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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:42:26 UTC

Update Date

2022-03-07 02:54:36 UTC

HMDB ID

HMDB0035695

Secondary Accession Numbers

HMDB35695

Metabolite Identification

Common Name

Vitamin A2 aldehyde

Description

Vitamin A2 aldehyde, also known as 3-dehydroretinal or retinene 2, 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. Thus, vitamin A2 aldehyde is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on Vitamin A2 aldehyde.

Structure

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

HMDB0035695
     RDKit          3D
Vitamin A2 aldehyde
 47 47  0  0  0  0  0  0  0  0999 V2000
   -3.3175    0.3169    3.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8320    0.1011    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041   -0.0183    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687    0.0759    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.0165    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    0.0940    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    0.3120    1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -0.0036   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    0.0998   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.0049   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4889    0.0769   -0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200    0.3058    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -0.0470   -1.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375    0.0176   -1.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4361   -0.1099   -2.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -0.2369   -0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.5675   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485    0.8769   -1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -0.3010   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7570   -0.1625    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2496    0.0187    1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -0.6022    3.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    1.2030    3.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758    0.5144    3.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2659    0.2341    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -0.1715   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.2073    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -0.6011    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893    0.5045    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.1660   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.2475    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -0.1654   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.8475    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417    0.9151    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2219   -0.6531    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659   -0.2090   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2219    0.1666   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.9727   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252   -2.2707   -1.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4171   -1.4100   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253    1.4514   -2.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.6030   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624    0.4428   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1733   -1.3235   -1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229    0.4660   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654   -0.2052    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.1197    2.3051 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  2  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
 21 47  1  0
M  END


  Mrv0541 05061308392D          

 21 21  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 12 11  2  0  0  0  0
 14  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16  1  1  0  0  0  0
 16  8  2  0  0  0  0
 16 11  1  0  0  0  0
 17  2  1  0  0  0  0
 17  9  1  0  0  0  0
 17 13  2  0  0  0  0
 18  3  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  2  0  0  0  0
 20  4  1  0  0  0  0
 20  5  1  0  0  0  0
 20 14  1  0  0  0  0
 20 19  1  0  0  0  0
 21 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035695

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C=CCC1(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,15H,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

> <INCHI_KEY>
QHNVWXUULMZJKD-OVSJKPMPSA-N

> <FORMULA>
C20H26O

> <MOLECULAR_WEIGHT>
282.4198

> <EXACT_MASS>
282.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
35.17278706476937

> <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-trimethylcyclohexa-1,3-dien-1-yl)nona-2,4,6,8-tetraenal

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
4.4938298020000005

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.061304751803082

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
97.98200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-retinene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035695
     RDKit          3D
Vitamin A2 aldehyde
 47 47  0  0  0  0  0  0  0  0999 V2000
   -3.3175    0.3169    3.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8320    0.1011    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041   -0.0183    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687    0.0759    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.0165    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    0.0940    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    0.3120    1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -0.0036   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    0.0998   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.0049   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4889    0.0769   -0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200    0.3058    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -0.0470   -1.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375    0.0176   -1.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4361   -0.1099   -2.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -0.2369   -0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.5675   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485    0.8769   -1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -0.3010   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7570   -0.1625    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2496    0.0187    1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -0.6022    3.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    1.2030    3.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758    0.5144    3.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2659    0.2341    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -0.1715   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.2073    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -0.6011    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893    0.5045    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.1660   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.2475    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -0.1654   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.8475    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417    0.9151    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2219   -0.6531    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659   -0.2090   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2219    0.1666   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.9727   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252   -2.2707   -1.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4171   -1.4100   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253    1.4514   -2.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.6030   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624    0.4428   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1733   -1.3235   -1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229    0.4660   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654   -0.2052    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.1197    2.3051 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  2  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
 21 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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   20                                                            
CONECT    5   20                                                            
CONECT    6    8    9                                                       
CONECT    7   10   14                                                       
CONECT    8    6   16                                                       
CONECT    9    6   17                                                       
CONECT   10    7   18                                                       
CONECT   11   12   16                                                       
CONECT   12   11   19                                                       
CONECT   13   15   17                                                       
CONECT   14    7   20                                                       
CONECT   15   13   21                                                       
CONECT   16    1    8   11                                                  
CONECT   17    2    9   13                                                  
CONECT   18    3   10   19                                                  
CONECT   19   12   18   20                                                  
CONECT   20    4    5   14   19                                             
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0035695
HETATM    1  C1  UNL     1      -3.318   0.317   3.085  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.832   0.101   1.692  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.004  -0.018   0.642  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.569   0.076   0.943  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.622  -0.017   0.050  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.795   0.094   0.470  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.063   0.312   1.895  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.736  -0.004  -0.445  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.137   0.100  -0.067  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.064  -0.005  -1.033  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.489   0.077  -0.818  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.020   0.306   0.538  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.302  -0.047  -1.853  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.737   0.018  -1.748  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.436  -0.110  -2.805  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.477  -0.237  -0.736  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.873  -1.568  -1.194  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.949   0.877  -1.656  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.939  -0.301  -0.967  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.757  -0.163   0.227  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.250   0.019   1.422  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.824  -0.602   3.473  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.653   1.203   3.136  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.176   0.514   3.728  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.266   0.234   1.996  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.818  -0.171  -0.995  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.481   1.207   2.289  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.750  -0.601   2.486  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.089   0.505   2.180  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.462  -0.166  -1.511  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.517   0.247   0.911  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.712  -0.165  -2.068  1.00  0.00           H  
HETATM   33  H12 UNL     1       6.999   0.848   0.549  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.342   0.915   1.187  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.222  -0.653   1.078  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.866  -0.209  -2.855  1.00  0.00           H  
HETATM   37  H16 UNL     1       8.222   0.167  -0.823  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.190  -1.973  -0.446  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.725  -2.271  -1.349  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.417  -1.410  -2.186  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.825   1.451  -2.081  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.325   1.603  -1.131  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.462   0.443  -2.546  1.00  0.00           H  
HETATM   44  H23 UNL     1      -5.173  -1.324  -1.414  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.223   0.466  -1.752  1.00  0.00           H  
HETATM   46  H25 UNL     1      -6.865  -0.205   0.177  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.909   0.120   2.305  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   21   46
CONECT   21   47
END

HMDB0035695
     RDKit          3D
Vitamin A2 aldehyde
 47 47  0  0  0  0  0  0  0  0999 V2000
   -3.3175    0.3169    3.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8320    0.1011    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041   -0.0183    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5687    0.0759    0.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.0165    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    0.0940    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0629    0.3120    1.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -0.0036   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1369    0.0998   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.0049   -1.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4889    0.0769   -0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0200    0.3058    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -0.0470   -1.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375    0.0176   -1.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4361   -0.1099   -2.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -0.2369   -0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.5675   -1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485    0.8769   -1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -0.3010   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7570   -0.1625    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2496    0.0187    1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237   -0.6022    3.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    1.2030    3.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758    0.5144    3.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2659    0.2341    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -0.1715   -0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810    1.2073    2.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -0.6011    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893    0.5045    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -0.1660   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    0.2475    0.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7117   -0.1654   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.8475    0.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417    0.9151    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2219   -0.6531    1.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659   -0.2090   -2.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2219    0.1666   -0.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -1.9727   -0.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252   -2.2707   -1.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4171   -1.4100   -2.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253    1.4514   -2.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.6030   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624    0.4428   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1733   -1.3235   -1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229    0.4660   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8654   -0.2052    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9094    0.1197    2.3051 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  2  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
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2,4,6,8-nonatetraenal	ChEBI
3,4-Didehydroretinal	ChEBI
3-Dehydroretinal	ChEBI
3-Dehydroretinaldehyde	ChEBI
all-trans-3,4-Dehydroretinal	ChEBI
all-trans-3,4-Didehydroretinal	ChEBI
Dehydroretinal	ChEBI
Dehydroretinaldehyd	ChEBI
Dehydroretinaldehyde	ChEBI
Retinene 2	ChEBI
trans-3-Dehydroretinal	ChEBI
alpha-Retinene	Kegg
all-trans-3-Dehydroretinal	Kegg
a-Retinene	Generator
Α-retinene	Generator
Vitamin a2 aldehyde	ChEBI
all-trans-Dehydroretinal	HMDB
Didehydroretinal	HMDB
Retinene2	HMDB

Chemical Formula

C₂₀H₂₆O

Average Molecular Weight

282.4198

Monoisotopic Molecular Weight

282.198365454

IUPAC Name

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

Traditional Name

α-retinene

CAS Registry Number

472-87-7

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)C=CCC1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H26O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6-13,15H,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+

InChI Key

QHNVWXUULMZJKD-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

retinals (CHEBI:28537 )
Retinoids (C05918 )
Retinoids (LMPR01090006 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0035695)
Cell membrane (HMDB: HMDB0035695)

Cellular substructure

Extracellular (HMDB: HMDB0035695)
Membrane (HMDB: HMDB0035695)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035695)

Source

Endogenous

Endogenous (HMDB: HMDB0035695)

Animal

Animal (HMDB: HMDB0035695)

Exogenous

Food

Food (HMDB: HMDB0035695)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035695)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035695)

Cellular process

Cell signaling (HMDB: HMDB0035695)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035695)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035695)

Nutrient

Nutrient (HMDB: HMDB0035695)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035695)

Emulsifier (HMDB: HMDB0035695)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	77 - 78 °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	0.0078 g/L	ALOGPS
logP	6.23	ALOGPS
logP	4.49	ChemAxon
logS	-4.6	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	97.98 m³·mol⁻¹	ChemAxon
Polarizability	35.17 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]+	174.039	31661259
DarkChem	[M-H]-	174.977	31661259
DeepCCS	[M+H]+	187.806	30932474
DeepCCS	[M-H]-	185.449	30932474
DeepCCS	[M-2H]-	219.664	30932474
DeepCCS	[M+Na]+	194.891	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vitamin A2 aldehyde	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C=CCC1(C)C)=C/C=O	3084.6	Standard polar	33892256
Vitamin A2 aldehyde	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C=CCC1(C)C)=C/C=O	2465.8	Standard non polar	33892256
Vitamin A2 aldehyde	C\C(\C=C\C=C(/C)\C=C\C1=C(C)C=CCC1(C)C)=C/C=O	2360.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A2 aldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3390000000-b43234a3e9e80e42069a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A2 aldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitamin A2 aldehyde 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 - Vitamin A2 aldehyde 10V, Positive-QTOF	splash10-001i-0390000000-e4f7df4aafbf3afb8027	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 20V, Positive-QTOF	splash10-000b-3950000000-598ead96d05f7aaebc3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 40V, Positive-QTOF	splash10-0gb9-9630000000-846af33809ab9788af6c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 10V, Negative-QTOF	splash10-001i-0090000000-9168b729b43a5a65ba9d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 20V, Negative-QTOF	splash10-001i-0090000000-1b18d37b61eaa42c0546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 40V, Negative-QTOF	splash10-00lf-4690000000-8847b5a91089f800c819	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 10V, Positive-QTOF	splash10-0089-0890000000-d223586cb342184a9bb7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 20V, Positive-QTOF	splash10-0609-1920000000-a08bf88e2ad686e79906	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 40V, Positive-QTOF	splash10-0ktf-6910000000-d693220dd31ea38e6bb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 10V, Negative-QTOF	splash10-0ue9-0090000000-05c80fceaf05a3c9092a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 20V, Negative-QTOF	splash10-0udi-0190000000-2ae88f39d78c4123e339	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitamin A2 aldehyde 40V, Negative-QTOF	splash10-000i-1390000000-1f2616fe59f814913203	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

FDB014413

KNApSAcK ID

Not Available

Chemspider ID

4444397

KEGG Compound ID

C05918

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280866

PDB ID

Not Available

ChEBI ID

28537

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 Vitamin A2 aldehyde (HMDB0035695)

MOL for HMDB0035695 (Vitamin A2 aldehyde)

3D MOL for HMDB0035695 (Vitamin A2 aldehyde)

3D SDF for HMDB0035695 (Vitamin A2 aldehyde)

3D-SDF for HMDB0035695 (Vitamin A2 aldehyde)

PDB for HMDB0035695 (Vitamin A2 aldehyde)

3D PDB for HMDB0035695 (Vitamin A2 aldehyde)

SMILES for HMDB0035695 (Vitamin A2 aldehyde)

INCHI for HMDB0035695 (Vitamin A2 aldehyde)

Structure for HMDB0035695 (Vitamin A2 aldehyde)

3D Structure for HMDB0035695 (Vitamin A2 aldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra