MiMeDB: Showing metabocard for CJ-15,183 (MMDBc0016915)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 07:25:51 UTC

Update Date

2025-10-07 16:06:36 UTC

Metabolite ID

MMDBc0016915

Metabolite Identification

Common Name

CJ-15,183

Description

CJ-15,183 is a squalene synthase inhibitor belonging to the class of organic compounds known as terpenoids. Its chemical structure features a unique arrangement of carbon atoms that allows it to effectively inhibit the enzyme squalene synthase, which plays a critical role in the biosynthetic pathway of sterols and triterpenes. This inhibition can disrupt the synthesis of squalene, a key precursor in the production of cholesterol and other important biomolecules. CJ-15,183 was isolated from the fermentation broth of the fungus Aspergillus aculeatus, highlighting the potential of fungal metabolites in drug discovery. The compound's mechanism of action involves targeting the squalene synthase enzyme, thereby influencing lipid metabolism and potentially impacting various biological pathways related to cholesterol homeostasis and membrane integrity. The identification of CJ-15,183 as a novel squalene synthase inhibitor underscores its relevance in the study of metabolic pathways and its potential therapeutic applications. (PMID:11827032 )

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152109252D          

 47 47  0  0  0  0            999 V2000
   -9.2928    4.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7777    4.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4422    3.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9271    2.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5915    1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0765    1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7409    0.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9204    0.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5849   -0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7644   -0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2795    0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4590    0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234   -0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -1.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -3.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674   -1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -2.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -4.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722   -2.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8279   -2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472   -2.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -2.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472   -0.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -3.5658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722   -3.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -2.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222   -2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8969    1.3471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2258   -0.1602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0698   -1.0001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4288   -1.1726    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6083   -1.2588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8180   -0.0102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 19  1  0  0  0  0
 24 19  1  0  0  0  0
 25 23  1  0  0  0  0
 26 20  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
 28 27  1  0  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 32 22  1  0  0  0  0
 33 24  2  0  0  0  0
 34 24  1  0  0  0  0
 35 25  2  0  0  0  0
 36 25  1  0  0  0  0
 37 26  2  0  0  0  0
 38 27  2  0  0  0  0
 39 28  1  0  0  0  0
 40 18  1  0  0  0  0
 40 26  1  0  0  0  0
 41 23  1  0  0  0  0
 41 27  1  0  0  0  0
 42  6  1  0  0  0  0
 43  7  1  0  0  0  0
 44  9  1  0  0  0  0
 45 10  1  0  0  0  0
 46 13  1  0  0  0  0
 47 14  1  0  0  0  0
M  END


  Mrv1652305152109252D          

 47 47  0  0  0  0            999 V2000
   -9.2928    4.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7777    4.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4422    3.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9271    2.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5915    1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0765    1.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7409    0.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9204    0.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5849   -0.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7644   -0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2795    0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4590    0.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234   -0.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029   -0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1604   -1.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -3.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674   -1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -2.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -4.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722   -2.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222   -0.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8279   -2.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472   -2.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -2.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -4.4858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847   -2.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528   -2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9472   -0.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7097    0.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -3.5658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7722   -3.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -2.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1222   -2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8969    1.3471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2258   -0.1602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0698   -1.0001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4288   -1.1726    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6083   -1.2588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8180   -0.0102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 19  1  0  0  0  0
 24 19  1  0  0  0  0
 25 23  1  0  0  0  0
 26 20  1  0  0  0  0
 28 17  1  0  0  0  0
 28 20  1  0  0  0  0
 28 27  1  0  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 32 22  1  0  0  0  0
 33 24  2  0  0  0  0
 34 24  1  0  0  0  0
 35 25  2  0  0  0  0
 36 25  1  0  0  0  0
 37 26  2  0  0  0  0
 38 27  2  0  0  0  0
 39 28  1  0  0  0  0
 40 18  1  0  0  0  0
 40 26  1  0  0  0  0
 41 23  1  0  0  0  0
 41 27  1  0  0  0  0
 42  6  1  0  0  0  0
 43  7  1  0  0  0  0
 44  9  1  0  0  0  0
 45 10  1  0  0  0  0
 46 13  1  0  0  0  0
 47 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016915

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CC\C([H])=C(/[H])C1CC(C(=O)O1)C(O)(CC(O)=O)C(=O)OC(C(CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O13/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-20(26(37)40-18)28(39,17-22(31)32)27(38)41-23(25(35)36)19(24(33)34)16-21(29)30/h6-7,9-10,13-14,18-20,23,39H,2-5,8,11-12,15-17H2,1H3,(H,29,30)(H,31,32)(H,33,34)(H,35,36)/b7-6-,10-9-,14-13+

