NP-MRD: Showing NP-Card for Mexicanolide (NP0076864)

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Record Information

Version

2.0

Created at

2022-04-28 22:03:21 UTC

Updated at

2022-04-28 22:03:21 UTC

NP-MRD ID

NP0076864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mexicanolide

Description

Mexicanolide 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. Mexicanolide is found in Cedrela graziovii, Cedrela mexicana , Cedrela odorata , Cipadessa baccifera, Ekebergia capensis , Khaya senegalensis , Swietenia mahagoni , Xylocarpus granatum and Xylocarpus moluccensis. Mexicanolide was first documented in 2021 (PMID: 33661631). Based on a literature review a small amount of articles have been published on Mexicanolide (PMID: 34730255) (PMID: 34581212) (PMID: 33882429).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200032D          

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M  END

     RDKit          3D

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M  END
> <DATABASE_ID>
NP0076864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)C(=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/C27H32O7/c1-25(2)19(12-20(28)32-5)27(4)17-6-8-26(3)18(15(17)10-16(22(25)30)23(27)31)11-21(29)34-24(26)14-7-9-33-13-14/h7,9,13,16-17,19,24H,6,8,10-12H2,1-5H3/t16-,17-,19-,24-,26+,27+/m0/s1

> <INCHI_KEY>
DNFJSIPZGYBGON-JCLAUGGVSA-N

> <FORMULA>
C27H32O7

> <MOLECULAR_WEIGHT>
468.546

> <EXACT_MASS>
468.21480337

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.704927850348724

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.956791359333333

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.339423597826462

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8888644810651187

> <JCHEM_POLAR_SURFACE_AREA>
99.88000000000001

> <JCHEM_REFRACTIVITY>
122.04679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S,5R,6R,13S,16S)-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,14,17-trioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-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       1.085   1.400   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.071   2.560   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.401   0.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.893  -1.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.273  -2.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.732  -1.631   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.416  -0.251   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.953  -0.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.806  -1.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.122  -2.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.585  -2.913   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.343  -1.338   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.027   0.042   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.174   1.324   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.857   2.704   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.637   1.227   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.196  -2.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.735  -2.683   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.150  -4.166   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.868  -5.019   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.660  -4.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.659  -2.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.924   1.208   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.544   1.892   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.907  -0.082   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.724   0.905   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.169  -3.660   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.267  -2.453   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.031  -3.964   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.488  -4.461   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.129  -4.977   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.831  -6.488   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.931   0.792   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.023  -0.567   0.000  0.00  0.00           C+0
CONECT    1    2    3   24                                                  
CONECT    2    1                                                            
CONECT    3    1    4   33   34                                             
CONECT    4    3    5   28                                                  
CONECT    5    4    6   25   27                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12   22                                             
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17   12   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22    9                                                            
CONECT   23    7   24                                                       
CONECT   24   23    1   25                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25                                                            
CONECT   27    5                                                            
CONECT   28    4   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₇

Average Mass

468.5460 Da

Monoisotopic Mass

468.21480 Da

IUPAC Name

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

Traditional Name

methyl [(1R,2S,5R,6R,13S,16S)-6-(furan-3-yl)-1,5,15,15-tetramethyl-8,14,17-trioxo-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[C@H]1C(C)(C)C(=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/C27H32O7/c1-25(2)19(12-20(28)32-5)27(4)17-6-8-26(3)18(15(17)10-16(22(25)30)23(27)31)11-21(29)34-24(26)14-7-9-33-13-14/h7,9,13,16-17,19,24H,6,8,10-12H2,1-5H3/t16-,17-,19-,24-,26+,27+/m0/s1

InChI Key

DNFJSIPZGYBGON-JCLAUGGVSA-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
Cedrela graziovii	Plant	KNApSAcK
Cedrela mexicana	Plant	KNApSAcK
Cedrela odorata	Plant	KNApSAcK
Cipadessa baccifera	LOTUS Database	35616633
Ekebergia capensis	Plant	KNApSAcK
Khaya senegalensis	Plant	KNApSAcK
Swietenia mahagoni	Plant	KNApSAcK
Xylocarpus granatum	LOTUS Database	35616633
Xylocarpus moluccensis	LOTUS Database	35616633

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
Delta valerolactone
Delta_valerolactone
1,3-diketone
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Pyran
Oxane
Furan
Heteroaromatic compound
Methyl ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.5	ALOGPS
logP	3.96	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.05 m³·mol⁻¹	ChemAxon
Polarizability	48.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00035024

Chemspider ID

10222034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bellone ML, Munoz Camero C, Chini MG, Dal Piaz F, Hernandez V, Bifulco G, De Tommasi N, Braca A: Limonoids from Guarea guidonia and Cedrela odorata: Heat Shock Protein 90 (Hsp90) Modulator Properties of Chisomicine D. J Nat Prod. 2021 Mar 26;84(3):724-737. doi: 10.1021/acs.jnatprod.0c01217. Epub 2021 Mar 4. [PubMed:33661631 ]
Vasquez-Ruiz V, Ramirez-Cisneros MA, Rios MY: Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and (1) H and (13) C NMR data. Magn Reson Chem. 2022 Mar;60(3):275-358. doi: 10.1002/mrc.5229. Epub 2021 Nov 21. [PubMed:34730255 ]
Jiang YH, Jiang TJ, Lv XF, Yu XF, Chi WQ: Antimicrobial mexicanolide limonoids from the seeds of Khaya senegalensis. J Asian Nat Prod Res. 2022 Jul;24(7):634-640. doi: 10.1080/10286020.2021.1972981. Epub 2021 Sep 28. [PubMed:34581212 ]
An FL, Sun DM, Wang RZ, Yang MH, Luo J, Kong LY: Corrigendum to "Trijugin- and mexicanolide-type limonoids from the fruits of Heynea trijuga that reverse multidrug resistance in MCF-7/DOX cells" [Phytochemistry 151 (2018) 42-49]. Phytochemistry. 2021 Jul;187:112777. doi: 10.1016/j.phytochem.2021.112777. Epub 2021 Apr 18. [PubMed:33882429 ]

Showing NP-Card for Mexicanolide (NP0076864)

MOL for NP0076864 (Mexicanolide)

3D MOL for NP0076864 (Mexicanolide)

3D SDF for NP0076864 (Mexicanolide)

3D-SDF for NP0076864 (Mexicanolide)

PDB for NP0076864 (Mexicanolide)

3D PDB for NP0076864 (Mexicanolide)

SMILES for NP0076864 (Mexicanolide)

INCHI for NP0076864 (Mexicanolide)

Structure for NP0076864 (Mexicanolide)

3D Structure for NP0076864 (Mexicanolide)