NP-MRD: Showing NP-Card for Linonin (NP0046574)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:08:08 UTC

Updated at

2022-03-17 20:08:08 UTC

NP-MRD ID

NP0046574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linonin

Description

Linonin, 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. Linonin is found in Atractylodes chinensis , Azadiractia indica, Citrus aurantium , Citrus bergania, Citrus depressa, Citrus hanaju, Citrus cavaleriei, Citrus junos , Citrus macrophylla, Citrus grandis , Citrus medica, Citrus reticulata , Citrus sinensis, Citrus sphaerocarpa, Citrus spp, Citrus spp., Citrus sudachi , Citrus sudachii, Citrus tamurana, Citrus tamurana Hort. , Citrus trifoliata, Citrus unshiu, Citrus unshiu Markovich , Clausena anisata, Coptis chinensis , Coptis deltoidea , Coptis teeta , Dictamnus albus, Dictamnus angustifolius, Dictamnus dasycarpus , Dictamnus radicis Cortex, Tetradium glabrifolium, Tetradium daniellii, Euodia rutaecarpa, Fagaropsis glabra, Flacourtia jangomas, Glycosmis parva, Limonia acidissima, Melia toosendan , Murraya paniculata, Oricia suaveolens, Phellodendron amurense, Phellodendron amurense var.wilsonii , Phellodendron chinense , Raulinoa echinata, Samadera bidwillii, Skimmia japonica, Tetradium trichotomum, Vepris louisii and Vepris suaveolens. Linonin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

limonin
  Mrv1572001071617152D          

 34 40  0  0  1  0            999 V2000
    7.4969    4.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6848    3.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6253    4.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9141    3.1888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2313    2.7258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1184    1.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543    1.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2414    0.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7029    2.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938    2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    3.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8603    4.0081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3284    4.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5163    4.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9845    5.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    3.7176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1765    4.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7678    3.0869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4875    2.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    2.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436    2.7965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8633    2.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315    2.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7997    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    4.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    4.6886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    4.2031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7042    4.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239    3.5724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0512    1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142    1.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    0.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587    1.6460    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  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 16 29  1  0  0  0  0
 21 29  1  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  6  0  0  0
 30 31  2  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
 30 34  1  0  0  0  0
M  END

limonin
  Mrv1572001071617152D          

 34 40  0  0  1  0            999 V2000
    7.4969    4.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6848    3.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6253    4.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9141    3.1888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2313    2.7258    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1184    1.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3543    1.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2414    0.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7029    2.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938    2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5800    3.2321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8603    4.0081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3284    4.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5163    4.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9845    5.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    3.7176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1765    4.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7678    3.0869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4875    2.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    2.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436    2.7965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8633    2.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315    2.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7997    3.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0800    4.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    4.6886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    4.2031    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7042    4.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239    3.5724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0512    1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142    1.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    0.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2319    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587    1.6460    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  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 29 28  1  1  0  0  0
 16 29  1  0  0  0  0
 21 29  1  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  6  0  0  0
 30 31  2  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
 30 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)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/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

> <INCHI_KEY>
KBDSLGBFQAGHBE-MSGMIQHVSA-N

> <FORMULA>
C26H30O8

> <MOLECULAR_WEIGHT>
470.518

> <EXACT_MASS>
470.194067926

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.806472840384515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,7S,10R,13R,14R,16S,19R,20S)-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>
-2.8525572165882376

> <JCHEM_POLAR_SURFACE_AREA>
104.57000000000001

> <JCHEM_REFRACTIVITY>
114.7192

> <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                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: limonin                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      13.994   7.703   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.478   7.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.367   8.968   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.906   5.952   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.632   5.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.421   3.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.995   2.982   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.784   1.457   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.779   3.927   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.948   5.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.416   6.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.939   7.482   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.946   8.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.430   8.388   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.438   9.565   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.907   6.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.796   8.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.900   5.762   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.377   4.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.861   4.043   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.868   5.220   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.345   3.772   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.352   4.949   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.359   6.126   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.883   7.575   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.890   8.752   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.399   7.846   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.915   8.117   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.391   6.668   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.829   3.501   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.693   2.226   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.748   1.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.300   1.533   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.350   3.073   0.000  0.00  0.00           C+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   29                                             
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   16   21   27                                             
CONECT   30   23   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
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	ChEBI
Citrolimonin	ChEBI
Dictamnolactone	ChEBI
Evodia fruit	ChEBI
Evodin	ChEBI
Limonoate D-ring-lactone	ChEBI
Limonoic acid 3,19:16,17-dilactone	ChEBI
Limonoic acid, di-delta-lactone	ChEBI
Obaculactone	ChEBI
Limonoic acid D-ring-lactone	Generator
Limonoate 3,19:16,17-dilactone	Generator
Limonoate, di-delta-lactone	Generator
Limonoate, di-δ-lactone	Generator
Limonoic acid, di-δ-lactone	Generator

Chemical Formula

C₂₆H₃₀O₈

Average Mass

470.5180 Da

Monoisotopic Mass

470.19407 Da

IUPAC Name

(1R,2R,7S,10R,13R,14R,16S,19R,20S)-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)O[C@H]2CC(=O)OC[C@@]22[C@H]1CC(=O)[C@]1(C)[C@@H]2CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)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/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1

InChI Key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Atractylodes chinensis	Plant	KNApSAcK
Azadiractia indica	-	KNApSAcK
Citrus aurantium	Plant	KNApSAcK
Citrus bergania	Plant	KNApSAcK
Citrus depressa	LOTUS Database	35616633
Citrus hanaju	LOTUS Database	35616633
Citrus ichangensis	LOTUS Database	35616633
Citrus junos	Plant	KNApSAcK
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus macrophylla	LOTUS Database	35616633
Citrus maxima	Plant	KNApSAcK
Citrus medica	LOTUS Database	35616633
Citrus paradisi	FooDB	PHYTOHUB
Citrus reticulata	Plant	KNApSAcK
Citrus sinensis	LOTUS Database	35616633
Citrus sphaerocarpa	LOTUS Database	35616633
Citrus spp	Plant	KNApSAcK
Citrus spp.	Plant	KNApSAcK
Citrus sudachi	Plant	KNApSAcK
Citrus sudachii	Plant	KNApSAcK
Citrus tamurana	LOTUS Database	35616633
Citrus tamurana Hort.	Plant	KNApSAcK
Citrus trifoliata	LOTUS Database	35616633
Citrus unshiu	LOTUS Database	35616633
Citrus unshiu Markovich	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	PHYTOHUB
Clausena anisata	LOTUS Database	35616633
Coptis chinensis	Plant	KNApSAcK
Coptis deltoidea	Plant	KNApSAcK
Coptis teeta	Plant	KNApSAcK
Dictamnus albus	LOTUS Database	35616633
Dictamnus angustifolius	Plant	KNApSAcK
Dictamnus dasycarpus	Plant	KNApSAcK
Dictamnus radicis Cortex	Plant	KNApSAcK
Euodia fargesii	LOTUS Database	35616633
Euodia hupehensis	LOTUS Database	35616633
Euodia rutaecarpa	Plant	KNApSAcK
Fagaropsis glabra	LOTUS Database	35616633
Flacourtia jangomas	LOTUS Database	35616633
Glycosmis parva	LOTUS Database	35616633
Limonia acidissima	LOTUS Database	35616633
Melia azedarach var. toosendan	Plant	KNApSAcK
Murraya paniculata	LOTUS Database	35616633
Oricia suaveolens	Plant	KNApSAcK
Phellodendron amurense	LOTUS Database	35616633
Phellodendron amurense var.wilsonii	Plant	KNApSAcK
Phellodendron chinense	Plant	KNApSAcK
Raulinoa echinata	LOTUS Database	35616633
Samadera bidwillii	LOTUS Database	35616633
Skimmia japonica	LOTUS Database	35616633
Tetradium trichotomum	LOTUS Database	35616633
Vepris louisii	LOTUS Database	35616633
Vepris suaveolens	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

epoxide (CHEBI:16226 )
organic heterohexacyclic compound (CHEBI:16226 )
furans (CHEBI:16226 )
lactone (CHEBI:16226 )
limonoid (CHEBI:16226 )
hexacyclic triterpenoid (CHEBI:16226 )
Limonoids (C03514 )

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)	-2.9	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	47.81 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005049

KNApSAcK ID

C00003719

Chemspider ID

Not Available

KEGG Compound ID

C03514

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Limonin

METLIN ID

Not Available

PubChem Compound

179651

PDB ID

Not Available

ChEBI ID

16226

Good Scents ID

Not Available

References

General References

Showing NP-Card for Linonin (NP0046574)

MOL for NP0046574 (Linonin)

3D MOL for NP0046574 (Linonin)

3D SDF for NP0046574 (Linonin)

3D-SDF for NP0046574 (Linonin)

PDB for NP0046574 (Linonin)

3D PDB for NP0046574 (Linonin)

SMILES for NP0046574 (Linonin)

INCHI for NP0046574 (Linonin)

Structure for NP0046574 (Linonin)

3D Structure for NP0046574 (Linonin)