> <INCHI_KEY>
SCNKZRBYVALSHS-OXXZWVFOSA-N

> <FORMULA>
C28H38O13

> <MOLECULAR_WEIGHT>
582.599

> <EXACT_MASS>
582.231241284

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.695203046461

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(3-carboxy-2-hydroxy-2-{2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]oxolan-3-yl}propanoyl)oxy]propane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
3.4548667639999993

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.4251327724880167

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8454186812891544

> <JCHEM_PKA_STRONGEST_BASIC>
-4.272979732233659

> <JCHEM_POLAR_SURFACE_AREA>
222.03

> <JCHEM_REFRACTIVITY>
142.81040000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3-carboxy-2-hydroxy-2-{2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]oxolan-3-yl}propanoyl)oxy]propane-1,2,3-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -17.347   8.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -18.252   7.659   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.625   6.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -18.531   5.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -17.904   3.600   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.809   2.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -18.183   0.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.651   0.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.025  -0.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.494  -0.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.588   0.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.057   0.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.430  -1.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.899  -1.265   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.766  -2.992   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.881  -1.292   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.938  -6.064   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.272  -2.672   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.651  -2.626   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.605  -4.524   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.659  -1.292   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.938  -7.604   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.191  -2.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.881  -3.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.961  -1.292   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.012  -5.150   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.501  -3.960   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.271  -5.294   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.429   0.041   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.429  -2.626   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -3.604  -8.374   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.271  -8.374   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.651  -5.294   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.659  -3.960   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.501  -1.292   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.191   0.041   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -9.332  -6.656   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -6.271  -2.626   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -7.041  -6.627   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -10.042  -4.005   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -3.961  -3.960   0.000  0.00  0.00           O+0
HETATM   42  H   UNK     0     -20.341   2.515   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0     -19.088  -0.299   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0     -16.930  -1.867   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0     -13.867  -2.189   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0     -12.336  -2.350   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.994  -0.019   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   44                                                  
CONECT   10    9   11   45                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   46                                                  
CONECT   14   13   18   47                                                  
CONECT   15   18   20                                                       
CONECT   16   19   21                                                       
CONECT   17   22   28                                                       
CONECT   18   14   15   40                                                  
CONECT   19   16   23   24                                                  
CONECT   20   15   26   28                                                  
CONECT   21   16   29   30                                                  
CONECT   22   17   31   32                                                  
CONECT   23   19   25   41                                                  
CONECT   24   19   33   34                                                  
CONECT   25   23   35   36                                                  
CONECT   26   20   37   40                                                  
CONECT   27   28   38   41                                                  
CONECT   28   17   20   27   39                                             
CONECT   29   21                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   22                                                            
CONECT   33   24                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   25                                                            
CONECT   37   26                                                            
CONECT   38   27                                                            
CONECT   39   28                                                            
CONECT   40   18   26                                                       
CONECT   41   23   27                                                       
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
MASTER        0    0    0    0    0    0    0    0   47    0   94    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₃₈O₁₃

Average Mass

582.599

Monoisotopic Mass

582.231241284

IUPAC Name

1-[(3-carboxy-2-hydroxy-2-{2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]oxolan-3-yl}propanoyl)oxy]propane-1,2,3-tricarboxylic acid

Traditional Name

1-[(3-carboxy-2-hydroxy-2-{2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]oxolan-3-yl}propanoyl)oxy]propane-1,2,3-tricarboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CC\C([H])=C(/[H])C1CC(C(=O)O1)C(O)(CC(O)=O)C(=O)OC(C(CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C28H38O13/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-20(26(37)40-18)28(39,17-22(31)32)27(38)41-23(25(35)36)19(24(33)34)16-21(29)30/h6-7,9-10,13-14,18-20,23,39H,2-5,8,11-12,15-17H2,1H3,(H,29,30)(H,31,32)(H,33,34)(H,35,36)/b7-6-,10-9-,14-13+

InChI Key

SCNKZRBYVALSHS-OXXZWVFOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Monosaccharide
Tertiary alcohol
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0036 g/L	ALOGPS
logP	2.39	ALOGPS
logP	3.45	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	222.03 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	142.81 m³·mol⁻¹	ChemAxon
Polarizability	58.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8070255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9894585

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for CJ-15,183 (MMDBc0016915)

MOL for #<Metabolite:0x00007f8dbc259828>

3D MOL for #<Metabolite:0x00007f8dbc259828>

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3D Structure for #<Metabolite:0x00007f8dbc259828>