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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:57 UTC

Update Date

2022-03-07 02:53:12 UTC

HMDB ID

HMDB0031976

Secondary Accession Numbers

HMDB31976

Metabolite Identification

Common Name

Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate

Description

Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms. Based on a literature review a significant number of articles have been published on Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate.

Structure

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

HMDB0031976
     RDKit          3D
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate
 47 46  0  0  0  0  0  0  0  0999 V2000
    8.6393   -1.5678    2.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0074   -0.7849    1.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6033   -0.7097    1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9440   -1.4032    2.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1134    0.1386    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.3236    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.2409   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550    1.9429   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    1.4121   -1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775    0.7469   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    1.0132   -0.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221    0.3899   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865    1.2953   -1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.1311    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -0.7447    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -0.4511    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -1.0091    0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9032   -0.6111    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7982    0.3562   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1615   -1.1267    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3499   -0.8185    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5823   -1.3982    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6761   -1.0402    0.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -2.0305    3.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1464   -2.4010    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834   -0.9879    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500    0.6971    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271   -0.2148    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2866    2.5516   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    1.0803   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402    2.4159   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    2.1159   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.0541    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.7094   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.4465   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    1.8174   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    1.8468   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2428   -0.8239    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -1.4700    1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    0.2545   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.7075    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0935   -0.1120   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    1.3637   -0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7694    0.3850   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1427   -1.8394    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.1441   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5356   -2.0704    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
M  END

  Mrv0541 05061306162D          

 23 22  0  0  0  0            999 V2000
    3.3000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17  1  1  0  0  0  0
 17  9  2  0  0  0  0
 17 11  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  2  0  0  0  0
 18 13  1  0  0  0  0
 19  3  1  0  0  0  0
 19 12  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  2  0  0  0  0
 22 20  2  0  0  0  0
 23  4  1  0  0  0  0
 23 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031976

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O3/c1-17(9-5-6-10-18(2)13-8-16-21)11-7-12-19(3)14-15-20(22)23-4/h5-16H,1-4H3/b6-5+,11-7+,13-8+,15-14+,17-9+,18-10+,19-12-

> <INCHI_KEY>
NXZZZYUALZNGOO-OKMAZBOSSA-N

> <FORMULA>
C20H24O3

> <MOLECULAR_WEIGHT>
312.4028

> <EXACT_MASS>
312.172544634

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.49241848418512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

> <ALOGPS_LOGP>
5.09

> <JCHEM_LOGP>
4.073074660666666

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.30181485109397

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
103.2083

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031976
     RDKit          3D
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate
 47 46  0  0  0  0  0  0  0  0999 V2000
    8.6393   -1.5678    2.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0074   -0.7849    1.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6033   -0.7097    1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9440   -1.4032    2.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1134    0.1386    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.3236    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.2409   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550    1.9429   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    1.4121   -1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775    0.7469   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    1.0132   -0.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221    0.3899   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865    1.2953   -1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.1311    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -0.7447    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -0.4511    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -1.0091    0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9032   -0.6111    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7982    0.3562   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1615   -1.1267    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3499   -0.8185    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5823   -1.3982    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6761   -1.0402    0.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -2.0305    3.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1464   -2.4010    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834   -0.9879    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500    0.6971    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271   -0.2148    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2866    2.5516   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    1.0803   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402    2.4159   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    2.1159   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.0541    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.7094   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.4465   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    1.8174   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    1.8468   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2428   -0.8239    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -1.4700    1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    0.2545   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.7075    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0935   -0.1120   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    1.3637   -0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7694    0.3850   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1427   -1.8394    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.1441   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5356   -2.0704    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  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       6.160  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850  -6.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850 -12.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620 -10.669   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620 -13.337   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.850  -9.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.160 -13.337   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   23                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7   11   12                                                       
CONECT    8   13   16                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11    7   17                                                       
CONECT   12    7   19                                                       
CONECT   13    8   18                                                       
CONECT   14   15   19                                                       
CONECT   15   14   20                                                       
CONECT   16    8   21                                                       
CONECT   17    1    9   11                                                  
CONECT   18    2   10   13                                                  
CONECT   19    3   12   14                                                  
CONECT   20   15   22   23                                                  
CONECT   21   16                                                            
CONECT   22   20                                                            
CONECT   23    4   20                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0031976
HETATM    1  C1  UNL     1       8.639  -1.568   2.964  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.007  -0.785   1.993  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.603  -0.710   1.813  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.944  -1.403   2.606  1.00  0.00           O  
HETATM    5  C3  UNL     1       6.113   0.139   0.760  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.859   0.324   0.412  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.522   1.241  -0.702  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.655   1.943  -1.421  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.296   1.412  -1.053  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.178   0.747  -0.422  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.912   1.013  -0.890  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.222   0.390  -0.313  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.387   1.295  -1.413  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.170  -0.131   0.169  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.279  -0.745   0.738  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.526  -0.451   0.266  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.757  -1.009   0.766  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.903  -0.611   0.155  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.798   0.356  -0.978  1.00  0.00           C  
HETATM   20  C18 UNL     1      -7.161  -1.127   0.639  1.00  0.00           C  
HETATM   21  C19 UNL     1      -8.350  -0.819   0.138  1.00  0.00           C  
HETATM   22  C20 UNL     1      -9.582  -1.398   0.706  1.00  0.00           C  
HETATM   23  O3  UNL     1     -10.676  -1.040   0.153  1.00  0.00           O  
HETATM   24  H1  UNL     1       8.001  -2.031   3.707  1.00  0.00           H  
HETATM   25  H2  UNL     1       9.146  -2.401   2.378  1.00  0.00           H  
HETATM   26  H3  UNL     1       9.483  -0.988   3.406  1.00  0.00           H  
HETATM   27  H4  UNL     1       6.850   0.697   0.171  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.127  -0.215   0.976  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.287   2.552  -2.249  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.225   1.080  -1.887  1.00  0.00           H  
HETATM   31  H8  UNL     1       6.340   2.416  -0.732  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.144   2.116  -1.896  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.201   0.054   0.384  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.908   1.709  -1.699  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.714   0.446  -1.932  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.834   1.817  -0.619  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.624   1.847  -1.893  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.243  -0.824   1.006  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.334  -1.470   1.551  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.547   0.254  -0.536  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.875  -1.708   1.569  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.093  -0.112  -1.723  1.00  0.00           H  
HETATM   43  H20 UNL     1      -5.518   1.364  -0.681  1.00  0.00           H  
HETATM   44  H21 UNL     1      -6.769   0.385  -1.500  1.00  0.00           H  
HETATM   45  H22 UNL     1      -7.143  -1.839   1.490  1.00  0.00           H  
HETATM   46  H23 UNL     1      -8.398  -0.144  -0.681  1.00  0.00           H  
HETATM   47  H24 UNL     1      -9.536  -2.070   1.530  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   27
CONECT    6    7   28
CONECT    7    8    9    9
CONECT    8   29   30   31
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   14   14
CONECT   13   35   36   37
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   17   40
CONECT   17   18   18   41
CONECT   18   19   20
CONECT   19   42   43   44
CONECT   20   21   21   45
CONECT   21   22   46
CONECT   22   23   23   47
END

HMDB0031976
     RDKit          3D
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate
 47 46  0  0  0  0  0  0  0  0999 V2000
    8.6393   -1.5678    2.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0074   -0.7849    1.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6033   -0.7097    1.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9440   -1.4032    2.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1134    0.1386    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8586    0.3236    0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    1.2409   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550    1.9429   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958    1.4121   -1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1775    0.7469   -0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120    1.0132   -0.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2221    0.3899   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865    1.2953   -1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1702   -0.1311    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -0.7447    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -0.4511    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -1.0091    0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9032   -0.6111    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7982    0.3562   -0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1615   -1.1267    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3499   -0.8185    0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5823   -1.3982    0.7064 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6761   -1.0402    0.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011   -2.0305    3.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1464   -2.4010    2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4834   -0.9879    3.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500    0.6971    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271   -0.2148    0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2866    2.5516   -2.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    1.0803   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402    2.4159   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    2.1159   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.0541    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078    1.7094   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.4465   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341    1.8174   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    1.8468   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2428   -0.8239    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -1.4700    1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    0.2545   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.7075    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0935   -0.1120   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5184    1.3637   -0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7694    0.3850   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1427   -1.8394    1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3981   -0.1441   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5356   -2.0704    1.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoic acid	Generator
apo-10'-Bixinal	HMDB
Methyl (4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoic acid	Generator

Chemical Formula

C₂₀H₂₄O₃

Average Molecular Weight

312.4028

Monoisotopic Molecular Weight

312.172544634

IUPAC Name

methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

Traditional Name

methyl (2E,4Z,6E,8E,10E,12E,14E)-4,8,13-trimethyl-16-oxohexadeca-2,4,6,8,10,12,14-heptaenoate

CAS Registry Number

201996-43-2

SMILES

COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O

InChI Identifier

InChI=1S/C20H24O3/c1-17(9-5-6-10-18(2)13-8-16-21)11-7-12-19(3)14-15-20(22)23-4/h5-16H,1-4H3/b6-5+,11-7+,13-8+,15-14+,17-9+,18-10+,19-12-

InChI Key

NXZZZYUALZNGOO-OKMAZBOSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty aldehydes

Direct Parent

Fatty aldehydes

Alternative Parents

Substituents

Fatty aldehyde
Acyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Alpha,beta-unsaturated aldehyde
Enal
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Organic oxygen 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

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0031976)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031976)

Source

Endogenous

Endogenous (HMDB: HMDB0031976)

Animal

Animal (HMDB: HMDB0031976)

Exogenous

Food

Food (HMDB: HMDB0031976)

Exogenous (HMDB: HMDB0031976)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031976)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031976)

Lipid metabolism pathway (HMDB: HMDB0031976)

Cellular process

Cell signaling (HMDB: HMDB0031976)

Biochemical process

Lipid transport (HMDB: HMDB0031976)

Role

Biological role

Energy source (HMDB: HMDB0031976)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031976)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.0052 g/L	ALOGPS
logP	5.09	ALOGPS
logP	4.07	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	103.21 m³·mol⁻¹	ChemAxon
Polarizability	37.49 Å³	ChemAxon
Number of Rings	0	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]+	186.661	31661259
DarkChem	[M-H]-	186.355	31661259
DeepCCS	[M+H]+	188.348	30932474
DeepCCS	[M-H]-	185.99	30932474
DeepCCS	[M-2H]-	219.901	30932474
DeepCCS	[M+Na]+	195.129	30932474
AllCCS	[M+H]+	183.1	32859911
AllCCS	[M+H-H2O]+	179.9	32859911
AllCCS	[M+NH4]+	186.1	32859911
AllCCS	[M+Na]+	186.9	32859911
AllCCS	[M-H]-	175.3	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate	COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O	4152.7	Standard polar	33892256
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate	COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O	2658.2	Standard non polar	33892256
Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate	COC(=O)\C=C\C(\C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=O	2840.7	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 - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7k-0290000000-5a2d56d89d239178d17d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 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 - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 10V, Positive-QTOF	splash10-01q9-1292000000-87980c08c19841549c7b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 20V, Positive-QTOF	splash10-003i-3950000000-ec6768b5a7ae9c0c2881	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 40V, Positive-QTOF	splash10-0560-7940000000-2a18b3513ba1768956c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 10V, Negative-QTOF	splash10-03di-0059000000-dfbd27540ad6d21bdb3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 20V, Negative-QTOF	splash10-03fr-2094000000-17b3f38d0d978f405f1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 40V, Negative-QTOF	splash10-01ox-8390000000-f76b977927b45da77f2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 10V, Negative-QTOF	splash10-014i-0192000000-1bb0ed2f05b26fbc2021	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 20V, Negative-QTOF	splash10-076r-5393000000-a62e5eea7e76a2828fe1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 40V, Negative-QTOF	splash10-00fs-1950000000-f11ef8d4400631f1ad18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 10V, Positive-QTOF	splash10-01q9-0190000000-1e84a115991596568a4c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 20V, Positive-QTOF	splash10-0f6y-3790000000-67d658f2338a8b49c560	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate 40V, Positive-QTOF	splash10-052f-4920000000-88192307fe5e2d814bf1	2021-09-25	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

FDB008669

KNApSAcK ID

C00023151

Chemspider ID

30776928

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751234

PDB ID

Not Available

ChEBI ID

169747

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate (HMDB0031976)

MOL for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

3D MOL for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

3D SDF for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

3D-SDF for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

PDB for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

3D PDB for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

SMILES for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

INCHI for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

Structure for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

3D Structure for HMDB0031976 (Methyl (9Z)-10'-oxo-6,10'-diapo-6-carotenoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra