NP-MRD: Showing NP-Card for Limonin (NP0048381)

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Record Information

Version

2.0

Created at

2022-03-17 20:55:35 UTC

Updated at

2024-09-03 04:19:12 UTC

NP-MRD ID

NP0048381

Natural Product DOI

https://doi.org/10.57994/1670

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Limonin

Description

Limonin, also known as evodin or citrolimonin, 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. Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Limonin is an extremely weak basic (essentially neutral) compound (based on its pKa). Limonin is a bitter tasting compound. Outside of the human body, Limonin has been detected, but not quantified in, several different foods, such as citrus, lemons, mandarin orange (clementine, tangerine), and sweet oranges. This could make limonin a potential biomarker for the consumption of these foods. Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds. Limonin reduces proliferation of colon cancer cells and has been tested as an anti-obesity agent in mice. Chemically, it is a member of the class of compounds known as furanolactones. Ongoing research programs are examining the effects of limonin in human diseases. Limonin is present in plants such as those of the Dictamnus genus. Neuroprotective effects of limonin have also been described. Limonin is found in Citrus aurantium, Citrus hanaju, Citrus junos, Citrus maxima, Citrus medica, Citrus sinensis, Citrus sudachi, Citrus trifoliata, Dictamnus albus, Dictamnus dasycarpus, Tetradium glabrifolium, Flacourtia jangomas, Glycosmis parva, Phellodendron amurense, Samadera bidwillii and Vepris louisii. Limonin was first documented in 1998 (PMID: 9619117). Citrus seed extracts reportedly have antiviral properties, inhibiting replication of retroviruses like HIV-1 and HTLV-I.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218112D          

 34 40  0  0  0  0            999 V2000
   -1.4527   -0.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -2.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -0.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060    0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    0.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7252   -1.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393   -0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113    0.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129    0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8214   -2.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -2.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699    1.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    1.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214   -0.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850   -1.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -2.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8103    2.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9822    2.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    2.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 30  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 29  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 28  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 12 27  2  0  0  0  0
 13 14  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  2  0  0  0  0
 26 31  2  0  0  0  0
 26 34  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END


  Mrv0541 02241218112D          

 34 40  0  0  0  0            999 V2000
   -1.4527   -0.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -2.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -1.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -0.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    0.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060   -0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060    0.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    0.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -0.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7252   -1.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2382   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393   -0.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113    0.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129    0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8214   -2.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -2.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699    1.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850    1.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214   -0.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6850   -1.3377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -2.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0647    2.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8103    2.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9822    2.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235    2.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  2 17  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 30  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 29  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 28  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 12 27  2  0  0  0  0
 13 14  1  0  0  0  0
 14 26  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  2  0  0  0  0
 26 31  2  0  0  0  0
 26 34  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3

> <INCHI_KEY>
KBDSLGBFQAGHBE-UHFFFAOYSA-N

> <FORMULA>
C26H30O8

> <MOLECULAR_WEIGHT>
470.5116

> <EXACT_MASS>
470.194067936

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
47.85702797281153

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
2.4571911409999982

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.606840669762278

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1218213499743066

> <JCHEM_POLAR_SURFACE_AREA>
104.57000000000001

> <JCHEM_REFRACTIVITY>
114.71920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
limonin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.712  -1.732   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.712  -3.273   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.379  -4.043   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.049  -3.273   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.049  -1.732   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.379  -0.964   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.279  -0.964   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.279   0.569   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.049   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.379   0.569   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.606  -1.729   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.931  -0.964   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.931   0.569   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.606   1.331   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.178  -1.254   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.087  -2.502   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.178  -3.753   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.567  -0.702   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.888   0.805   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.356   1.280   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.504   0.245   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.267  -4.842   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.780  -5.243   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.677   2.787   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.279   2.110   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.606   2.872   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.267  -1.735   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.279  -2.497   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.049  -0.191   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.286  -4.043   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.854   3.776   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.379   5.243   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.833   5.243   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.351   3.776   0.000  0.00  0.00           C+0
CONECT    1    2    6   15   18                                             
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6    7   29                                             
CONECT    6    1    5   10                                                  
CONECT    7    5    8   11   28                                             
CONECT    8    7    9   14   25                                             
CONECT    9    8   10                                                       
CONECT   10    6    9                                                       
CONECT   11    7   12   28                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14    8   13   26                                                  
CONECT   15    1   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17    2   16   22   23                                             
CONECT   18    1   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   15   20                                                       
CONECT   22   17                                                            
CONECT   23   17                                                            
CONECT   24   20                                                            
CONECT   25    8                                                            
CONECT   26   14   31   34                                                  
CONECT   27   12                                                            
CONECT   28    7   11                                                       
CONECT   29    5                                                            
CONECT   30    4                                                            
CONECT   31   26   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   26   33                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Value	Source
7,16-Dioxo-7,16-dideoxylimondiol	HMDB
Citrolimonin	HMDB
Dictamnolactone	HMDB
Evodia fruit	HMDB
Evodia fruit (JP15)	HMDB
Evodin	HMDB
Evodine?	HMDB
Limone?	HMDB
Limonoate D-ring-lactone	HMDB
Limonoic acid 3,19:16,17-dilactone	HMDB
Limonoic acid, di-delta-lactone	HMDB
Obaculactone	HMDB

Chemical Formula

C₂₆H₃₀O₈

Average Mass

470.5116 Da

Monoisotopic Mass

470.19407 Da

IUPAC Name

19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

Traditional Name

limonin

CAS Registry Number

1180-71-8

SMILES

CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

InChI Identifier

InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3

InChI Key

KBDSLGBFQAGHBE-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, C2D6OS, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	[email protected]	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus aurantium	LOTUS Database	35616633
Citrus hanaju	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus paradisi	FooDB	PHYTOHUB
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus sinensis	LOTUS Database	35616633
Citrus sudachi	LOTUS Database	35616633
Citrus trifoliata	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dictamnus albus	LOTUS Database	35616633
Dictamnus dasycarpus	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Flacourtia jangomas	LOTUS Database	35616633
Glycosmis parva	LOTUS Database	35616633
Phellodendron amurense	LOTUS Database	35616633
Samadera bidwillii	LOTUS Database	35616633
Vepris louisii	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
Steroid lactone
11-oxosteroid
Oxosteroid
2-oxosteroid
Steroid
Naphthopyran
Naphthalene
Delta valerolactone
Dioxepane
1,4-dioxepane
Delta_valerolactone
Pyran
Oxane
Dicarboxylic acid or derivatives
Tetrahydrofuran
Heteroaromatic compound
Furan
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (LIMONIN )

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	3.47	ALOGPS
logP	2.46	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.61	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.72 m³·mol⁻¹	ChemAxon
Polarizability	47.86 Å³	ChemAxon
Number of Rings	7	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

HMDB0035921

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Limonin

METLIN ID

Not Available

PubChem Compound

235284

PDB ID

Not Available

ChEBI ID

16226

Good Scents ID

Not Available

References

General References

Matsuda H, Yoshikawa M, Iinuma M, Kubo M: Antinociceptive and anti-inflammatory activities of limonin isolated from the fruits of Evodia rutaecarpa var. bodinieri. Planta Med. 1998 May;64(4):339-42. doi: 10.1055/s-2006-957447. [PubMed:9619117 ]

Showing NP-Card for Limonin (NP0048381)

MOL for NP0048381 (Limonin)

3D MOL for NP0048381 (Limonin)

3D SDF for NP0048381 (Limonin)

3D-SDF for NP0048381 (Limonin)

PDB for NP0048381 (Limonin)

3D PDB for NP0048381 (Limonin)

SMILES for NP0048381 (Limonin)

INCHI for NP0048381 (Limonin)

Structure for NP0048381 (Limonin)

3D Structure for NP0048381 (Limonin)