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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:04 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033450

Secondary Accession Numbers

HMDB33450

Metabolite Identification

Common Name

Retrofractamide D

Description

Retrofractamide D 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 D.

Structure

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

HMDB0033450
     RDKit          3D
Retrofractamide D
 52 53  0  0  0  0  0  0  0  0999 V2000
    9.0410    1.8666   -1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6337    1.6445   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6727    1.1237    0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7722    1.0264   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504    0.7397   -1.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1068   -0.3302   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -1.0407   -0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7771   -0.4544   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.6131    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.7120    0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -1.6318    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3694   -1.9716    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.3310    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -1.2888    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5238   -0.6260    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518   -0.9408   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -0.2583   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0541    0.7548    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933    1.4084    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3203    1.0580   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0988    0.0415   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8678   -0.5883   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2468   -0.1175   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2741    0.6653   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6146    1.5296   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    0.9349   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5396    2.6433   -0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9637    2.0988   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1941    2.7303   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274    0.2095    0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6687    1.0743    1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    1.9460    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266    0.0862   -2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7206    1.7969   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    1.3444   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696   -1.5048    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197    0.3804   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975   -0.0911    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -2.2123    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865   -2.0647    3.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -3.1037    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -0.3197    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9339    2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -2.3826    0.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.9581   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    0.1996    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3970   -1.7729   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3107    1.1091    1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4878    2.2059    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6932   -1.4108   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7881    1.2816   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9556    0.0511   -0.5838 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 22 17  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
M  END

  Mrv0541 02241211022D          

 25 26  0  0  0  0            999 V2000
   -5.0824   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0824    0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685    1.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6559    0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6559   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678   -0.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3547    0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678    1.0810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9406   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0825   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3479   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0631   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089   -0.4113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937    0.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6394   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3547   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6394   -1.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102   -0.4127    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 25  1  0  0  0  0
 12 13  1  0  0  0  0
 12 24  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033450

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO3/c1-17(2)15-22-21(23)11-9-7-5-3-4-6-8-10-18-12-13-19-20(14-18)25-16-24-19/h5,7-14,17H,3-4,6,15-16H2,1-2H3,(H,22,23)/b7-5+,10-8+,11-9+

> <INCHI_KEY>
QVKVGYVXAAXMSX-HJHGIKLDSA-N

> <FORMULA>
C21H27NO3

> <MOLECULAR_WEIGHT>
341.444

> <EXACT_MASS>
341.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
40.18044963309575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,9E)-10-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)deca-2,4,9-trienamide

> <ALOGPS_LOGP>
5.10

> <JCHEM_LOGP>
4.8084936973333345

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.377879803618693

> <JCHEM_PKA_STRONGEST_BASIC>
2.2456184769564462

> <JCHEM_POLAR_SURFACE_AREA>
47.56

> <JCHEM_REFRACTIVITY>
103.7301

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,9E)-10-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)deca-2,4,9-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033450
     RDKit          3D
Retrofractamide D
 52 53  0  0  0  0  0  0  0  0999 V2000
    9.0410    1.8666   -1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6337    1.6445   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6727    1.1237    0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7722    1.0264   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504    0.7397   -1.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1068   -0.3302   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -1.0407   -0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7771   -0.4544   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.6131    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.7120    0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -1.6318    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3694   -1.9716    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.3310    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -1.2888    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5238   -0.6260    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518   -0.9408   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -0.2583   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0541    0.7548    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933    1.4084    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3203    1.0580   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0988    0.0415   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8678   -0.5883   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2468   -0.1175   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2741    0.6653   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6146    1.5296   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    0.9349   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5396    2.6433   -0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9637    2.0988   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1941    2.7303   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274    0.2095    0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6687    1.0743    1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    1.9460    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266    0.0862   -2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7206    1.7969   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    1.3444   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696   -1.5048    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197    0.3804   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975   -0.0911    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -2.2123    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865   -2.0647    3.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -3.1037    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -0.3197    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9339    2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -2.3826    0.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.9581   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    0.1996    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3970   -1.7729   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3107    1.1091    1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4878    2.2059    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6932   -1.4108   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7881    1.2816   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9556    0.0511   -0.5838 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 22 17  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  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      -9.487  -0.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.487   1.538   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.155   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.824   1.538   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.824  -0.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.155  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -10.953  -0.480   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -11.862   0.768   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -10.953   2.018   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.489  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.154  -0.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.154  -0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.181  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.516  -0.768   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.851  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.186  -0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.522  -0.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.857  -0.768   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       6.522   1.533   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.192  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.527  -0.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.862  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.527  -2.308   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.487  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.819  -0.770   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   25                                                       
CONECT   12   13   24                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12   25                                                       
CONECT   25   11   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0033450
HETATM    1  C1  UNL     1       9.041   1.867  -1.282  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.634   1.644  -0.743  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.673   1.124   0.634  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.772   1.026  -1.780  1.00  0.00           C  
HETATM    5  N1  UNL     1       5.450   0.740  -1.362  1.00  0.00           N  
HETATM    6  C5  UNL     1       5.107  -0.330  -0.425  1.00  0.00           C  
HETATM    7  O1  UNL     1       6.079  -1.041  -0.040  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.777  -0.454  -0.054  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.632  -0.613   0.313  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.296  -0.712   0.658  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.897  -1.632   1.566  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.369  -1.972   2.112  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.635  -1.331   1.821  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.182  -1.289   0.432  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.524  -0.626   0.430  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.552  -0.941  -0.310  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.836  -0.258  -0.258  1.00  0.00           C  
HETATM   18  C16 UNL     1      -6.054   0.755   0.644  1.00  0.00           C  
HETATM   19  C17 UNL     1      -7.293   1.408   0.697  1.00  0.00           C  
HETATM   20  C18 UNL     1      -8.320   1.058  -0.152  1.00  0.00           C  
HETATM   21  C19 UNL     1      -8.099   0.041  -1.055  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.868  -0.588  -1.084  1.00  0.00           C  
HETATM   23  O2  UNL     1      -9.247  -0.117  -1.765  1.00  0.00           O  
HETATM   24  C21 UNL     1     -10.274   0.665  -1.195  1.00  0.00           C  
HETATM   25  O3  UNL     1      -9.615   1.530  -0.312  1.00  0.00           O  
HETATM   26  H1  UNL     1       9.626   0.935  -1.118  1.00  0.00           H  
HETATM   27  H2  UNL     1       9.540   2.643  -0.682  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.964   2.099  -2.356  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.194   2.730  -0.645  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.227   0.210   0.792  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.669   1.074   1.152  1.00  0.00           H  
HETATM   32  H7  UNL     1       8.218   1.946   1.255  1.00  0.00           H  
HETATM   33  H8  UNL     1       7.227   0.086  -2.237  1.00  0.00           H  
HETATM   34  H9  UNL     1       6.721   1.797  -2.625  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.674   1.344  -1.735  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.070  -1.505   0.886  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.320   0.380  -0.669  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.498  -0.091   0.282  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.804  -2.212   1.933  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.286  -2.065   3.266  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.520  -3.104   1.868  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.772  -0.320   2.340  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.441  -1.934   2.394  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.432  -2.383   0.191  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.492  -0.958  -0.304  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.664   0.200   1.157  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.397  -1.773  -1.025  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.311   1.109   1.335  1.00  0.00           H  
HETATM   49  H24 UNL     1      -7.488   2.206   1.407  1.00  0.00           H  
HETATM   50  H25 UNL     1      -6.693  -1.411  -1.803  1.00  0.00           H  
HETATM   51  H26 UNL     1     -10.788   1.282  -1.967  1.00  0.00           H  
HETATM   52  H27 UNL     1     -10.956   0.051  -0.584  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5   33   34
CONECT    5    6   35
CONECT    6    7    7    8
CONECT    8    9    9   36
CONECT    9   10   37
CONECT   10   11   11   38
CONECT   11   12   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   18   22
CONECT   18   19   48
CONECT   19   20   20   49
CONECT   20   21   25
CONECT   21   22   22   23
CONECT   22   50
CONECT   23   24
CONECT   24   25   51   52
END

HMDB0033450
     RDKit          3D
Retrofractamide D
 52 53  0  0  0  0  0  0  0  0999 V2000
    9.0410    1.8666   -1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6337    1.6445   -0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6727    1.1237    0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7722    1.0264   -1.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4504    0.7397   -1.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1068   -0.3302   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -1.0407   -0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7771   -0.4544   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.6131    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2957   -0.7120    0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968   -1.6318    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3694   -1.9716    2.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.3310    1.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819   -1.2888    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5238   -0.6260    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518   -0.9408   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -0.2583   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0541    0.7548    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933    1.4084    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3203    1.0580   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0988    0.0415   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8678   -0.5883   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2468   -0.1175   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2741    0.6653   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6146    1.5296   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6262    0.9349   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5396    2.6433   -0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9637    2.0988   -2.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1941    2.7303   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2274    0.2095    0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6687    1.0743    1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    1.9460    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266    0.0862   -2.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7206    1.7969   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6741    1.3444   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0696   -1.5048    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197    0.3804   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4975   -0.0911    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8035   -2.2123    1.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865   -2.0647    3.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -3.1037    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -0.3197    2.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9339    2.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -2.3826    0.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921   -0.9581   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6641    0.1996    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3970   -1.7729   -1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3107    1.1091    1.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4878    2.2059    1.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6932   -1.4108   -1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7881    1.2816   -1.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9556    0.0511   -0.5838 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 22 17  1  0
 25 20  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 19 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E,9E)-10-(2H-1,3-Benzodioxol-5-yl)-N-(2-methylpropyl)deca-2,4,9-trienimidate	HMDB

Chemical Formula

C₂₁H₂₇NO₃

Average Molecular Weight

341.444

Monoisotopic Molecular Weight

341.199093735

IUPAC Name

(2E,4E,9E)-10-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)deca-2,4,9-trienamide

Traditional Name

(2E,4E,9E)-10-(2H-1,3-benzodioxol-5-yl)-N-(2-methylpropyl)deca-2,4,9-trienamide

CAS Registry Number

96386-34-4

SMILES

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

InChI Identifier

InChI=1S/C21H27NO3/c1-17(2)15-22-21(23)11-9-7-5-3-4-6-8-10-18-12-13-19-20(14-18)25-16-24-19/h5,7-14,17H,3-4,6,15-16H2,1-2H3,(H,22,23)/b7-5+,10-8+,11-9+

InChI Key

QVKVGYVXAAXMSX-HJHGIKLDSA-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: HMDB0033450)

Exogenous

Food

Food (HMDB: HMDB0033450)

Exogenous (HMDB: HMDB0033450)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0033450)

Role

Biological role

Energy source (HMDB: HMDB0033450)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033450)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 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	0.00098 g/L	ALOGPS
logP	5.1	ALOGPS
logP	4.81	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.38	ChemAxon
pKa (Strongest Basic)	2.25	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	103.73 m³·mol⁻¹	ChemAxon
Polarizability	40.18 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]+	185.517	30932474
DeepCCS	[M-H]-	183.104	30932474
DeepCCS	[M-2H]-	217.37	30932474
DeepCCS	[M+Na]+	193.423	30932474
AllCCS	[M+H]+	186.9	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.4	32859911
AllCCS	[M-H]-	188.5	32859911
AllCCS	[M+Na-2H]-	189.1	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retrofractamide D	CC(C)CNC(=O)\C=C\C=C\CCC\C=C\C1=CC2=C(OCO2)C=C1	4535.7	Standard polar	33892256
Retrofractamide D	CC(C)CNC(=O)\C=C\C=C\CCC\C=C\C1=CC2=C(OCO2)C=C1	2864.1	Standard non polar	33892256
Retrofractamide D	CC(C)CNC(=O)\C=C\C=C\CCC\C=C\C1=CC2=C(OCO2)C=C1	3180.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retrofractamide D,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/C=C/CCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C	3017.6	Semi standard non polar	33892256
Retrofractamide D,1TMS,isomer #1	CC(C)CN(C(=O)/C=C/C=C/CCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C	2952.6	Standard non polar	33892256
Retrofractamide D,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/C=C/CCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	3209.4	Semi standard non polar	33892256
Retrofractamide D,1TBDMS,isomer #1	CC(C)CN(C(=O)/C=C/C=C/CCC/C=C/C1=CC=C2OCOC2=C1)[Si](C)(C)C(C)(C)C	3159.1	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 D GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-2961000000-49593b8691928fe78604	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retrofractamide D 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 D 10V, Positive-QTOF	splash10-00di-9013000000-9455bcfef8c2efbaddec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 20V, Positive-QTOF	splash10-00di-9010000000-a83faef680366958967b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 40V, Positive-QTOF	splash10-0ab9-9000000000-f31286d7f95094d55d2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 10V, Negative-QTOF	splash10-0006-1039000000-0b4a6896c209428afd58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 20V, Negative-QTOF	splash10-006x-4195000000-56d8b9434096b8a929f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 40V, Negative-QTOF	splash10-006x-8190000000-01160d3b2137528b6107	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 10V, Positive-QTOF	splash10-0006-0019000000-2642ac3ca3164bf432f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 20V, Positive-QTOF	splash10-0axu-6193000000-f69ab342f5784873fb5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 40V, Positive-QTOF	splash10-0005-5930000000-bcdf5b7eaa55849b252a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 10V, Negative-QTOF	splash10-0006-0009000000-d9e306a9551481b61192	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 20V, Negative-QTOF	splash10-0006-1039000000-6dbab1a0333a03582c85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retrofractamide D 40V, Negative-QTOF	splash10-000g-9772000000-595bc4726acac943168d	2021-09-22	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

FDB011488

KNApSAcK ID

C00057706

Chemspider ID

30777001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751424

PDB ID

Not Available

ChEBI ID

174599

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 D (HMDB0033450)

MOL for HMDB0033450 (Retrofractamide D)

3D MOL for HMDB0033450 (Retrofractamide D)

3D SDF for HMDB0033450 (Retrofractamide D)

3D-SDF for HMDB0033450 (Retrofractamide D)

PDB for HMDB0033450 (Retrofractamide D)

3D PDB for HMDB0033450 (Retrofractamide D)

SMILES for HMDB0033450 (Retrofractamide D)

INCHI for HMDB0033450 (Retrofractamide D)

Structure for HMDB0033450 (Retrofractamide D)

3D Structure for HMDB0033450 (Retrofractamide D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra