NP-MRD: Showing NP-Card for (-)-Khayalactol (NP0080677)

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Record Information

Version

2.0

Created at

2022-04-29 01:40:39 UTC

Updated at

2022-04-29 01:40:39 UTC

NP-MRD ID

NP0080677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Khayalactol

Description

Khayalactol 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. (-)-Khayalactol is found in Khaya ivorensis and Khaya senegalensis . (-)-Khayalactol was first documented in 2004 (PMID: 14971689). Based on a literature review very few articles have been published on Khayalactol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203402D          

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M  END

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 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 14 26  1  1  0  0  0
 10 27  1  1  0  0  0
  6 27  1  0  0  0  0
  6 28  1  1  0  0  0
  5 29  1  1  0  0  0
  4 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  1  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](O)[C@@H]1[C@@]2(C)[C@H]3CC[C@]4(C)[C@@H](CC(=O)O[C@H]4C4=COC=C4)[C@@]33C[C@@](O)(C(=O)C1(C)C)[C@]2(O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O10/c1-22(2)18(17(29)20(30)34-5)24(4)14-6-8-23(3)15(10-16(28)36-19(23)13-7-9-35-11-13)25(14)12-26(32,21(22)31)27(24,33)37-25/h7,9,11,14-15,17-19,29,32-33H,6,8,10,12H2,1-5H3/t14-,15-,17+,18+,19+,23-,24-,25-,26-,27-/m1/s1

> <INCHI_KEY>
GQSKLPDTOGRXHH-PPIMSCDMSA-N

> <FORMULA>
C27H34O10

> <MOLECULAR_WEIGHT>
518.559

> <EXACT_MASS>
518.215197295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.15872041899625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-2-[(1S,2R,6R,7R,10R,11S,12S,15R,16R)-6-(furan-3-yl)-15,16-dihydroxy-7,11,13,13-tetramethyl-4,14-dioxo-5,17-dioxapentacyclo[13.2.1.0^{1,10}.0^{2,7}.0^{11,16}]octadecan-12-yl]-2-hydroxyacetate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.6858625016666653

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.888566709429956

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.394779408391594

> <JCHEM_PKA_STRONGEST_BASIC>
-2.875846762615103

> <JCHEM_POLAR_SURFACE_AREA>
152.73

> <JCHEM_REFRACTIVITY>
124.3368

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-(methyl [(1S,2R,6R,7R,10R,11S,12S,15R,16R)-6-(furan-3-yl)-15,16-dihydroxy-7,11,13,13-tetramethyl-4,14-dioxo-5,17-dioxapentacyclo[13.2.1.0^{1,10}.0^{2,7}.0^{11,16}]octadecan-12-yl](hydroxy)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      -0.762  -0.324   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.930   0.679   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.116  -1.878   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.056  -2.879   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.495  -2.276   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.654  -0.786   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.802   0.293   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.266   1.736   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.383   0.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.578  -0.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.953  -2.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.533  -3.876   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.059  -3.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.901  -2.606   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.193  -1.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.023   0.059   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.561  -0.012   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.392   1.286   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.269  -1.379   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.439  -2.676   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.147  -4.044   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.670  -4.275   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.921  -5.794   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.553  -6.502   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.457  -5.420   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.607  -3.974   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.193   0.206   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.174  -1.213   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.719  -3.800   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.182  -4.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.017  -5.367   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.454  -4.812   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.779  -6.888   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.978  -7.855   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.618  -4.955   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.633  -1.613   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.174  -2.998   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   36   37                                             
CONECT    4    3    5   30                                                  
CONECT    5    4    6   11   29                                             
CONECT    6    5    7   27   28                                             
CONECT    7    6    1    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   15   27                                             
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20   26                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26   14                                                            
CONECT   27   10    6                                                       
CONECT   28    6                                                            
CONECT   29    5                                                            
CONECT   30    4   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₀

Average Mass

518.5590 Da

Monoisotopic Mass

518.21520 Da

IUPAC Name

methyl (2S)-2-[(1S,2R,6R,7R,10R,11S,12S,15R,16R)-6-(furan-3-yl)-15,16-dihydroxy-7,11,13,13-tetramethyl-4,14-dioxo-5,17-dioxapentacyclo[13.2.1.0^{1,10}.0^{2,7}.0^{11,16}]octadecan-12-yl]-2-hydroxyacetate

Traditional Name

(S)-(methyl [(1S,2R,6R,7R,10R,11S,12S,15R,16R)-6-(furan-3-yl)-15,16-dihydroxy-7,11,13,13-tetramethyl-4,14-dioxo-5,17-dioxapentacyclo[13.2.1.0^{1,10}.0^{2,7}.0^{11,16}]octadecan-12-yl](hydroxy)acetate)

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](O)[C@@H]1[C@@]2(C)[C@H]3CC[C@]4(C)[C@@H](CC(=O)O[C@H]4C4=COC=C4)[C@@]33C[C@@](O)(C(=O)C1(C)C)[C@]2(O)O3

InChI Identifier

InChI=1S/C27H34O10/c1-22(2)18(17(29)20(30)34-5)24(4)14-6-8-23(3)15(10-16(28)36-19(23)13-7-9-35-11-13)25(14)12-26(32,21(22)31)27(24,33)37-25/h7,9,11,14-15,17-19,29,32-33H,6,8,10,12H2,1-5H3/t14-,15-,17+,18+,19+,23-,24-,25-,26-,27-/m1/s1

InChI Key

GQSKLPDTOGRXHH-PPIMSCDMSA-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
Khaya senegalensis	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
Steroid lactone
12-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
Steroid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.65	ALOGPS
logP	1.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.39	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	152.73 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	124.34 m³·mol⁻¹	ChemAxon
Polarizability	52.16 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046060

Chemspider ID

8801106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10625743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Aswad AF, Abdelgaleil SA, Nakatani M: Feeding deterrent and growth inhibitory properties of limonoids from Khaya senegalensis against the cotton leafworm, Spodoptera littoralis. Pest Manag Sci. 2004 Feb;60(2):199-203. doi: 10.1002/ps.818. [PubMed:14971689 ]

Showing NP-Card for (-)-Khayalactol (NP0080677)

MOL for NP0080677 ((-)-Khayalactol)

3D MOL for NP0080677 ((-)-Khayalactol)

3D SDF for NP0080677 ((-)-Khayalactol)

3D-SDF for NP0080677 ((-)-Khayalactol)

PDB for NP0080677 ((-)-Khayalactol)

3D PDB for NP0080677 ((-)-Khayalactol)

SMILES for NP0080677 ((-)-Khayalactol)

INCHI for NP0080677 ((-)-Khayalactol)

Structure for NP0080677 ((-)-Khayalactol)

3D Structure for NP0080677 ((-)-Khayalactol)