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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-14 00:16:00 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004680

Secondary Accession Numbers

HMDB04680

Metabolite Identification

Common Name

16(R)-HETE

Description

16(R)-HETE is a metabolite of arachidonic acid, metabolized by the enzyme Cytochrome P450, family 2, subfamily C [EC:1.14.13.80 1.14.13.48 1.14.13.49]. 16(R)-HETE is an endogenous lipidic inhibitor of human neutrophil inhibitor of adhesion and aggregation activity. Human polymorphonuclear leukocytes (PMNs) produce 16(R)-HETE that modulates their function. HETEs have different biological properties based on sites of production and can be stored in tissue lipids and released in response to hormonal stimuli. Eicosanoids generated during the actions of growth factors and vasoconstrictors can modulate disease processes by affecting vascular homeostasis, inflammation, cellular growth, apoptosis and oxidant stress. In lung, the presence of these eicosanoids in the pulmonary vasculature and airways, including effects on pulmonary vascular and bronchial smooth muscle tone and airway epithelial ion transport. (PMID: 16258232 , 14626496 , 12681244 , 11123211 , 14552765 , 11126912 ).

Structure

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

HMDB0004680
     RDKit          3D
16(R)-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.7076    2.9431    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    1.9836    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    0.6035    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.4985    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955   -0.4647   -0.7876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1684    0.6690   -1.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218   -1.7413   -1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -2.0459   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -1.1100   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -0.7090   -1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -0.9381   -1.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -1.6091    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -2.8556   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -3.0503    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -2.0920    1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -1.7873    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605   -0.6181   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    0.6381    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488    1.6055    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5349    1.9657    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    2.6425   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    2.9700   -1.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107    2.9239   -1.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4097    3.9674    0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    2.8459    2.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6424    2.7158    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4318    2.2725   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6926    2.2247    1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055    0.5083    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0299    0.4449    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.4743    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6424   -1.4864    0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183   -0.4168   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    0.9535   -2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -2.5058   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -3.0007   -1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -0.2068   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -1.6663    0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785   -0.1899   -2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.6316   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -0.8577    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541   -1.6954    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9971   -3.6568   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -4.0468    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.6626    2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -1.2126    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526   -2.6495    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1038   -0.5237   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259    1.0892   -0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299    0.5197    0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161    2.5199    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4530    1.1081    1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.6318    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223    1.0099    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1456    3.6465   -1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END


  Mrv0541 02231219582D          

 23 22  0  0  1  0            999 V2000
   22.0450  -18.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3319  -16.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -18.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7594  -19.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4740  -19.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0450  -19.3458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1884  -19.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3305  -19.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9029  -19.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6160  -19.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1884  -17.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6160  -18.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4740  -16.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9029  -16.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4740  -16.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9015  -18.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0450  -16.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7594  -15.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6160  -16.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9015  -17.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3305  -15.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6160  -16.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -17.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  2 23  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 14 23  1  0  0  0  0
 15 18  2  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004680

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-/t19-/m1/s1

> <INCHI_KEY>
JEKNPVYFNMZRJG-STHMYGMFSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.4663

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.27809968707892

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z,16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.356359744

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.76794360696508

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819772010311794

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5881016361030094

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.4695

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16R-hete

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004680
     RDKit          3D
16(R)-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.7076    2.9431    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    1.9836    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    0.6035    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.4985    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955   -0.4647   -0.7876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1684    0.6690   -1.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218   -1.7413   -1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -2.0459   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -1.1100   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -0.7090   -1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -0.9381   -1.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -1.6091    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -2.8556   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -3.0503    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -2.0920    1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -1.7873    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605   -0.6181   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    0.6381    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488    1.6055    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5349    1.9657    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    2.6425   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    2.9700   -1.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107    2.9239   -1.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4097    3.9674    0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    2.8459    2.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6424    2.7158    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4318    2.2725   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6926    2.2247    1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055    0.5083    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0299    0.4449    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.4743    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6424   -1.4864    0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183   -0.4168   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    0.9535   -2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -2.5058   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -3.0007   -1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -0.2068   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -1.6663    0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785   -0.1899   -2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.6316   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -0.8577    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541   -1.6954    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9971   -3.6568   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -4.0468    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.6626    2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -1.2126    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526   -2.6495    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1038   -0.5237   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259    1.0892   -0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299    0.5197    0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161    2.5199    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4530    1.1081    1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.6318    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223    1.0099    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1456    3.6465   -1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      41.151 -34.572   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.153 -31.492   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.819 -33.802   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      42.484 -36.882   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.818 -36.112   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.151 -36.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      45.152 -36.882   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.817 -36.882   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.485 -36.112   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.483 -36.112   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.152 -32.262   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.483 -34.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.818 -31.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.485 -31.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      43.818 -29.952   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.149 -33.802   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.151 -29.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.484 -29.182   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.483 -31.492   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      37.149 -32.262   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.817 -29.182   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.483 -29.952   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      47.819 -32.262   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    1    4    8                                                  
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7                                                            
CONECT   10    8   12                                                       
CONECT   11   13   14                                                       
CONECT   12   10   16                                                       
CONECT   13   11   15                                                       
CONECT   14   11   23                                                       
CONECT   15   13   18                                                       
CONECT   16   12   20                                                       
CONECT   17   18   21                                                       
CONECT   18   15   17                                                       
CONECT   19   20   22                                                       
CONECT   20   16   19                                                       
CONECT   21   17   22                                                       
CONECT   22   19   21                                                       
CONECT   23    2    3   14                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0004680
HETATM    1  C1  UNL     1      -6.708   2.943   1.253  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.594   1.984   0.793  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.089   0.603   1.021  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.155  -0.498   0.667  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.795  -0.465  -0.788  1.00  0.00           C  
HETATM    6  O1  UNL     1      -4.168   0.669  -1.218  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.222  -1.741  -1.287  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.949  -2.046  -1.159  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.988  -1.110  -0.492  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.901  -0.709  -1.390  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.347  -0.938  -1.098  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.778  -1.609   0.145  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.499  -2.856  -0.089  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.714  -3.050   0.342  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.551  -2.092   1.112  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.791  -1.787   0.367  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.160  -0.618  -0.023  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.423   0.638   0.198  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.249   1.606   0.995  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.535   1.966   0.330  1.00  0.00           C  
HETATM   21  C20 UNL     1       6.364   2.642  -0.955  1.00  0.00           C  
HETATM   22  O2  UNL     1       5.249   2.970  -1.391  1.00  0.00           O  
HETATM   23  O3  UNL     1       7.511   2.924  -1.709  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.410   3.967   0.949  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.806   2.846   2.341  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.642   2.716   0.711  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.432   2.273  -0.266  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.693   2.225   1.357  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.306   0.508   2.115  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.030   0.445   0.448  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.291  -0.474   1.363  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.642  -1.486   0.865  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.818  -0.417  -1.311  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.413   0.953  -2.138  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.846  -2.506  -1.796  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.581  -3.001  -1.546  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.463  -0.207  -0.078  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.614  -1.666   0.383  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.178  -0.190  -2.353  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.141  -0.632  -1.787  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.545  -0.858   0.564  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.054  -1.695   0.949  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.997  -3.657  -0.648  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.182  -4.047   0.107  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.887  -2.663   2.057  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.075  -1.213   1.479  1.00  0.00           H  
HETATM   47  H24 UNL     1       5.453  -2.650   0.129  1.00  0.00           H  
HETATM   48  H25 UNL     1       6.104  -0.524  -0.577  1.00  0.00           H  
HETATM   49  H26 UNL     1       4.226   1.089  -0.822  1.00  0.00           H  
HETATM   50  H27 UNL     1       3.430   0.520   0.681  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.616   2.520   1.178  1.00  0.00           H  
HETATM   52  H29 UNL     1       5.453   1.108   1.984  1.00  0.00           H  
HETATM   53  H30 UNL     1       7.133   2.632   1.033  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.122   1.010   0.201  1.00  0.00           H  
HETATM   55  H32 UNL     1       8.146   3.646  -1.417  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6    7   33
CONECT    6   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   11   39
CONECT   11   12   40
CONECT   12   13   41   42
CONECT   13   14   14   43
CONECT   14   15   44
CONECT   15   16   45   46
CONECT   16   17   17   47
CONECT   17   18   48
CONECT   18   19   49   50
CONECT   19   20   51   52
CONECT   20   21   53   54
CONECT   21   22   22   23
CONECT   23   55
END

HMDB0004680
     RDKit          3D
16(R)-HETE
 55 54  0  0  0  0  0  0  0  0999 V2000
   -6.7076    2.9431    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5935    1.9836    0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0889    0.6035    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.4985    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7955   -0.4647   -0.7876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1684    0.6690   -1.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2218   -1.7413   -1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490   -2.0459   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878   -1.1100   -0.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -0.7090   -1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -0.9381   -1.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7781   -1.6091    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992   -2.8556   -0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7144   -3.0503    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -2.0920    1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -1.7873    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1605   -0.6181   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    0.6381    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2488    1.6055    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5349    1.9657    0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637    2.6425   -0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    2.9700   -1.3914 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107    2.9239   -1.7092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4097    3.9674    0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8063    2.8459    2.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6424    2.7158    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4318    2.2725   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6926    2.2247    1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3055    0.5083    2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0299    0.4449    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.4743    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6424   -1.4864    0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8183   -0.4168   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4134    0.9535   -2.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8458   -2.5058   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -3.0007   -1.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -0.2068   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -1.6663    0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1785   -0.1899   -2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -0.6316   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -0.8577    0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0541   -1.6954    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9971   -3.6568   -0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -4.0468    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8870   -2.6626    2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -1.2126    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526   -2.6495    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1038   -0.5237   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259    1.0892   -0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299    0.5197    0.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161    2.5199    1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4530    1.1081    1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1326    2.6318    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223    1.0099    0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1456    3.6465   -1.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoic acid	ChEBI
(5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoic acid	ChEBI
(all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid	ChEBI
(all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoic acid	ChEBI
16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoic acid	ChEBI
16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid	ChEBI
(16R,5Z,8Z,11Z,14Z)-16-Hydroxy-5,8,11,14-eicosatetraenoate	Generator
(5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate	Generator
(5Z,8Z,11Z,14Z)-(16R)-16-Hydroxyicosa-5,8,11,14-tetraenoate	Generator
(5Z,8Z,11Z,14Z,16R)-16-Hydroxyeicosa-5,8,11,14-tetraenoate	Generator
(all-cis)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate	Generator
(all-Z)-16(R)-Hydroxy-5,8,11,14-eicosatetraenoate	Generator
16(R)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoate	Generator
16(R)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoate	Generator
16-HETE	HMDB
16R-HETE	HMDB
16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoate	HMDB
16R-Hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid	HMDB

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(5Z,8Z,11Z,14Z,16R)-16-hydroxyicosa-5,8,11,14-tetraenoic acid

Traditional Name

16R-hete

CAS Registry Number

Not Available

SMILES

CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14-/t19-/m1/s1

InChI Key

JEKNPVYFNMZRJG-STHMYGMFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

16-HETE (CHEBI:34162 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C14778 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060069 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Extracellular (HMDB: HMDB0004680)
Membrane (HMDB: HMDB0004680)

Source

Exogenous

Exogenous (HMDB: HMDB0004680)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0004680)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Not Available

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	0.002 g/L	ALOGPS
logP	5.77	ALOGPS
logP	5.36	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.6	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	14	ChemAxon
Refractivity	101.47 m³·mol⁻¹	ChemAxon
Polarizability	37.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.946	31661259
DarkChem	[M-H]-	186.432	31661259
DeepCCS	[M+H]+	187.883	30932474
DeepCCS	[M-H]-	185.525	30932474
DeepCCS	[M-2H]-	218.411	30932474
DeepCCS	[M+Na]+	193.976	30932474
AllCCS	[M+H]+	186.9	32859911
AllCCS	[M+H-H2O]+	184.0	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.3	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	187.3	32859911
AllCCS	[M+HCOO]-	189.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.0 minutes	32390414
Predicted by Siyang on May 30, 2022	21.5711 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.94 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3108.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	395.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	285.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	643.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1039.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	571.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2069.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	711.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1782.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	728.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	363.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	487.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16(R)-HETE	CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	4011.1	Standard polar	33892256
16(R)-HETE	CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2313.9	Standard non polar	33892256
16(R)-HETE	CCCC[C@@H](O)\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O	2532.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16(R)-HETE,1TMS,isomer #1	CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C	2671.3	Semi standard non polar	33892256
16(R)-HETE,1TMS,isomer #2	CCCC[C@@H](O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C	2555.5	Semi standard non polar	33892256
16(R)-HETE,2TMS,isomer #1	CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2614.9	Semi standard non polar	33892256
16(R)-HETE,1TBDMS,isomer #1	CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C	2892.5	Semi standard non polar	33892256
16(R)-HETE,1TBDMS,isomer #2	CCCC[C@@H](O)/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C	2799.6	Semi standard non polar	33892256
16(R)-HETE,2TBDMS,isomer #1	CCCC[C@H](/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3113.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000277 +/- 0.000086 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023401

KNApSAcK ID

Not Available

Chemspider ID

7827807

KEGG Compound ID

C14778

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9548884

PDB ID

Not Available

ChEBI ID

34162

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

Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71. [PubMed:14626496 ]
Miyata N, Roman RJ: Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system. J Smooth Muscle Res. 2005 Aug;41(4):175-93. [PubMed:16258232 ]
Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10. [PubMed:11123211 ]
Natarajan R, Reddy MA: HETEs/EETs in renal glomerular and epithelial cell functions. Curr Opin Pharmacol. 2003 Apr;3(2):198-203. [PubMed:12681244 ]
Reddy YK, Reddy LM, Capdevila JH, Falck JR: Practical, asymmetric synthesis of 16-hydroxyeicosa-5(Z),8(Z), 11(Z),14(Z)-tetraenoic acid (16-HETE), an endogenous inhibitor of neutrophil activity. Bioorg Med Chem Lett. 2003 Nov 3;13(21):3719-20. [PubMed:14552765 ]
Bednar MM, Gross CE, Russell SR, Fuller SP, Ahern TP, Howard DB, Falck JR, Reddy KM, Balazy M: 16(R)-hydroxyeicosatetraenoic acid, a novel cytochrome P450 product of arachidonic acid, suppresses activation of human polymorphonuclear leukocyte and reduces intracranial pressure in a rabbit model of thromboembolic stroke. Neurosurgery. 2000 Dec;47(6):1410-8; discussion 1418-9. [PubMed:11126912 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

7. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8. Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9. Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Showing metabocard for 16(R)-HETE (HMDB0004680)

MOL for HMDB0004680 (16(R)-HETE)

3D MOL for HMDB0004680 (16(R)-HETE)

3D SDF for HMDB0004680 (16(R)-HETE)

3D-SDF for HMDB0004680 (16(R)-HETE)

PDB for HMDB0004680 (16(R)-HETE)

3D PDB for HMDB0004680 (16(R)-HETE)

SMILES for HMDB0004680 (16(R)-HETE)

INCHI for HMDB0004680 (16(R)-HETE)

Structure for HMDB0004680 (16(R)-HETE)

3D Structure for HMDB0004680 (16(R)-HETE)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes