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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-06-18 12:29:07 UTC

Update Date

2022-03-07 02:51:25 UTC

HMDB ID

HMDB0012452

Secondary Accession Numbers

HMDB0061095
HMDB12452
HMDB61095

Metabolite Identification

Common Name

all-trans-18-Hydroxyretinoic acid

Description

all-trans-18-Hydroxyretinoic acid, also known as 18-hydroxyretinoic acid, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-18-Hydroxyretinoic acid is considered to be a practically insoluble (in water) and a weakly acidic compound. all-trans-18-Hydroxyretinoic acid is an isoprenoid lipid molecule. Within a cell, all-trans-18-hydroxyretinoic acid is primarily located in the extracellular space and near the membrane. 18-Hydroxyretinoic acid is a metabolite of tretinoin. Tretinoin is the acid form of vitamin A and is also known as all-trans retinoic acid or ATRA. It is a drug commonly used to treat acne vulgaris and keratosis pilaris. It is available as a cream or gel (brand names Aberela, Airol, Renova, Atralin, Retin-A, Avita, Retacnyl, Refissa, or Stieva-A). It is also used to treat acute promyelocytic leukemia (APL) and is sold for this indication by Roche under the brand name Vesanoid. It is also available as a generic. (Wikipedia)

Structure

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

HMDB0012452
     RDKit          3D
all-trans-18-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    0.9995   -1.1967   -1.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.4193   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.1457    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568   -0.0602   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.4351   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    0.0890   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890   -0.7208   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -1.8986   -2.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    0.5087   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1339    1.9974   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2492    2.3500    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310    1.2626    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    1.9770    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.3443    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.1820    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -0.6616    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316   -0.4075    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714   -0.8551    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0601   -1.6556   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.5279    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   -0.9159    1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -0.5523    2.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5409   -1.6621    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -0.5703   -2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -2.0076   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9329   -1.6908   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.6727    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -0.6584   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.9937   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929   -0.2351   -3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841   -2.5153   -2.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772   -0.0252   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.3682   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1591    2.4142   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508    2.4803   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570    2.6248    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251    3.2421    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    2.5482    1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892    1.4168    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927    2.8433    2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.2727    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    0.7111    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0398   -0.6987    1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.3998    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562   -1.2351   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    0.2002    1.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5230   -2.6352   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959   -1.9127   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8414   -1.1347   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3326    0.0638    2.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -1.3397   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END

  Mrv1652307161916582D          

 23 23  0  0  0  0            999 V2000
 9997.871610000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5856 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299610000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0146 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.730310000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4439 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.157510000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8711 9999.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.584710000.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3003 9999.9695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.584710001.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.157510001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.299610001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.445610001.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.731610001.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4399 9998.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9698 9999.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.444310000.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7298 9999.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7298 9999.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4443 9998.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1588 9999.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1588 9999.9701    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 13  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 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 17  1  0  0  0  0
 22 16  1  0  0  0  0
 18 14  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012452

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+

> <INCHI_KEY>
XSJOIRFEYHJNAW-FCKHSPHMSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.46980704772441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
4.79

