NP-MRD: Showing NP-Card for 11-cis-Retinaldehyde (NP0001147)

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Record Information

Version

1.0

Created at

2006-05-22 14:17:38 UTC

Updated at

2021-06-29 00:47:23 UTC

NP-MRD ID

NP0001147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-cis-Retinaldehyde

Description

11-Cis-retinal is a retinal having 2E,4Z,6E,8E-double bond geometry. It has a role as a chromophore, a human metabolite and a mouse metabolite. It is a diterpene derived from the carotenoid vitamin A which functions as the active component of the visual cycle. It is the prosthetic group of rhodopsin. When stimulated by visible light, rhodopsin transforms this cis-isomer of retinal to the trans-isomer (11-trans-retinal). This transformation straightens-out the bend of the retinal molecule and causes a change in the shape of rhodopsin triggering the visual process. A series of energy-requiring enzyme-catalyzed reactions convert the 11-trans-retinal back to the cis-isomer. 11-Cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-Cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-Cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly.

Structure

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

HMDB0002152
     RDKit          3D
11-cis-Retinaldehyde
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.1860   -0.2385    3.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132   -0.5983    1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -0.5145    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300   -0.0640    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    0.0974    0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266    0.5712    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.8420    2.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    0.7290    0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737    1.1809    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.3173    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.0678   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036    0.4788   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1387    1.3344   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5390    1.1361   -2.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7690    1.4482   -3.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557   -0.8558   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -1.9461   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.3749   -1.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.4079   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -0.8065   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846   -1.0454    1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.8374    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.8596    3.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.3789    3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    0.1882    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.1197   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -0.1075    3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    1.6055    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    1.0224    3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    0.5027   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266    1.4350    2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    1.6929    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6004   -0.4944   -1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628    0.0569   -2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.0914   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8581    1.7265   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9899    0.7840   -3.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -2.2554   -0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.7090   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -2.8892   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    0.6962   -2.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941    1.2246   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.1299   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -2.5117   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -1.1844   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829    0.2513   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9654   -1.3413   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9614   -2.0994    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5248   -0.4396    1.7983 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
   -0.7145    0.4125    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
    0.7145    0.4125    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
    0.0000   -0.8250    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
    0.4125    1.5395    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
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    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
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  8  1  0  0  0  0
  4  3  2  0  0  0  0
 20  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  6  3  1  0  0  0  0
 16  6  1  0  0  0  0
  7  6  1  0  0  0  0
  8 19  2  0  0  0  0
 17  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 14  1  0  0  0  0
 14 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 21  2  0  0  0  0
 14 15  1  0  0  0  0
 19 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001147

> <DATABASE_NAME>
NP-MRD

> <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-IOUUIBBYSA-N

> <FORMULA>
C20H28O

> <MOLECULAR_WEIGHT>
284.4357

> <EXACT_MASS>
284.214015518

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.820546205282355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z,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>
96.86540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-cis-retinal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002152
     RDKit          3D
11-cis-Retinaldehyde
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.1860   -0.2385    3.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132   -0.5983    1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -0.5145    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300   -0.0640    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    0.0974    0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266    0.5712    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.8420    2.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    0.7290    0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737    1.1809    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.3173    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.0678   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036    0.4788   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1387    1.3344   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5390    1.1361   -2.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7690    1.4482   -3.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557   -0.8558   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -1.9461   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.3749   -1.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.4079   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -0.8065   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846   -1.0454    1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.8374    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.8596    3.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.3789    3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    0.1882    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.1197   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -0.1075    3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    1.6055    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    1.0224    3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    0.5027   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266    1.4350    2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    1.6929    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6004   -0.4944   -1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628    0.0569   -2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.0914   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8581    1.7265   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9899    0.7840   -3.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -2.2554   -0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.7090   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -2.8892   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    0.6962   -2.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941    1.2246   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.1299   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -2.5117   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -1.1844   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829    0.2513   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9654   -1.3413   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9614   -2.0994    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5248   -0.4396    1.7983 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      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.770   2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    5                                                       
CONECT    3    8    4    6                                                  
CONECT    4    3   20    5                                                  
CONECT    5    2    4                                                       
CONECT    6    1    3   16    7                                             
CONECT    7    6                                                            
CONECT    8    3   19                                                       
CONECT    9   17   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   14                                                       
CONECT   12   14   13                                                       
CONECT   13   12   21                                                       
CONECT   14   11   12   15                                                  
CONECT   15   14                                                            
CONECT   16    6                                                            
CONECT   17    9   19   18                                                  
CONECT   18   17                                                            
CONECT   19    8   17                                                       
CONECT   20    4                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0002152
HETATM    1  C1  UNL     1      -3.186  -0.239   3.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.413  -0.598   1.621  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.410  -0.514   0.735  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.130  -0.064   1.238  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.018   0.097   0.576  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.227   0.571   1.240  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.184   0.842   2.673  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.337   0.729   0.540  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.574   1.181   1.102  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.660   1.317   0.424  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.909   1.068  -0.955  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.004   0.479  -1.921  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.139   1.334  -1.430  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.539   1.136  -2.808  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.769   1.448  -3.044  1.00  0.00           O  
HETATM   16  C15 UNL     1      -2.556  -0.856  -0.691  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.565  -1.946  -1.018  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.257   0.375  -1.520  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.926  -1.408  -1.027  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.037  -0.807  -0.239  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.785  -1.045   1.235  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.368  -0.837   3.498  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.949   0.860   3.119  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.129  -0.379   3.597  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.047   0.188   2.314  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.014  -0.120  -0.475  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.748  -0.107   3.140  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.400   1.605   2.942  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.120   1.022   3.191  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.167   0.503  -0.497  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.627   1.435   2.161  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.527   1.693   1.052  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.600  -0.494  -1.505  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.563   0.057  -2.831  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.183   1.091  -2.264  1.00  0.00           H  
HETATM   36  H15 UNL     1       6.858   1.727  -0.695  1.00  0.00           H  
HETATM   37  H16 UNL     1       5.990   0.784  -3.632  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.940  -2.255  -0.150  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.981  -1.709  -1.926  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.141  -2.889  -1.267  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.212   0.696  -2.011  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.894   1.225  -0.924  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.500   0.130  -2.287  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.922  -2.512  -0.946  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.107  -1.184  -2.112  1.00  0.00           H  
HETATM   46  H25 UNL     1      -5.183   0.251  -0.469  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.965  -1.341  -0.494  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.961  -2.099   1.479  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.525  -0.440   1.798  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

HMDB0002152
     RDKit          3D
11-cis-Retinaldehyde
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.1860   -0.2385    3.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132   -0.5983    1.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4098   -0.5145    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1300   -0.0640    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0183    0.0974    0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266    0.5712    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1837    0.8420    2.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3366    0.7290    0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5737    1.1809    1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.3173    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    1.0678   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036    0.4788   -1.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1387    1.3344   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5390    1.1361   -2.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7690    1.4482   -3.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5557   -0.8558   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -1.9461   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2570    0.3749   -1.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.4079   -1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0366   -0.8065   -0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7846   -1.0454    1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3676   -0.8374    3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487    0.8596    3.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1285   -0.3789    3.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0473    0.1882    2.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.1197   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -0.1075    3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    1.6055    2.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204    1.0224    3.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673    0.5027   -0.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266    1.4350    2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    1.6929    1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6004   -0.4944   -1.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628    0.0569   -2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.0914   -2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8581    1.7265   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9899    0.7840   -3.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -2.2554   -0.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.7090   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -2.8892   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    0.6962   -2.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941    1.2246   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.1299   -2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222   -2.5117   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1075   -1.1844   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1829    0.2513   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9654   -1.3413   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9614   -2.0994    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5248   -0.4396    1.7983 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 NMR Assignments

Synonyms

Value	Source
(2E,4Z,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal	ChEBI
11-cis-Retinene	ChEBI
11-cis-Vitamin a aldehyde	ChEBI
11-cis-Retinal	HMDB
cis-11-Retinal	HMDB
11 cis Retinal	HMDB
Retinaldehyde	HMDB
Retinene	HMDB
Retinal	HMDB
Aldehyde, vitamin a	HMDB
Vitamin a aldehyde	HMDB
Axerophthal	HMDB

Chemical Formula

C₂₀H₂₈O

Average Mass

284.4357 Da

Monoisotopic Mass

284.21402 Da

IUPAC Name

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

Traditional Name

11-cis-retinal

CAS Registry Number

564-87-4

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-IOUUIBBYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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:16066 )
Retinoids (C02110 )
Retinoids (LMPR01090003 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	63.5 - 64.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted 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	34.82 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

External Links

HMDB ID

HMDB0002152

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022871

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6513

PubChem Compound

5280490

PDB ID

Not Available

ChEBI ID

16066

Good Scents ID

Not Available

References

General References

Bankson DD, Russell RM, Sadowski JA: Determination of retinyl esters and retinol in serum or plasma by normal-phase liquid chromatography: method and applications. Clin Chem. 1986 Jan;32(1 Pt 1):35-40. [PubMed:3940733 ]
Futterman S, Saari JC: Occurrence of 11-cis-retinal-binding protein restricted to the retina. Invest Ophthalmol Vis Sci. 1977 Aug;16(8):768-71. [PubMed:560359 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
Edwards RB, Adler AJ: IRBP enhances removal of 11- cis -retinaldehyde from isolated RPE membranes. Exp Eye Res. 2000 Feb;70(2):235-45. doi: 10.1006/exer.1999.0781. [PubMed:10655150 ]
Shaw NS, Noy N: Interphotoreceptor retinoid-binding protein contains three retinoid binding sites. Exp Eye Res. 2001 Feb;72(2):183-90. doi: 10.1006/exer.2000.0945. [PubMed:11161734 ]

Showing NP-Card for 11-cis-Retinaldehyde (NP0001147)

MOL for NP0001147 (11-cis-Retinaldehyde)

3D MOL for NP0001147 (11-cis-Retinaldehyde)

3D SDF for NP0001147 (11-cis-Retinaldehyde)

3D-SDF for NP0001147 (11-cis-Retinaldehyde)

PDB for NP0001147 (11-cis-Retinaldehyde)

3D PDB for NP0001147 (11-cis-Retinaldehyde)

SMILES for NP0001147 (11-cis-Retinaldehyde)

INCHI for NP0001147 (11-cis-Retinaldehyde)

Structure for NP0001147 (11-cis-Retinaldehyde)

3D Structure for NP0001147 (11-cis-Retinaldehyde)