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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18) Show 18 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001358

Secondary Accession Numbers

HMDB01358

Metabolite Identification

Common Name

Retinal

Description

Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration.

Structure

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

HMDB0001358
     RDKit          3D
Retinal
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.2811    0.9418    1.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824    1.5605    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    1.3741   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.5703    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.0616    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.8292    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -1.4556    2.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -1.0675    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341   -1.8707    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -2.1432   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -2.9292    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.5394    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0105   -3.1728   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1495   -3.9702   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0784   -4.1604   -0.9537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    2.0468   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808    1.3161   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    2.1264   -2.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767    3.5008   -1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    3.6614   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5595    2.4024    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207    1.1771    2.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138    1.3807    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1810   -0.1540    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    0.5907   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120   -0.2014    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023   -1.1405    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -1.1943    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.5679    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.6525   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403   -2.2648    1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -1.7494   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -4.6654    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446   -3.1012    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -3.3704    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -2.7592   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2209   -4.3929    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.3557   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    1.0858   -3.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.9385   -2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    1.1755   -2.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.9165   -3.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    2.3921   -1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    3.9701   -0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393    3.9657   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0956    3.9757   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    4.4913    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3154    1.7771   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095    2.7204    1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
M  END


  Mrv1652303192021402D          

 21 21  0  0  0  0            999 V2000
 9999.479210002.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.193910001.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.908410002.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.622910001.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.337210002.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.052710001.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.765910002.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.481310001.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.198710002.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.912010001.8005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.765910003.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.908410003.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.047310000.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.577510001.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.052110003.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.050710002.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.336110001.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.336110000.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.050710000.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.765410000.9754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.765410001.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001358

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

> <INCHI_KEY>
NCYCYZXNIZJOKI-OVSJKPMPSA-N

> <FORMULA>
C20H28O

> <MOLECULAR_WEIGHT>
284.4357

> <EXACT_MASS>
284.214015518

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.69258909408052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
4.855751458666667

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.061304726121949

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
96.8654

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retinaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001358
     RDKit          3D
Retinal
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.2811    0.9418    1.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824    1.5605    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    1.3741   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.5703    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.0616    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.8292    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -1.4556    2.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -1.0675    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341   -1.8707    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -2.1432   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -2.9292    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.5394    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0105   -3.1728   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1495   -3.9702   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0784   -4.1604   -0.9537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    2.0468   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808    1.3161   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    2.1264   -2.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767    3.5008   -1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    3.6614   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5595    2.4024    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207    1.1771    2.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138    1.3807    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1810   -0.1540    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    0.5907   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120   -0.2014    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023   -1.1405    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -1.1943    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.5679    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.6525   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403   -2.2648    1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -1.7494   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -4.6654    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446   -3.1012    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -3.3704    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -2.7592   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2209   -4.3929    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.3557   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    1.0858   -3.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.9385   -2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    1.1755   -2.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.9165   -3.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    2.3921   -1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    3.9701   -0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393    3.9657   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0956    3.9757   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    4.4913    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3154    1.7771   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095    2.7204    1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.6958670.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.0298670.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.3628670.797   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.6968670.028   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.0298670.797   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.3658670.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8673.6968670.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8675.0328670.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8676.3718670.797   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8677.7028670.028   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8673.6968672.337   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.3628672.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.8888667.040   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.8788668.756   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.0318672.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.0288670.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8661.6948670.028   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.6948668.487   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.0288667.718   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.3628668.487   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8664.3628670.028   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    3                                                            
CONECT   13   20                                                            
CONECT   14   20                                                            
CONECT   15   16                                                            
CONECT   16   17   21   15                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   13   14                                             
CONECT   21   16   20    1                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0001358
HETATM    1  C1  UNL     1      -3.281   0.942   1.975  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.382   1.561   0.661  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.374   1.374  -0.231  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.256   0.570   0.222  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.377  -0.062   0.577  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.690  -0.829   1.010  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.868  -1.456   2.328  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.716  -1.068   0.143  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.834  -1.871   0.607  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.859  -2.143  -0.183  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.994  -2.929   0.241  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.167  -3.539   1.595  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.010  -3.173  -0.591  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.149  -3.970  -0.144  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.078  -4.160  -0.954  1.00  0.00           O  
HETATM   16  C15 UNL     1      -2.584   2.047  -1.502  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.681   1.316  -2.266  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.354   2.126  -2.387  1.00  0.00           C  
HETATM   19  C18 UNL     1      -2.977   3.501  -1.260  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.197   3.661  -0.415  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.559   2.402   0.331  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.221   1.177   2.578  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.414   1.381   2.509  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.181  -0.154   1.918  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.675   0.591  -1.096  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.012  -0.201   1.842  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.802  -1.140   2.823  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.059  -1.194   3.043  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.781  -2.568   2.205  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.640  -0.653  -0.837  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.840  -2.265   1.601  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.798  -1.749  -1.180  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.256  -4.665   1.537  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.045  -3.101   2.116  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.283  -3.370   2.245  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.924  -2.759  -1.573  1.00  0.00           H  
HETATM   37  H16 UNL     1       7.221  -4.393   0.837  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.846   0.356  -1.772  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.269   1.086  -3.289  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.591   1.939  -2.381  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.196   1.176  -2.926  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.500   2.916  -3.178  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.447   2.392  -1.819  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.074   3.970  -0.775  1.00  0.00           H  
HETATM   45  H24 UNL     1      -3.139   3.966  -2.236  1.00  0.00           H  
HETATM   46  H25 UNL     1      -5.096   3.976  -1.018  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.007   4.491   0.299  1.00  0.00           H  
HETATM   48  H27 UNL     1      -5.315   1.777  -0.168  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.009   2.720   1.293  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   16
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    8    8
CONECT    7   27   28   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   13   13
CONECT   12   33   34   35
CONECT   13   14   36
CONECT   14   15   15   37
CONECT   16   17   18   19
CONECT   17   38   39   40
CONECT   18   41   42   43
CONECT   19   20   44   45
CONECT   20   21   46   47
CONECT   21   48   49
END

HMDB0001358
     RDKit          3D
Retinal
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.2811    0.9418    1.9748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3824    1.5605    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3738    1.3741   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.5703    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -0.0616    0.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.8292    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -1.4556    2.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157   -1.0675    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341   -1.8707    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8588   -2.1432   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938   -2.9292    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -3.5394    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0105   -3.1728   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1495   -3.9702   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0784   -4.1604   -0.9537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    2.0468   -1.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808    1.3161   -2.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543    2.1264   -2.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9767    3.5008   -1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    3.6614   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5595    2.4024    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207    1.1771    2.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138    1.3807    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1810   -0.1540    1.9177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    0.5907   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120   -0.2014    1.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023   -1.1405    2.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0587   -1.1943    3.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7808   -2.5679    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.6525   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403   -2.2648    1.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -1.7494   -1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2564   -4.6654    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0446   -3.1012    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -3.3704    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -2.7592   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2209   -4.3929    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8459    0.3557   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687    1.0858   -3.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5914    1.9385   -2.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1960    1.1755   -2.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.9165   -3.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466    2.3921   -1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    3.9701   -0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393    3.9657   -2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0956    3.9757   -1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    4.4913    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3154    1.7771   -0.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0095    2.7204    1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
all-trans-Retinaldehyde	ChEBI
all-trans-Retinene	ChEBI
all-trans-Vitamin a aldehyde	ChEBI
Retinaldehyde	ChEBI
Retinene	ChEBI
Vitamin a aldehyde	ChEBI
all-trans-Retinal	Kegg
Aldehyde, vitamin a	HMDB
Axerophthal	HMDB
11 cis Retinal	HMDB
11-cis-Retinal	HMDB
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal	HMDB
all-e-Retinal	HMDB
all-epsilon-Retinal	HMDB
alpha-Retinene	HMDB
e-Retinal	HMDB
epsilon-Retinal	HMDB
Retinene 1	HMDB
trans-Retinal	HMDB
trans-Vitamin a aldehyde	HMDB
Vitamin a1 aldehyde	HMDB

Chemical Formula

C₂₀H₂₈O

Average Molecular Weight

284.4357

Monoisotopic Molecular Weight

284.214015518

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Traditional Name

retinaldehyde

CAS Registry Number

116-31-4

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoid skeleton
Diterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinal (CHEBI:17898 )
Retinoids (C00376 )
Retinoids (LMPR01090002 )

Ontology

Not Available

Blood (HMDB: HMDB0001358)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0001358)

Hematocyte

Platelet (HMDB: HMDB0001358)

Cellular element

Platelet (HMDB: HMDB0001358)

Adrenal cortex (HMDB: HMDB0001358)

Organ substructure

Adrenal Cortex (HMDB: HMDB0001358)

Tissue

Epithelium

Epidermis (HMDB: HMDB0001358)

Muscle tissue

Skeletal Muscle (HMDB: HMDB0001358)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001358)

Source

Endogenous

Endogenous (HMDB: HMDB0001358)

Plant

Animal

Animal (HMDB: HMDB0001358)

Exogenous

Food

Food (HMDB: HMDB0001358)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001358)

Nutrient

Nutrient (HMDB: HMDB0001358)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001358)

Emulsifier (HMDB: HMDB0001358)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	63 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	170.463	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000451

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	6.62	ALOGPS
logP	4.86	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.87 m³·mol⁻¹	ChemAxon
Polarizability	35.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.059	31661259
DarkChem	[M-H]-	174.931	31661259
AllCCS	[M+H]+	174.537	32859911
AllCCS	[M-H]-	178.295	32859911
DeepCCS	[M+H]+	189.918	30932474
DeepCCS	[M-H]-	187.56	30932474
DeepCCS	[M-2H]-	221.477	30932474
DeepCCS	[M+Na]+	196.703	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	177.5	32859911
AllCCS	[M+Na]+	178.4	32859911
AllCCS	[M-H]-	178.3	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O	3063.2	Standard polar	33892256
Retinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O	2469.4	Standard non polar	33892256
Retinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O	2398.5	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 - Retinal GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2290000000-df9d2aa7545cc60a54f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinal 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Retinal 40V, Positive-QTOF	splash10-014i-9700000000-c2e22000dfae0765c367	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Retinal 10V, Positive-QTOF	splash10-03g0-0950000000-bccf87de037f98873f41	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Retinal 20V, Positive-QTOF	splash10-01t9-1910000000-5fe7643c395769c68286	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Retinal 40V, Positive-QTOF	splash10-014i-9700000000-fca532f917595376d653	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 10V, Positive-QTOF	splash10-000i-0490000000-f543f08fbaf94a2e3f8e	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 20V, Positive-QTOF	splash10-000i-3940000000-74f087cc812b3715e7ac	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 40V, Positive-QTOF	splash10-0fri-9830000000-72a5d01c6181340ad986	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 10V, Negative-QTOF	splash10-001i-0090000000-bad35938b77f181c29b9	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 20V, Negative-QTOF	splash10-001i-0090000000-1aadad0770df07f98436	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 40V, Negative-QTOF	splash10-00ko-4690000000-f624d342f88456375b9c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 10V, Positive-QTOF	splash10-00n3-1960000000-43f8c66f164764c37361	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 20V, Positive-QTOF	splash10-0609-3920000000-dbeab0a82b306761cf6a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 40V, Positive-QTOF	splash10-052f-7900000000-d2bb7c1aeeb87d8833d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 10V, Negative-QTOF	splash10-0a59-0090000000-2ec2f8f314943441fa15	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 20V, Negative-QTOF	splash10-0pb9-0190000000-312cebb17ccd0189ab4d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinal 40V, Negative-QTOF	splash10-000i-1590000000-b2551eac481c0c930a4d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Cortex
Epidermis
Fibroblasts
Intestine
Kidney
Lung
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.155 +/- 0.232 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FDB022576

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00376

BioCyc ID

RETINAL

BiGG ID

Not Available

Wikipedia Link

Retinal

METLIN ID

Not Available

PubChem Compound

638015

PDB ID

Not Available

ChEBI ID

17898

Food Biomarker Ontology

Not Available

VMH ID

RETINAL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Duhamel, Lucette; Duhamel, Pierre; Lecouve, Jean Pierre. A new synthesis of retinals. Journal of Chemical Research, Synopses (1986), (1), 34-5.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Chang M, Herbert WN: Retinal arteriolar occlusions following amniotic fluid embolism. Ophthalmology. 1984 Dec;91(12):1634-7. [PubMed:6521996 ]
Nguyen QD, Van Do D, Feke GT, Demirjian ZN, Lashkari K: Heparin-induced antiheparin-platelet antibody associated with retinal venous thrombosis. Ophthalmology. 2003 Mar;110(3):600-3. [PubMed:12623829 ]
Aarli JA, Mork SJ, Myrseth E, Larsen JL: Glioblastoma associated with multiple sclerosis: coincidence or induction? Eur Neurol. 1989;29(6):312-6. [PubMed:2691257 ]
Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential Binding to Glycotopes Among the Layers of Three Mammalian Retinal Neurons by Man-Containing N-linked Glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) Reactive Lectins. Neurochem Res. 2006 May 23;. [PubMed:16718528 ]
Jankowska R, Witkowska D, Porebska I, Kuropatwa M, Kurowska E, Gorczyca WA: Serum antibodies to retinal antigens in lung cancer and sarcoidosis. Pathobiology. 2004;71(6):323-8. [PubMed:15627843 ]
Weiland JD, Liu W, Humayun MS: Retinal prosthesis. Annu Rev Biomed Eng. 2005;7:361-401. [PubMed:16004575 ]
Fukushima A, Ueno H, Fujimoto S: Antigenic cross-reactivity between human T lymphotropic virus type I (HTLV-I) and retinal antigens recognized by T cells. Clin Exp Immunol. 1994 Mar;95(3):459-64. [PubMed:8137541 ]
Bradbury MW, Lightman SL: The blood-brain interface. Eye (Lond). 1990;4 ( Pt 2):249-54. [PubMed:2199234 ]
Bringmann A, Reichenbach A, Wiedemann P: Pathomechanisms of cystoid macular edema. Ophthalmic Res. 2004 Sep-Oct;36(5):241-9. [PubMed:15583429 ]
Wu WC, Lai CC, Liu JH, Singh T, Li LM, Peumans WJ, Van Damme EJ, Wu AM: Differential binding to glycotopes among the layers of three mammalian retinal neurons by man-containing N-linked glycan, T(alpha) (Galbeta1-3GalNAcalpha1-), Tn (GalNAcalpha1-Ser/Thr) and I (beta)/II (beta) (Galbeta1-3/4GlcNAcbeta-) reactive lectins. Neurochem Res. 2006 May;31(5):619-28. Epub 2006 May 23. [PubMed:16770733 ]
Yamashiro K, Tsujikawa A, Ishida S, Usui T, Kaji Y, Honda Y, Ogura Y, Adamis AP: Platelets accumulate in the diabetic retinal vasculature following endothelial death and suppress blood-retinal barrier breakdown. Am J Pathol. 2003 Jul;163(1):253-9. [PubMed:12819029 ]
Ramirez JM, Ramirez AI, Salazar JJ, de Hoz R, Trivino A: Changes of astrocytes in retinal ageing and age-related macular degeneration. Exp Eye Res. 2001 Nov;73(5):601-15. [PubMed:11747361 ]

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Retinal dehydrogenase 1

General function:: Involved in oxidoreductase activity
Specific function:: Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name:: ALDH1A1
Uniprot ID:: P00352
Molecular weight:: 54861.44

Reactions

Retinal + NAD + Water → 13-cis-Retinoic acid + NADH	details
Retinal + NAD + Water → all-trans-Retinoic acid + NADH + Hydrogen Ion	details

Enzyme Details

2. Retinal dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:: ALDH1A2
Uniprot ID:: O94788
Molecular weight:: 54672.24

Reactions

Retinal + NAD + Water → 13-cis-Retinoic acid + NADH	details
Retinal + NAD + Water → all-trans-Retinoic acid + NADH + Hydrogen Ion	details

Enzyme Details

3. 11-cis retinol dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-retinol and 13-cis-retinol, but not all-trans-retinol. Active in the presence of NAD as cofactor but not in the presence of NADP.
Gene Name:: RDH5
Uniprot ID:: Q92781
Molecular weight:: 34978.425

Enzyme Details

4. Alcohol dehydrogenase 4

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH4
Uniprot ID:: P08319
Molecular weight:: 40221.335

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

5. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

6. Alcohol dehydrogenase 1B

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1B
Uniprot ID:: P00325
Molecular weight:: 39835.17

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

7. Alcohol dehydrogenase class 4 mu/sigma chain

General function:: Involved in zinc ion binding
Specific function:: Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:: ADH7
Uniprot ID:: P40394
Molecular weight:: 41480.985

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

8. Alcohol dehydrogenase 1A

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1A
Uniprot ID:: P07327
Molecular weight:: 39858.37

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

9. Alcohol dehydrogenase 6

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH6
Uniprot ID:: P28332
Molecular weight:: 39072.275

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Enzyme Details

10. Alcohol dehydrogenase 1C

General function:: Involved in zinc ion binding
Specific function:: Not Available
Gene Name:: ADH1C
Uniprot ID:: P00326
Molecular weight:: 39867.27

Reactions

Vitamin A + NAD → Retinal + NADH + Hydrogen Ion	details

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for Retinal (HMDB0001358)

MOL for HMDB0001358 (Retinal)

3D MOL for HMDB0001358 (Retinal)

3D SDF for HMDB0001358 (Retinal)

3D-SDF for HMDB0001358 (Retinal)

PDB for HMDB0001358 (Retinal)

3D PDB for HMDB0001358 (Retinal)

SMILES for HMDB0001358 (Retinal)

INCHI for HMDB0001358 (Retinal)

Structure for HMDB0001358 (Retinal)

3D Structure for HMDB0001358 (Retinal)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

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