NP-MRD: Showing NP-Card for (5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid (NP0158717)

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Record Information

Version

2.0

Created at

2022-09-02 16:21:10 UTC

Updated at

2022-09-02 16:21:10 UTC

NP-MRD ID

NP0158717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid

Description

Limonoate A-ring lactone, also known as limonoic acid a-ring lactone, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. (5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid is found in Citrus paradisi. (5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid was first documented in 2004 (PMID: 15464158). Based on a literature review a small amount of articles have been published on Limonoate A-ring lactone (PMID: 32483918) (PMID: 30347650) (PMID: 25652567) (PMID: 21681758).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218212D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022218212D          

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 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
 21 30  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2CC(=O)OCC22C1CC(=O)[C@]1(C)C2CC[C@](C)([C@@H](O)C2=COC=C2)C11OC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15)12-33-18(28)10-17(25)34-22)5-7-23(3,19(29)13-6-8-32-11-13)26(24)20(35-26)21(30)31/h6,8,11,14-15,17,19-20,29H,5,7,9-10,12H2,1-4H3,(H,30,31)/t14?,15?,17?,19-,20?,23+,24-,25?,26?/m0/s1

> <INCHI_KEY>
JQTDUZWQZNXSOU-XVBQGLHTSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.73655130924653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5'R,7'R)-5'-[(R)-(furan-3-yl)(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.7927200163333317

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.526393560539603

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.068636159846929

> <JCHEM_PKA_STRONGEST_BASIC>
-2.852280417081419

> <JCHEM_POLAR_SURFACE_AREA>
135.79999999999998

> <JCHEM_REFRACTIVITY>
118.2114

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5'R,7'R)-5'-[(R)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.021  -0.890   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.432  -0.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.788  -1.878   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.228   1.012   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.892   2.069   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.855   3.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.170   4.410   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.134   5.950   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.522   3.672   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.565   2.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.244   1.331   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.959  -0.182   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.128  -1.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.581  -0.675   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.749  -1.678   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.865   0.839   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.034  -0.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.696   1.842   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.981   3.355   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.434   3.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.602   2.863   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.043   2.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.387   4.188   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.632   5.530   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.927   4.170   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.846   5.406   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.305   4.914   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.288   3.374   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.818   2.914   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.318   1.349   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.832   1.065   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.829  -0.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.544  -1.617   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.320  -2.552   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       7.713  -2.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   18                                             
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   21   16   31   32                                             
CONECT   31   30   32                                                       
CONECT   32   31   30   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
Limonoic acid a-ring lactone	Generator

Chemical Formula

C₂₆H₃₂O₉

Average Mass

488.5330 Da

Monoisotopic Mass

488.20463 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)OC2CC(=O)OCC22C1CC(=O)[C@]1(C)C2CC[C@](C)([C@@H](O)C2=COC=C2)C11OC1C(O)=O

InChI Identifier

InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15)12-33-18(28)10-17(25)34-22)5-7-23(3,19(29)13-6-8-32-11-13)26(24)20(35-26)21(30)31/h6,8,11,14-15,17,19-20,29H,5,7,9-10,12H2,1-4H3,(H,30,31)/t14?,15?,17?,19-,20?,23+,24-,25?,26?/m0/s1

InChI Key

JQTDUZWQZNXSOU-XVBQGLHTSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Citrus paradisi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Heteroaromatic compound
Furan
Oxolane
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
Carbonyl group
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

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

101359991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cui Y, Allmon SD, Siegel JB: Functional characterization and reclassification of an enzyme previously proposed to be a limonoid UDP-glucosyltransferase. J Sci Food Agric. 2020 Oct;100(13):4870-4878. doi: 10.1002/jsfa.10547. Epub 2020 Jun 29. [PubMed:32483918 ]
Zhang J, Yang Z, Liang Y, Zhang L, Ling W, Guo C, Liang G, Luo G, Ye Q, Zhong B: Effects of Postharvest Time, Heat Treatment, pH and Filtration on the Limonin Content in Newhall Navel Orange (Citrus sinensis Osbeck cv. Newhall) Juice. Molecules. 2018 Oct 19;23(10):2691. doi: 10.3390/molecules23102691. [PubMed:30347650 ]
Arbona V, Iglesias DJ, Gomez-Cadenas A: Non-targeted metabolite profiling of citrus juices as a tool for variety discrimination and metabolite flow analysis. BMC Plant Biol. 2015 Feb 5;15:38. doi: 10.1186/s12870-015-0430-8. [PubMed:25652567 ]
Breksa AP 3rd, Kahn T, Zukas AA, Hidalgo MB, Yuen ML: Limonoid content of sour orange varieties. J Sci Food Agric. 2011 Aug 15;91(10):1789-94. doi: 10.1002/jsfa.4383. Epub 2011 Mar 29. [PubMed:21681758 ]
Zukas AA, Breksa AP 3rd, Manners GD: Isolation and characterization of limonoate and nomilinoate A-ring lactones. Phytochemistry. 2004 Oct;65(19):2705-9. doi: 10.1016/j.phytochem.2004.08.016. [PubMed:15464158 ]
LOTUS database [Link]

Showing NP-Card for (5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid (NP0158717)

MOL for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

3D MOL for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

3D SDF for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

3D-SDF for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

PDB for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

3D PDB for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

SMILES for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

INCHI for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

Structure for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)

3D Structure for NP0158717 ((5'r,7'r)-5'-[(s)-furan-3-yl(hydroxy)methyl]-5',7',11',11'-tetramethyl-8',15'-dioxo-12',16'-dioxaspiro[oxirane-2,6'-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid)