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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:04:27 UTC

Update Date

2022-03-07 02:53:41 UTC

HMDB ID

HMDB0033358

Secondary Accession Numbers

HMDB33358

Metabolite Identification

Common Name

(S)-Neolitsine

Description

(E)-2-Tetracosenoic acid, also known as (e)-2-tetracosenoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms (E)-2-Tetracosenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033358
     RDKit          3D
(S)-Neolitsine
 41 46  0  0  0  0  0  0  0  0999 V2000
   -2.0375   -2.4891    0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734   -1.9202   -0.7716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840   -1.3578   -0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    0.0596   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    0.6635    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    1.7478    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    2.3417    1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562    1.8478    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    0.7441    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    0.1677   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9771   -1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403   -1.6530   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515   -0.9667   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -1.5358   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.9473   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.1611    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687    0.7223    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060    0.1553   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.5005    0.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8043   -0.2370   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -1.2815   -0.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    2.6438    1.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1342    3.8610    2.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.4287    2.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -3.5303    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180   -2.5760    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.8857    1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302   -1.5212   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450   -1.9757   -0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.6622   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5505    0.2039    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094    2.1673    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -0.5556   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089   -1.7457   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0763   -2.7010   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -2.4011   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.5797    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    0.3916   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -0.6132    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    4.5462    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624    4.2754    3.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21 15  1  0
 24  7  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv0541 05061307042D          

 24 29  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  5  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  1  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 22 15  1  0  0  0  0
 23  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24  9  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033358

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO4/c1-20-3-2-10-5-16-19(24-9-23-16)18-12-7-15-14(21-8-22-15)6-11(12)4-13(20)17(10)18/h5-7,13H,2-4,8-9H2,1H3

> <INCHI_KEY>
GKEOKAJRKHTDOS-UHFFFAOYSA-N

> <FORMULA>
C19H17NO4

> <MOLECULAR_WEIGHT>
323.3426

> <EXACT_MASS>
323.115758037

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.524754065954056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
2.947878963

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.034299002519812

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
87.56009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033358
     RDKit          3D
(S)-Neolitsine
 41 46  0  0  0  0  0  0  0  0999 V2000
   -2.0375   -2.4891    0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734   -1.9202   -0.7716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840   -1.3578   -0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    0.0596   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    0.6635    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    1.7478    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    2.3417    1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562    1.8478    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    0.7441    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    0.1677   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9771   -1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403   -1.6530   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515   -0.9667   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -1.5358   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.9473   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.1611    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687    0.7223    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060    0.1553   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.5005    0.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8043   -0.2370   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -1.2815   -0.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    2.6438    1.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1342    3.8610    2.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.4287    2.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -3.5303    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180   -2.5760    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.8857    1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302   -1.5212   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450   -1.9757   -0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.6622   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5505    0.2039    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094    2.1673    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -0.5556   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089   -1.7457   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0763   -2.7010   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -2.4011   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.5797    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    0.3916   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -0.6132    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    4.5462    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624    4.2754    3.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21 15  1  0
 24  7  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
M  END

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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.705  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      10.800  -2.786   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.800  -0.294   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3   10                                                       
CONECT    3    2   20                                                       
CONECT    4   11   13                                                       
CONECT    5   10   16                                                       
CONECT    6   11   14                                                       
CONECT    7   12   15                                                       
CONECT    8   21   22                                                       
CONECT    9   23   24                                                       
CONECT   10    2    5   17                                                  
CONECT   11    4    6   12                                                  
CONECT   12    7   11   18                                                  
CONECT   13    4   17   20                                                  
CONECT   14    6   15   21                                                  
CONECT   15    7   14   22                                                  
CONECT   16    5   19   23                                                  
CONECT   17   10   13   18                                                  
CONECT   18   12   17   19                                                  
CONECT   19   16   18   24                                                  
CONECT   20    1    3   13                                                  
CONECT   21    8   14                                                       
CONECT   22    8   15                                                       
CONECT   23    9   16                                                       
CONECT   24    9   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

COMPND    HMDB0033358
HETATM    1  C1  UNL     1      -2.038  -2.489   0.536  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.273  -1.920  -0.772  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.584  -1.358  -0.856  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.722   0.060  -0.414  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.489   0.664   0.110  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.552   1.748   0.954  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.421   2.342   1.472  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.156   1.848   1.148  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.095   0.744   0.290  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.222   0.168  -0.216  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.239  -0.977  -1.155  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.040  -1.653  -1.388  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.252  -0.967  -0.875  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.485  -1.536  -1.246  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.633  -0.947  -0.771  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.605   0.161   0.042  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.369   0.722   0.406  1.00  0.00           C  
HETATM   18  C17 UNL     1       1.206   0.155  -0.055  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.913   0.501   0.341  1.00  0.00           O  
HETATM   20  C18 UNL     1       5.804  -0.237  -0.484  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.984  -1.281  -0.965  1.00  0.00           O  
HETATM   22  O3  UNL     1       0.758   2.644   1.814  1.00  0.00           O  
HETATM   23  C19 UNL     1       0.134   3.861   2.179  1.00  0.00           C  
HETATM   24  O4  UNL     1      -1.204   3.429   2.331  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.646  -3.530   0.422  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.018  -2.576   1.047  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.321  -1.886   1.126  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.030  -1.521  -1.877  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.245  -1.976  -0.179  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.053   0.662  -1.308  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.550   0.204   0.332  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.509   2.167   1.236  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.611  -0.556  -2.143  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.209  -1.746  -2.507  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.076  -2.701  -0.943  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.498  -2.401  -1.880  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.387   1.580   1.035  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.210   0.392  -1.312  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.677  -0.613   0.085  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.176   4.546   1.325  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.562   4.275   3.115  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   11
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6    6   10
CONECT    6    7   32
CONECT    7    8    8   24
CONECT    8    9   22
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   12   33
CONECT   12   13   34   35
CONECT   13   14   14   18
CONECT   14   15   36
CONECT   15   16   16   21
CONECT   16   17   19
CONECT   17   18   18   37
CONECT   19   20
CONECT   20   21   38   39
CONECT   22   23
CONECT   23   24   40   41
END