> <JCHEM_LOGP>
3.7335965543333325

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.25421877581346

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.996647812346559

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8128047748082965

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
99.56549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012452
     RDKit          3D
all-trans-18-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    0.9995   -1.1967   -1.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.4193   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.1457    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568   -0.0602   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.4351   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    0.0890   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890   -0.7208   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -1.8986   -2.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    0.5087   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1339    1.9974   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2492    2.3500    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310    1.2626    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    1.9770    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.3443    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.1820    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -0.6616    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316   -0.4075    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714   -0.8551    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0601   -1.6556   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.5279    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   -0.9159    1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -0.5523    2.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5409   -1.6621    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -0.5703   -2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -2.0076   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9329   -1.6908   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.6727    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -0.6584   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.9937   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929   -0.2351   -3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841   -2.5153   -2.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772   -0.0252   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.3682   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1591    2.4142   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508    2.4803   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570    2.6248    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251    3.2421    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    2.5482    1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892    1.4168    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927    2.8433    2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.2727    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    0.7111    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0398   -0.6987    1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.3998    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562   -1.2351   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    0.2002    1.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5230   -2.6352   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959   -1.9127   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8414   -1.1347   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3326    0.0638    2.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -1.3397   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 16-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JUL-19         0                                  
HETATM    1  C   UNK     0    8662.6948667.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0268666.610   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.3598667.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.6948666.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.0308667.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.3628666.610   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.6948667.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.0268666.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.3588667.381   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8674.6948666.610   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8673.3588668.921   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8670.6948668.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3598668.921   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.0328668.921   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8658.6998669.687   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8661.8888663.627   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.8778665.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.0298667.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8658.6968666.611   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8658.6968665.071   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.0298664.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8661.3638665.071   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.3638666.611   0.000  0.00  0.00           C+0
CONECT    1    2   23                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7                                                            
CONECT   13    3                                                            
CONECT   14   15   18                                                       
CONECT   15   14                                                            
CONECT   16   22                                                            
CONECT   17   22                                                            
CONECT   18   19   23   14                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   17   16                                             
CONECT   23   18   22    1                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0012452
HETATM    1  C1  UNL     1       0.999  -1.197  -1.519  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.936  -0.419  -0.276  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.385   0.146   0.165  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.457  -0.060  -0.564  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.780   0.435  -0.243  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.766   0.089  -1.121  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.489  -0.721  -2.298  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.288  -1.899  -2.163  1.00  0.00           O  
HETATM    9  C8  UNL     1      -5.197   0.509  -0.888  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.134   1.997  -0.645  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.249   2.350   0.471  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.231   1.263   0.867  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.211   1.977   1.703  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.993   0.344   1.844  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.962  -0.182   0.482  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.308  -0.662   0.187  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.332  -0.407   0.973  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.671  -0.855   0.729  1.00  0.00           C  
HETATM   19  C18 UNL     1       6.060  -1.656  -0.429  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.621  -0.528   1.605  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.016  -0.916   1.477  1.00  0.00           C  
HETATM   22  O2  UNL     1       8.841  -0.552   2.369  1.00  0.00           O  
HETATM   23  O3  UNL     1       8.541  -1.662   0.448  1.00  0.00           O  
HETATM   24  H1  UNL     1       0.726  -0.570  -2.403  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.217  -2.008  -1.468  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.933  -1.691  -1.742  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.383   0.673   1.066  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.278  -0.658  -1.473  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.515  -0.994  -2.596  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.993  -0.235  -3.220  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.084  -2.515  -2.912  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.677  -0.025  -0.075  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.714   0.368  -1.867  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.159   2.414  -0.457  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.751   2.480  -1.589  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.857   2.625   1.366  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.625   3.242   0.202  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.534   2.548   1.058  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.789   1.417   2.533  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.793   2.843   2.231  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.415   0.273   2.810  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.002   0.711   2.065  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.040  -0.699   1.474  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.850   0.400   1.389  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.456  -1.235  -0.702  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.090   0.200   1.878  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.523  -2.635  -0.139  1.00  0.00           H  
HETATM   48  H25 UNL     1       5.196  -1.913  -1.041  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.841  -1.135  -1.053  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.333   0.064   2.465  1.00  0.00           H  
HETATM   51  H28 UNL     1       9.336  -1.340  -0.121  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   15   15
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6    6   12
CONECT    6    7    9
CONECT    7    8   29   30
CONECT    8   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   14
CONECT   13   38   39   40
CONECT   14   41   42   43
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   46
CONECT   18   19   20   20
CONECT   19   47   48   49
CONECT   20   21   50
CONECT   21   22   22   23
CONECT   23   51
END

HMDB0012452
     RDKit          3D
all-trans-18-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    0.9995   -1.1967   -1.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.4193   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3851    0.1457    0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4568   -0.0602   -0.5642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805    0.4351   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    0.0890   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890   -0.7208   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -1.8986   -2.1632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1966    0.5087   -0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1339    1.9974   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2492    2.3500    0.4714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2310    1.2626    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115    1.9770    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.3443    1.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621   -0.1820    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3077   -0.6616    0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3316   -0.4075    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714   -0.8551    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0601   -1.6556   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6205   -0.5279    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   -0.9159    1.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8406   -0.5523    2.3691 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5409   -1.6621    0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -0.5703   -2.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2168   -2.0076   -1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9329   -1.6908   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827    0.6727    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775   -0.6584   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.9937   -2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929   -0.2351   -3.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841   -2.5153   -2.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772   -0.0252   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.3682   -1.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1591    2.4142   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508    2.4803   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570    2.6248    1.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251    3.2421    0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    2.5482    1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7892    1.4168    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7927    2.8433    2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4148    0.2727    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017    0.7111    2.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0398   -0.6987    1.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8502    0.3998    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562   -1.2351   -0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0903    0.2002    1.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5230   -2.6352   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959   -1.9127   -1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8414   -1.1347   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3326    0.0638    2.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3362   -1.3397   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
18-Hydroxy-all-trans-retinoic acid	ChEBI
18-Hydroxyretinoic acid	ChEBI
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	ChEBI
18-Hydroxy-all-trans-retinoate	Generator
18-Hydroxyretinoate	Generator
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoate	Generator
all-trans-18-Hydroxyretinoate	Generator
rac-18-Hydroxy-all-trans-retinoate	HMDB
rac-18-Hydroxy-all-trans-retinoic acid	HMDB
all-trans-18-Hydroxyretinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

CAS Registry Number

63531-93-1

SMILES

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

InChI Identifier

InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+

InChI Key

XSJOIRFEYHJNAW-FCKHSPHMSA-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

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:80657 )
Retinoids (C16679 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0012452)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012452)

Organ

Kidney (HMDB: HMDB0012452)
Liver (HMDB: HMDB0012452)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012452)

Source

Endogenous

Endogenous (HMDB: HMDB0012452)

Animal

Animal (HMDB: HMDB0012452)

Exogenous

Food

Food (HMDB: HMDB0012452)

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0012452)

Process

Role

Biological role

Energy source (HMDB: HMDB0012452)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012452)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	4.79	ALOGPS
logP	3.73	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	37.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.938	31661259
DarkChem	[M-H]-	181.807	31661259
DeepCCS	[M+H]+	202.974	30932474
DeepCCS	[M-H]-	200.532	30932474
DeepCCS	[M-2H]-	234.994	30932474
DeepCCS	[M+Na]+	210.739	30932474
AllCCS	[M+H]+	180.7	32859911
AllCCS	[M+H-H2O]+	177.6	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	183.6	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	185.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
all-trans-18-Hydroxyretinoic acid	C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	3956.5	Standard polar	33892256
all-trans-18-Hydroxyretinoic acid	C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2629.4	Standard non polar	33892256
all-trans-18-Hydroxyretinoic acid	C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2784.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
all-trans-18-Hydroxyretinoic acid,1TMS,isomer #1	CC(/C=C/C1=C(CO[Si](C)(C)C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O	2860.0	Semi standard non polar	33892256
all-trans-18-Hydroxyretinoic acid,1TMS,isomer #2	CC(/C=C/C1=C(CO)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C	2850.1	Semi standard non polar	33892256
all-trans-18-Hydroxyretinoic acid,2TMS,isomer #1	CC(/C=C/C1=C(CO[Si](C)(C)C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C	2845.3	Semi standard non polar	33892256
all-trans-18-Hydroxyretinoic acid,1TBDMS,isomer #1	CC(/C=C/C1=C(CO[Si](C)(C)C(C)(C)C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O	3092.7	Semi standard non polar	33892256
all-trans-18-Hydroxyretinoic acid,1TBDMS,isomer #2	CC(/C=C/C1=C(CO)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C	3057.1	Semi standard non polar	33892256
all-trans-18-Hydroxyretinoic acid,2TBDMS,isomer #1	CC(/C=C/C1=C(CO[Si](C)(C)C(C)(C)C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C	3282.0	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 - all-trans-18-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uds-1193000000-626f700ca215d387c08a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-18-Hydroxyretinoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-006t-7207900000-65114d88bd7672d578d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-18-Hydroxyretinoic acid 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 - all-trans-18-Hydroxyretinoic acid 10V, Positive-QTOF	splash10-0002-0291000000-333cc246ec7c4b1e0475	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 20V, Positive-QTOF	splash10-0k9b-1790000000-a89fdd69531c41151cfe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 40V, Positive-QTOF	splash10-000m-5900000000-9edad0e8ff3f631ee2cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 10V, Negative-QTOF	splash10-014i-0097000000-18d34b6fd796886621be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 20V, Negative-QTOF	splash10-014j-0092000000-92fbb8e3830fc0d48609	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 40V, Negative-QTOF	splash10-0670-1290000000-b6dfa3839044995ad66b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 10V, Negative-QTOF	splash10-014i-0097000000-b61c2e80fa56e367a872	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 20V, Negative-QTOF	splash10-0g4i-0190000000-d269f050ce5c3390aa06	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 40V, Negative-QTOF	splash10-016r-4890000000-44334e23d3a0de779de8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 10V, Positive-QTOF	splash10-01bm-0291000000-27b81458a8ba96303e29	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 20V, Positive-QTOF	splash10-00yl-0290000000-ea8b6b5eb2c38cb4c7b9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-18-Hydroxyretinoic acid 40V, Positive-QTOF	splash10-0kvo-7900000000-eb24d930d5dbda34997c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

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

FDB029068

KNApSAcK ID

Not Available

Chemspider ID

5005673

KEGG Compound ID

C16679

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6506224

PDB ID

Not Available

ChEBI ID

80657

Food Biomarker Ontology

Not Available

VMH ID

CE2957

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 4A11

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:: CYP4A11
Uniprot ID:: Q02928
Molecular weight:: 59347.31

Reactions

all-trans-Retinoic acid + NADPH + Hydrogen Ion + Oxygen → all-trans-18-Hydroxyretinoic acid + NADP + Water	details

Enzyme Details

2. Cytochrome P450 4A22

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:: CYP4A22
Uniprot ID:: Q5TCH4
Molecular weight:: 59245.28

Reactions

all-trans-Retinoic acid + NADPH + Hydrogen Ion + Oxygen → all-trans-18-Hydroxyretinoic acid + NADP + Water	details

Showing metabocard for all-trans-18-Hydroxyretinoic acid (HMDB0012452)

MOL for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

3D MOL for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

3D SDF for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

3D-SDF for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

PDB for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

3D PDB for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

SMILES for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

INCHI for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

Structure for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

3D Structure for HMDB0012452 (all-trans-18-Hydroxyretinoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions