Based on a literature review very few articles have been published on methyl 2-[(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1¹¹,¹⁴.0¹,¹⁰.0²,⁷]Nonadecan-19-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204502D          

 39 44  0  0  1  0            999 V2000
    6.2337    0.9872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1 39  1  6  0  0  0
M  END

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M  END


  Mrv1652304292204502D          

 39 44  0  0  1  0            999 V2000
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    4.4748   -2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9092   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701   -1.8325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3471   -2.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1711   -2.6067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9001   -3.2597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -0.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4396    1.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6575    1.6950    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
  1 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 28  1  1  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 13 32  1  0  0  0  0
 29 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 18 37  1  6  0  0  0
 17 38  1  6  0  0  0
  1 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)C[C@]3(O)O[C@]4(CC(=O)[C@H]2OC(C)=O)[C@H](CC[C@]2(C)[C@H]4CC(=O)O[C@H]2C2=COC=C2)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O10/c1-15(30)37-24-17(31)12-28-18(27(4)19(10-21(32)35-5)26(24,3)14-29(27,34)39-28)6-8-25(2)20(28)11-22(33)38-23(25)16-7-9-36-13-16/h7,9,13,18-20,23-24,34H,6,8,10-12,14H2,1-5H3/t18-,19+,20-,23+,24-,25-,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
BAUVGOFRJVLOQU-LBPKBNGPSA-N

> <FORMULA>
C29H36O10

> <MOLECULAR_WEIGHT>
544.597

> <EXACT_MASS>
544.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.09611250324952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1^{11,14}.0^{1,10}.0^{2,7}]nonadecan-19-yl]acetate

> <ALOGPS_LOGP>
2.47

> <JCHEM_LOGP>
2.186107327666667

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.146842430741565

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.623423949982456

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8752283504885714

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
132.13999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1^{11,14}.0^{1,10}.0^{2,7}]nonadecan-19-yl]acetate

> <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      11.636   1.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.786   0.559   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.473  -0.820   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.011  -0.914   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.698  -2.292   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.861   0.371   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      13.173   1.749   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.023   3.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.562   3.100   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.973   4.584   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.689   5.434   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.484   4.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.190   0.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.400   1.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.244   3.052   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.812   3.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.769   1.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.154   0.255   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.680  -0.136   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.404   0.169   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.450  -0.799   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.329   0.997   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.996   1.769   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.998   3.309   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.665   4.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.333   4.077   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335   5.617   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.289  -1.811   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.378  -2.126   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.952  -2.420   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.353  -3.907   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.164  -1.377   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.544  -3.421   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.248  -4.790   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.786  -4.866   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.414  -6.085   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.998  -1.277   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.421   3.200   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.427   3.164   0.000  0.00  0.00           C+0
CONECT    1    2    7   16   39                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    2   14   19   32                                             
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    1                                                       
CONECT   17   14   18   22   38                                             
CONECT   18   17   19   20   37                                             
CONECT   19   18   13                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   28   29                                             
CONECT   22   21   17   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   21                                                            
CONECT   29   21   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   13                                                       
CONECT   33   29   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   18                                                            
CONECT   38   17                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1,.0,.0,]nonadecan-19-yl]acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₁₀

Average Mass

544.5970 Da

Monoisotopic Mass

544.23085 Da

IUPAC Name

methyl 2-[(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1^{11,14}.0^{1,10}.0^{2,7}]nonadecan-19-yl]acetate

Traditional Name

methyl [(1S,2R,6R,7R,10R,11S,12S,14R,15S,19S)-15-(acetyloxy)-6-(furan-3-yl)-12-hydroxy-7,11,14-trimethyl-4,16-dioxo-5,18-dioxapentacyclo[10.5.1.1^{11,14}.0^{1,10}.0^{2,7}]nonadecan-19-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)C[C@]3(O)O[C@]4(CC(=O)[C@H]2OC(C)=O)[C@H](CC[C@]2(C)[C@H]4CC(=O)O[C@H]2C2=COC=C2)[C@]13C

InChI Identifier

InChI=1S/C29H36O10/c1-15(30)37-24-17(31)12-28-18(27(4)19(10-21(32)35-5)26(24,3)14-29(27,34)39-28)6-8-25(2)20(28)11-22(33)38-23(25)16-7-9-36-13-16/h7,9,13,18-20,23-24,34H,6,8,10-12,14H2,1-5H3/t18-,19+,20-,23+,24-,25-,26-,27-,28-,29+/m1/s1

InChI Key

BAUVGOFRJVLOQU-LBPKBNGPSA-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 ivorensis	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
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Alpha-acyloxy ketone
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Methyl ester
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	2.47	ALOGPS
logP	2.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.62	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	6	ChemAxon
Refractivity	132.14 m³·mol⁻¹	ChemAxon
Polarizability	55.1 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

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

163044767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-3-Acetyl-khayalactone (NP0081759)

MOL for NP0081759 ((-)-3-Acetyl-khayalactone)

3D MOL for NP0081759 ((-)-3-Acetyl-khayalactone)

3D SDF for NP0081759 ((-)-3-Acetyl-khayalactone)

3D-SDF for NP0081759 ((-)-3-Acetyl-khayalactone)

PDB for NP0081759 ((-)-3-Acetyl-khayalactone)

3D PDB for NP0081759 ((-)-3-Acetyl-khayalactone)

SMILES for NP0081759 ((-)-3-Acetyl-khayalactone)

INCHI for NP0081759 ((-)-3-Acetyl-khayalactone)

Structure for NP0081759 ((-)-3-Acetyl-khayalactone)

3D Structure for NP0081759 ((-)-3-Acetyl-khayalactone)