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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:10:58 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033448

Secondary Accession Numbers

HMDB33448

Metabolite Identification

Common Name

Retrofractamide C

Description

Retrofractamide C belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Based on a literature review very few articles have been published on Retrofractamide C.

Structure

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

HMDB0033448
     RDKit          3D
Retrofractamide C
 51 52  0  0  0  0  0  0  0  0999 V2000
   -7.9444    0.3715   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5865   -0.1735   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549   -0.9579    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    1.0119   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.9014    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800    0.4653    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085    0.1343    2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707    0.3635    1.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6635    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.5427    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -0.4387    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.0063   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.9522   -1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -1.0203   -1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.2002   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571   -0.3093   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.2959   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064   -1.3511   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842   -0.4316    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6951    0.5668    0.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659    0.6115    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    1.3327    1.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8944    1.0545    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -0.2603    0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.4780   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7565    1.1654   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4338    0.8076   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2642   -0.8713   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8843   -1.5707    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2040   -1.7131    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3141   -0.3370    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289    1.7518    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7478    1.5384   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336    1.1827   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    0.0172    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441    1.0181   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.2011    2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674    1.5418    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305   -1.3647    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.8334    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    0.1020   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    1.0096   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8343   -1.9782   -1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -0.6378   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -1.8424   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    0.6467   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -2.0486   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -2.1365   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.3795    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5508    1.0591    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1928    1.7556    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 21 16  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
M  END

  Mrv0541 02241207532D          

 24 25  0  0  0  0            999 V2000
   -4.7258    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7258   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5113    0.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9981   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5113   -1.0824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5843    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1539    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4220    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8525    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1373    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9981    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2829   -0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033448

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CNC(=O)\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h7-13,16H,3-6,14-15H2,1-2H3,(H,21,22)/b9-7+,10-8+

> <INCHI_KEY>
PAXQNYHJDFKFEU-FIFLTTCUSA-N

> <FORMULA>
C20H27NO3

> <MOLECULAR_WEIGHT>
329.4333

> <EXACT_MASS>
329.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.59915487042838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
4.725846689