HMDB0033358
     RDKit          3D
(S)-Neolitsine
 41 46  0  0  0  0  0  0  0  0999 V2000
   -2.0375   -2.4891    0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2734   -1.9202   -0.7716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840   -1.3578   -0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    0.0596   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4887    0.6635    0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523    1.7478    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209    2.3417    1.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562    1.8478    1.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    0.7441    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223    0.1677   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.9771   -1.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403   -1.6530   -1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515   -0.9667   -0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4855   -1.5358   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327   -0.9473   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    0.1611    0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687    0.7223    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060    0.1553   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9128    0.5005    0.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8043   -0.2370   -0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -1.2815   -0.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7583    2.6438    1.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1342    3.8610    2.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.4287    2.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -3.5303    0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180   -2.5760    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -1.8857    1.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0302   -1.5212   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2450   -1.9757   -0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533    0.6622   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5505    0.2039    0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094    2.1673    1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6112   -0.5556   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089   -1.7457   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0763   -2.7010   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -2.4011   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.5797    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    0.3916   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6773   -0.6132    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    4.5462    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5624    4.2754    3.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21 15  1  0
 24  7  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2-Tetracosenoate	Generator
Tetracosenoic acid	HMDB
Tetracosenoic acid, (Z)-isomer	HMDB
Neolitsine	HMDB

Chemical Formula

C₁₉H₁₇NO₄

Average Molecular Weight

323.3426

Monoisotopic Molecular Weight

323.115758037

IUPAC Name

13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

Traditional Name

13-methyl-5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene

CAS Registry Number

2466-42-4

SMILES

CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C19H17NO4/c1-20-3-2-10-5-16-19(24-9-23-16)18-12-7-15-14(21-8-22-15)6-11(12)4-13(20)17(10)18/h5-7,13H,2-4,8-9H2,1H3

InChI Key

GKEOKAJRKHTDOS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033358)
Cytoplasm (HMDB: HMDB0033358)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033358)

Source

Exogenous

Food

Food (HMDB: HMDB0033358)

Tea

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033358)

Not Available

Nutrient (HMDB: HMDB0033358)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	149 - 150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.49	ALOGPS
logP	2.95	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	7.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.56 m³·mol⁻¹	ChemAxon
Polarizability	34.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.39	31661259
DarkChem	[M-H]-	173.063	31661259
DeepCCS	[M-2H]-	201.387	30932474
DeepCCS	[M+Na]+	176.614	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	183.0	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	180.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Neolitsine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(OCO2)C=C31	4134.0	Standard polar	33892256
(S)-Neolitsine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(OCO2)C=C31	2670.7	Standard non polar	33892256
(S)-Neolitsine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(OCO2)C=C31	2979.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Neolitsine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-0093000000-0de08ca44a720073b9eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Neolitsine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 10V, Positive-QTOF	splash10-00di-0029000000-8ec1878d06cc8c9d039a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 20V, Positive-QTOF	splash10-00dl-0097000000-c0e0951dc05cf21108b9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 40V, Positive-QTOF	splash10-01ot-0090000000-8e527a1f91a7990a4474	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 10V, Negative-QTOF	splash10-00di-0019000000-7cf609f39fb9a5f45042	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 20V, Negative-QTOF	splash10-00di-0049000000-dcaf42c980626d7f79d2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 40V, Negative-QTOF	splash10-114l-1093000000-bde36cb4f1d86f3919a9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 10V, Positive-QTOF	splash10-00di-0009000000-c709cf6936a267877edb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 20V, Positive-QTOF	splash10-00dl-0069000000-78e27b89feac7be837aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 40V, Positive-QTOF	splash10-0005-0091000000-24f14a1f6662f113fe70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 10V, Negative-QTOF	splash10-00di-0009000000-991a74014b2b59c6013a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 20V, Negative-QTOF	splash10-00di-0029000000-2c033395678aa132bd19	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Neolitsine 40V, Negative-QTOF	splash10-0596-0098000000-4a28e4cb10ac087a239a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001007

KNApSAcK ID

Not Available

Chemspider ID

4944547

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440260

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (S)-Neolitsine (HMDB0033358)

MOL for HMDB0033358 ((S)-Neolitsine)

3D MOL for HMDB0033358 ((S)-Neolitsine)

3D SDF for HMDB0033358 ((S)-Neolitsine)

3D-SDF for HMDB0033358 ((S)-Neolitsine)

PDB for HMDB0033358 ((S)-Neolitsine)

3D PDB for HMDB0033358 ((S)-Neolitsine)

SMILES for HMDB0033358 ((S)-Neolitsine)

INCHI for HMDB0033358 ((S)-Neolitsine)

Structure for HMDB0033358 ((S)-Neolitsine)

3D Structure for HMDB0033358 ((S)-Neolitsine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra