Np mrd loader

Showing NP-Card for Elaterinide (NP0048373)

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Record Information
Version1.0
Created at2022-03-17 20:55:28 UTC
Updated at2022-03-17 20:55:28 UTC
NP-MRD IDNP0048373
Secondary Accession NumbersNone
Natural Product Identification
Common NameElaterinide
DescriptionElaterinide, also known as colocynthin or coloside a, belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Elaterinide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, elaterinide has been detected, but not quantified in, fruits and watermelons. Elaterinide is found in Citrullus colocynthis, Citrullus colocynthis (L.) and Iberis amara. It was first documented in 2000 (PMID: 11413487). This could make elaterinide a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048373 (Elaterinide)


  Mrv0541 05061308462D          

 51 55  0  0  0  0            999 V2000
   11.8344   -0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7762   -0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641   -2.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6284   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0886   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0718    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0172   -0.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9436    1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503    0.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9821    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8890    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -1.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5108   -1.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9362   -1.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327    1.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.8721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7063   -0.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
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 50 23  1  0  0  0  0
 50 32  1  0  0  0  0
 51 18  1  0  0  0  0
 51 33  1  0  0  0  0
M  END
Download

3D MOL for NP0048373 (Elaterinide)

Download
3D SDF for NP0048373 (Elaterinide)

  Mrv0541 05061308462D          

 51 55  0  0  0  0            999 V2000
   11.8344   -0.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0019    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7762   -0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8641   -2.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6284   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4662    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0886   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0718    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0172   -0.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9436    1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421    0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503    0.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8890    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373    0.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2027   -1.5511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5108   -1.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9362   -1.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6327    1.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2306    0.8721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7306    1.6978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7859    0.8867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.4364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -0.4847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7063   -0.0710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 13 12  2  0  0  0  0
 18  1  1  0  0  0  0
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 20 19  1  0  0  0  0
 21 15  1  0  0  0  0
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 33  3  1  0  0  0  0
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 34  5  1  0  0  0  0
 34 19  1  0  0  0  0
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 38  9  1  0  0  0  0
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 38 30  1  0  0  0  0
 39 17  1  0  0  0  0
 40 18  2  0  0  0  0
 41 21  1  0  0  0  0
 42 25  2  0  0  0  0
 43 26  2  0  0  0  0
 44 27  1  0  0  0  0
 45 28  1  0  0  0  0
 46 29  1  0  0  0  0
 47 31  2  0  0  0  0
 48 38  1  0  0  0  0
 49 22  1  0  0  0  0
 49 32  1  0  0  0  0
 50 23  1  0  0  0  0
 50 32  1  0  0  0  0
 51 18  1  0  0  0  0
 51 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+

> <INCHI_KEY>
QKEJRKXVLGOJMB-OUKQBFOZSA-N

> <FORMULA>
C38H54O13

> <MOLECULAR_WEIGHT>
718.8276

> <EXACT_MASS>
718.356441814

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
76.54239287155482

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
1.1821819683333317

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.82184007132371

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.127820176701315

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883865699538827

> <JCHEM_POLAR_SURFACE_AREA>
217.34999999999994

> <JCHEM_REFRACTIVITY>
185.0251

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048373 (Elaterinide)
Download
PDB for NP0048373 (Elaterinide)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      22.091  -1.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.670   1.604   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.249  -1.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.342  -4.434   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.480  -3.762   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.506  -3.399   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.070   0.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.374   0.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.099  -0.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.320  -3.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.836  -3.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.354   1.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.934   0.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.858  -0.092   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.091  -2.849   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.406   0.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.729  -2.624   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.565  -1.559   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.327  -2.717   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.851  -1.269   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.366  -1.985   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.342  -0.363   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206  -1.176   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.359  -2.175   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.828   1.926   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.890   0.451   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.199   0.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.675   1.450   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.841   1.721   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.938  -0.506   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.819  -1.811   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.833   0.544   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.459   0.078   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.812  -2.988   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.875  -1.904   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.399  -0.456   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.367  -0.998   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.883   0.710   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.245  -2.895   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      19.620  -2.775   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.814  -2.508   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      14.248   3.352   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       7.897   1.628   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -2.715  -0.270   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -1.668   2.627   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.364   3.169   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.303  -2.082   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      12.667   1.655   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.349   0.815   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       1.310  -0.905   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      19.985  -0.133   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   33                                                            
CONECT    3   33                                                            
CONECT    4   34                                                            
CONECT    5   34                                                            
CONECT    6   35                                                            
CONECT    7   36                                                            
CONECT    8   37                                                            
CONECT    9   38                                                            
CONECT   10   11   19                                                       
CONECT   11   10   24                                                       
CONECT   12   13   25                                                       
CONECT   13   12   33                                                       
CONECT   14   20   22                                                       
CONECT   15   21   35                                                       
CONECT   16   26   36                                                       
CONECT   17   23   39                                                       
CONECT   18    1   40   51                                                  
CONECT   19   10   20   34                                                  
CONECT   20   14   19   37                                                  
CONECT   21   15   30   41                                                  
CONECT   22   14   31   49                                                  
CONECT   23   17   27   50                                                  
CONECT   24   11   35   37                                                  
CONECT   25   12   38   42                                                  
CONECT   26   16   37   43                                                  
CONECT   27   23   28   44                                                  
CONECT   28   27   29   45                                                  
CONECT   29   28   32   46                                                  
CONECT   30   21   36   38                                                  
CONECT   31   22   34   47                                                  
CONECT   32   29   49   50                                                  
CONECT   33    2    3   13   51                                             
CONECT   34    4    5   19   31                                             
CONECT   35    6   15   24   36                                             
CONECT   36    7   16   30   35                                             
CONECT   37    8   20   24   26                                             
CONECT   38    9   25   30   48                                             
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   21                                                            
CONECT   42   25                                                            
CONECT   43   26                                                            
CONECT   44   27                                                            
CONECT   45   28                                                            
CONECT   46   29                                                            
CONECT   47   31                                                            
CONECT   48   38                                                            
CONECT   49   22   32                                                       
CONECT   50   23   32                                                       
CONECT   51   18   33                                                       
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

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3D PDB for NP0048373 (Elaterinide)
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SMILES for NP0048373 (Elaterinide)
CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C
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INCHI for NP0048373 (Elaterinide)
InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+
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Synonyms
ValueSource
alpha-Elaterin 2-D-glucopyranosideHMDB
beta-Glucoside de la curcurbitaine (e)HMDB
ColocynthinHMDB
Coloside aHMDB
Cucurbitacin e 2-O-beta-D-glucopyranosideHMDB
Cucurbitacin e-2-O-glucosideHMDB
CUEGHMDB
Elaterin, 2-beta-glucopyranosideHMDB
GratiotoxinHMDB
2-O-beta-D-Glycopyranosyl-cucurbitacin eHMDB
(3E)-6-Hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetic acidGenerator
ElaterinideMeSH
Chemical FormulaC38H54O13
Average Mass718.8276 Da
Monoisotopic Mass718.35644 Da
IUPAC Name(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Name(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
CAS Registry Number1398-78-3
SMILES
CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI Identifier
InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+
InChI KeyQKEJRKXVLGOJMB-OUKQBFOZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrullus colocynthisLOTUS Database
Citrullus colocynthis (L.)Plant
Citrullus lanatusFooDB
Iberis amaraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.28ALOGPS
logP1.18ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.13ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area217.35 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity185.03 m³·mol⁻¹ChemAxon
Polarizability76.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0035893  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014678  
KNApSAcK IDC00030029  
Chemspider ID4740095  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5901827  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]