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.390155973825905

> <JCHEM_PKA_STRONGEST_BASIC>
2.347235460071277

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
98.01249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033448
     RDKit          3D
Retrofractamide C
 51 52  0  0  0  0  0  0  0  0999 V2000
   -7.9444    0.3715   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5865   -0.1735   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549   -0.9579    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    1.0119   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.9014    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800    0.4653    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085    0.1343    2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707    0.3635    1.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6635    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.5427    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -0.4387    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.0063   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.9522   -1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -1.0203   -1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.2002   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571   -0.3093   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.2959   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064   -1.3511   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842   -0.4316    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6951    0.5668    0.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659    0.6115    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    1.3327    1.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8944    1.0545    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -0.2603    0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.4780   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7565    1.1654   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4338    0.8076   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2642   -0.8713   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8843   -1.5707    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2040   -1.7131    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3141   -0.3370    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289    1.7518    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7478    1.5384   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336    1.1827   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    0.0172    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441    1.0181   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.2011    2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674    1.5418    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305   -1.3647    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.8334    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    0.1020   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    1.0096   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8343   -1.9782   -1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -0.6378   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -1.8424   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    0.6467   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -2.0486   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -2.1365   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.3795    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5508    1.0591    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1928    1.7556    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 21 16  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.821   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.821  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.489  -2.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.159  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.159   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.489   0.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -10.288   0.477   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -11.196  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -10.288  -2.020   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.824   0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.489   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.154   0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.819   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.516   0.768   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.851   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.186   0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.521   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.856   0.768   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.191   0.000   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.856   2.311   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.526   0.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.861   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.196   0.768   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.861  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8                                                       
CONECT   10    5   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0033448
HETATM    1  C1  UNL     1      -7.944   0.372  -1.073  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.587  -0.173  -0.534  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.955  -0.958   0.677  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.724   1.012  -0.390  1.00  0.00           C  
HETATM    5  N1  UNL     1      -4.401   0.901   0.056  1.00  0.00           N  
HETATM    6  C5  UNL     1      -3.980   0.465   1.314  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.809   0.134   2.188  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.571   0.363   1.700  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.555   0.664   0.926  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.140   0.543   1.367  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.559  -0.439   0.454  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.547   0.006  -0.991  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.279  -0.952  -1.861  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.709  -1.020  -1.524  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.331  -0.200  -0.739  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.757  -0.309  -0.429  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.541  -1.296  -0.951  1.00  0.00           C  
HETATM   18  C16 UNL     1       6.906  -1.351  -0.617  1.00  0.00           C  
HETATM   19  C17 UNL     1       7.484  -0.432   0.229  1.00  0.00           C  
HETATM   20  C18 UNL     1       6.695   0.567   0.759  1.00  0.00           C  
HETATM   21  C19 UNL     1       5.366   0.611   0.427  1.00  0.00           C  
HETATM   22  O2  UNL     1       7.540   1.333   1.564  1.00  0.00           O  
HETATM   23  C20 UNL     1       8.894   1.055   1.269  1.00  0.00           C  
HETATM   24  O3  UNL     1       8.775  -0.260   0.712  1.00  0.00           O  
HETATM   25  H1  UNL     1      -8.520  -0.478  -1.454  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.756   1.165  -1.797  1.00  0.00           H  
HETATM   27  H3  UNL     1      -8.434   0.808  -0.173  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.264  -0.871  -1.341  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.884  -1.571   0.380  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.204  -1.713   0.921  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.314  -0.337   1.515  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.329   1.752   0.256  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.748   1.538  -1.402  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.634   1.183  -0.649  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.318   0.017   2.694  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.744   1.018  -0.072  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.055   0.201   2.411  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.367   1.542   1.332  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.131  -1.365   0.455  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.498  -0.833   0.826  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.511   0.102  -1.360  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.978   1.010  -1.085  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.834  -1.978  -1.812  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.188  -0.638  -2.926  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.290  -1.842  -1.983  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.765   0.647  -0.296  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.179  -2.049  -1.614  1.00  0.00           H  
HETATM   48  H24 UNL     1       7.536  -2.137  -1.032  1.00  0.00           H  
HETATM   49  H25 UNL     1       4.748   1.380   0.832  1.00  0.00           H  
HETATM   50  H26 UNL     1       9.551   1.059   2.138  1.00  0.00           H  
HETATM   51  H27 UNL     1       9.193   1.756   0.462  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29   30   31
CONECT    4    5   32   33
CONECT    5    6   34
CONECT    6    7    7    8
CONECT    8    9    9   35
CONECT    9   10   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   15   45
CONECT   15   16   46
CONECT   16   17   17   21
CONECT   17   18   47
CONECT   18   19   19   48
CONECT   19   20   24
CONECT   20   21   21   22
CONECT   21   49
CONECT   22   23
CONECT   23   24   50   51
END

HMDB0033448
     RDKit          3D
Retrofractamide C
 51 52  0  0  0  0  0  0  0  0999 V2000
   -7.9444    0.3715   -1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5865   -0.1735   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549   -0.9579    0.6771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    1.0119   -0.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.9014    0.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9800    0.4653    1.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085    0.1343    2.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707    0.3635    1.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5554    0.6635    0.9265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1404    0.5427    1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -0.4387    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.0063   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -0.9522   -1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -1.0203   -1.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3307   -0.2002   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571   -0.3093   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.2959   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9064   -1.3511   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4842   -0.4316    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6951    0.5668    0.7592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659    0.6115    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5400    1.3327    1.5643 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8944    1.0545    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -0.2603    0.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201   -0.4780   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7565    1.1654   -1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4338    0.8076   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2642   -0.8713   -1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8843   -1.5707    0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2040   -1.7131    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3141   -0.3370    1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3289    1.7518    0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7478    1.5384   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336    1.1827   -0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    0.0172    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441    1.0181   -0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546    0.2011    2.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3674    1.5418    1.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305   -1.3647    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -0.8334    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5113    0.1020   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    1.0096   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8343   -1.9782   -1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -0.6378   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -1.8424   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    0.6467   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1793   -2.0486   -1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5355   -2.1365   -1.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7475    1.3795    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5508    1.0591    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1928    1.7556    0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 21 16  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,8E)-9-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienimidate	HMDB

Chemical Formula

C₂₀H₂₇NO₃

Average Molecular Weight

329.4333

Monoisotopic Molecular Weight

329.199093735

IUPAC Name

(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide

Traditional Name

(2E,8E)-9-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,8-dienamide

CAS Registry Number

96386-33-3

SMILES

CC(C)CNC(=O)\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C20H27NO3/c1-16(2)14-21-20(22)10-8-6-4-3-5-7-9-17-11-12-18-19(13-17)24-15-23-18/h7-13,16H,3-6,14-15H2,1-2H3,(H,21,22)/b9-7+,10-8+

InChI Key

PAXQNYHJDFKFEU-FIFLTTCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
N-acyl-amine
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Acetal
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0033448)

Exogenous

Food

Food (HMDB: HMDB0033448)

Exogenous (HMDB: HMDB0033448)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0033448)

Role

Biological role

Energy source (HMDB: HMDB0033448)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033448)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	120 °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	0.0012 g/L	ALOGPS
logP	4.87	ALOGPS
logP	4.73	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	16.39	ChemAxon
pKa (Strongest Basic)	2.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.56 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	98.01 m³·mol⁻¹	ChemAxon
Polarizability	39.6 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	184.375	30932474
DeepCCS	[M-H]-	181.831	30932474
DeepCCS	[M-2H]-	215.724	30932474
DeepCCS	[M+Na]+	191.447	30932474
AllCCS	[M+H]+	182.9	32859911
AllCCS	[M+H-H2O]+	179.9	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	185.9	32859911
AllCCS	[M+Na-2H]-	186.6	32859911
AllCCS	[M+HCOO]-	187.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retrofractamide C	CC(C)CNC(=O)\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1	4263.6	Standard polar	33892256
Retrofractamide C	CC(C)CNC(=O)\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1	2742.7	Standard non polar	33892256
Retrofractamide C	CC(C)CNC(=O)\C=C\CCCC\C=C\C1=CC2=C(OCO2)C=C1	2975.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retrofractamide C,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C	2805.8	Semi standard non polar	33892256
Retrofractamide C,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C	2809.8	Standard non polar	33892256
Retrofractamide C,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	3003.6	Semi standard non polar	33892256
Retrofractamide C,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/CCCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	3025.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Retrofractamide C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-1950000000-27b6236c9d4677178314	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retrofractamide C 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 - Retrofractamide C 10V, Positive-QTOF	splash10-00di-9003000000-fdf0cf07e4c3201a557c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 20V, Positive-QTOF	splash10-00di-9010000000-22d1816737e5cafff209	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 40V, Positive-QTOF	splash10-0ab9-9000000000-03898f6691c51472329f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 10V, Negative-QTOF	splash10-004i-1039000000-ffb10ee211885a6fc82e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 20V, Negative-QTOF	splash10-00b9-4195000000-2725d4b2c720782ebfa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 40V, Negative-QTOF	splash10-00fu-8190000000-85f1058524980c28cb3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 10V, Positive-QTOF	splash10-001i-0019000000-57fd04c551b22f632592	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 20V, Positive-QTOF	splash10-0a59-5294000000-0d156996d745cd09da28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 40V, Positive-QTOF	splash10-0c03-8940000000-c89767fcc9a817179803	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 10V, Negative-QTOF	splash10-004i-0009000000-6cc27dc93d39f13756ea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 20V, Negative-QTOF	splash10-004i-2029000000-0dd346aed07a6aff6d11	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide C 40V, Negative-QTOF	splash10-01ow-6922000000-942f691751f98a543101	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB011486

KNApSAcK ID

C00057705

Chemspider ID

23321408

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25255091

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 Retrofractamide C (HMDB0033448)

MOL for HMDB0033448 (Retrofractamide C)

3D MOL for HMDB0033448 (Retrofractamide C)

3D SDF for HMDB0033448 (Retrofractamide C)

3D-SDF for HMDB0033448 (Retrofractamide C)

PDB for HMDB0033448 (Retrofractamide C)

3D PDB for HMDB0033448 (Retrofractamide C)

SMILES for HMDB0033448 (Retrofractamide C)

INCHI for HMDB0033448 (Retrofractamide C)

Structure for HMDB0033448 (Retrofractamide C)

3D Structure for HMDB0033448 (Retrofractamide C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra