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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:36 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002100

Secondary Accession Numbers

HMDB02100

Metabolite Identification

Common Name

Palmitoylethanolamide

Description

N-Palmitoylethanolamide (PEA) is present in the tissues of most mammals. It was initially described as an agonist of the type 2 cannabinoid receptor (CB2), although it is now universally recognized that PEA is in fact incapable of binding to cannabinoid receptors, or at least not to the known receptors. In addition to its anti-inflammatory activity, PEA also produces analgesia, neuroprotection, and possesses anti-epileptic properties. It also reduces gastrointestinal motility and cancer cell proliferation, as well as protecting the vascular endothelium in the ischemic heart. The physiological stimuli that regulate PEA levels in mammalian tissues are largely unknown, however, multiple studies indicate that this lipid accumulates during cellular stress, particularly following tissue injury. For example, PEA increases post-mortem in the pig brain. Similar elevations in PEA levels have been observed in the ischemic brain and PEA is also up-regulated in response to ultraviolet-B irradiation in mouse epidermal cells. Adipose tissue is highly implicated in the systemic secretion of IL-6 and leptin, and human mature adipocytes are able to secrete large quantity of PEA. Human adipose tissue can be subjected to modulation of its inflammatory state by lipopolysaccharide (LPS). LPS strongly inhibits adipose cell leptin release, with PEA acting as a potentiator of this inhibitory effect. These actions are not linked to a reduction in leptin gene transcription. Thus, PEA does not have an anti-inflammatory role in the secretion of IL-6 via NFkappaB at the adipocyte level, but instead seems to act at the heart of the LPS-stimulated pathway, which, independently of NFkappaB, inhibits the secretion of leptin. (PMID: 16884908 ).

Structure

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

HMDB0002100
     RDKit          3D
Palmitoylethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.4733   -0.6253    1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606    0.7583    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754    1.1226    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    0.1467   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9897    0.5778   -1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.6744   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -0.5850   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236   -0.3656    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    0.0494   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427    0.2084    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    0.4546   -0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465    0.6114   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.6454   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.6736   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393   -1.7883   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -1.8393   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -2.7235   -0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -1.1054    0.7855 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.3117    1.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303    0.4401    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092    1.2535    0.4536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5619   -1.3464    0.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5094   -0.7030    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3711   -0.7902    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6807    1.5068    2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4720    0.8160    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.1996    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5762    2.1408   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.2821   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1634   -0.9007   -0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -0.1230   -2.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    1.5691   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394    1.0293   -1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6565    1.5036   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754   -1.3331   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -0.9469    0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.3940    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -1.3703    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288   -0.6247   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237    1.0907   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.7022    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.0332    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    1.3238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6910   -0.4674   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223    1.6720    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.0390    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430    0.6616   -0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    1.4833   -1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.6294   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312   -0.7446   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.7209   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468   -2.7738   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -1.7582    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.5004    2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4816   -0.8833    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9470    0.9737    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3827   -0.3529    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276    2.1049    0.7556 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
M  END


  Mrv0541 02231219222D          

 21 20  0  0  0  0            999 V2000
   30.0691   -5.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9270   -4.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7835   -3.9595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0676   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3532   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7821   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6387   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4966   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9241   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2111   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2097   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9256   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4952   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6400   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7808   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0662   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3546   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3517   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0691   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4980   -4.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2125   -3.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  2  0  0  0  0
  2 21  1  0  0  0  0
  3 19  1  0  0  0  0
  3 20  1  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  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002100

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)

> <INCHI_KEY>
HXYVTAGFYLMHSO-UHFFFAOYSA-N

> <FORMULA>
C18H37NO2

> <MOLECULAR_WEIGHT>
299.4919

> <EXACT_MASS>
299.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05062080252947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2-hydroxyethyl)hexadecanamide

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
4.983214217666667

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.451677713180988

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.463162762508802

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3259293688166086

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
90.09479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoylethanolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002100
     RDKit          3D
Palmitoylethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.4733   -0.6253    1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606    0.7583    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754    1.1226    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    0.1467   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9897    0.5778   -1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.6744   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -0.5850   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236   -0.3656    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    0.0494   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427    0.2084    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    0.4546   -0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465    0.6114   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.6454   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.6736   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393   -1.7883   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -1.8393   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -2.7235   -0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -1.1054    0.7855 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.3117    1.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303    0.4401    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092    1.2535    0.4536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5619   -1.3464    0.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5094   -0.7030    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3711   -0.7902    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6807    1.5068    2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4720    0.8160    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.1996    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5762    2.1408   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.2821   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1634   -0.9007   -0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -0.1230   -2.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    1.5691   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394    1.0293   -1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6565    1.5036   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754   -1.3331   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -0.9469    0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.3940    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -1.3703    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288   -0.6247   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237    1.0907   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.7022    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.0332    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    1.3238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6910   -0.4674   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223    1.6720    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.0390    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430    0.6616   -0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    1.4833   -1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.6294   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312   -0.7446   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.7209   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468   -2.7738   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -1.7582    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.5004    2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4816   -0.8833    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9470    0.9737    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3827   -0.3529    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276    2.1049    0.7556 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  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      56.129  -9.701   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      61.464  -8.161   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      57.463  -7.391   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      46.793  -7.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.459  -8.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      48.127  -8.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.126  -7.391   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.460  -7.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.792  -8.161   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      50.794  -8.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.458  -7.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.128  -7.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.124  -8.161   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.461  -8.161   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.791  -7.391   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.457  -8.161   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      54.795  -7.391   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.123  -7.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      56.129  -8.161   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      58.796  -8.161   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      60.130  -7.391   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   21                                                            
CONECT    3   19   20                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   17                                                       
CONECT   15   13   16                                                       
CONECT   16   15   18                                                       
CONECT   17   14   19                                                       
CONECT   18   16                                                            
CONECT   19    1    3   17                                                  
CONECT   20    3   21                                                       
CONECT   21    2   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0002100
HETATM    1  C1  UNL     1      -7.473  -0.625   1.861  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.561   0.758   1.247  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.375   1.123   0.411  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.165   0.147  -0.733  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.990   0.578  -1.576  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.681   0.674  -0.895  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.172  -0.585  -0.286  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.824  -0.366   0.358  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.785   0.049  -0.652  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.543   0.208   0.101  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.660   0.455  -0.900  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.946   0.611  -0.191  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.143   0.645  -1.141  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.148  -0.674  -1.927  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.239  -1.788  -0.924  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.565  -1.839  -0.243  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.354  -2.724  -0.800  1.00  0.00           O  
HETATM   18  N1  UNL     1       5.935  -1.105   0.785  1.00  0.00           N  
HETATM   19  C17 UNL     1       6.338  -0.312   1.898  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.630   0.440   1.527  1.00  0.00           C  
HETATM   21  O2  UNL     1       7.409   1.254   0.454  1.00  0.00           O  
HETATM   22  H1  UNL     1      -7.562  -1.346   1.000  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.509  -0.703   2.388  1.00  0.00           H  
HETATM   24  H3  UNL     1      -8.371  -0.790   2.520  1.00  0.00           H  
HETATM   25  H4  UNL     1      -7.681   1.507   2.090  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.472   0.816   0.583  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.480   1.200   1.069  1.00  0.00           H  
HETATM   28  H7  UNL     1      -6.576   2.141  -0.019  1.00  0.00           H  
HETATM   29  H8  UNL     1      -7.083   0.282  -1.385  1.00  0.00           H  
HETATM   30  H9  UNL     1      -6.163  -0.901  -0.443  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.908  -0.123  -2.442  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.247   1.569  -2.009  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.939   1.029  -1.671  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.656   1.504  -0.128  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.075  -1.333  -1.125  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.870  -0.947   0.497  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.884   0.394   1.139  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.506  -1.370   0.756  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.629  -0.625  -1.492  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.024   1.091  -1.002  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.669  -0.702   0.675  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.405   1.033   0.809  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.395   1.324  -1.549  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.691  -0.467  -1.537  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.922   1.672   0.234  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.062  -0.039   0.634  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.043   0.662  -0.532  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.139   1.483  -1.809  1.00  0.00           H  
HETATM   49  H28 UNL     1       5.113  -0.629  -2.517  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.331  -0.745  -2.621  1.00  0.00           H  
HETATM   51  H30 UNL     1       3.479  -1.721  -0.128  1.00  0.00           H  
HETATM   52  H31 UNL     1       4.047  -2.774  -1.447  1.00  0.00           H  
HETATM   53  H32 UNL     1       7.151  -1.758   0.893  1.00  0.00           H  
HETATM   54  H33 UNL     1       5.564   0.500   2.107  1.00  0.00           H  
HETATM   55  H34 UNL     1       6.482  -0.883   2.852  1.00  0.00           H  
HETATM   56  H35 UNL     1       7.947   0.974   2.438  1.00  0.00           H  
HETATM   57  H36 UNL     1       8.383  -0.353   1.205  1.00  0.00           H  
HETATM   58  H37 UNL     1       6.928   2.105   0.756  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   17   18
CONECT   18   19   53
CONECT   19   20   54   55
CONECT   20   21   56   57
CONECT   21   58
END

HMDB0002100
     RDKit          3D
Palmitoylethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -7.4733   -0.6253    1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5606    0.7583    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3754    1.1226    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    0.1467   -0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9897    0.5778   -1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814    0.6744   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -0.5850   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236   -0.3656    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847    0.0494   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427    0.2084    0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6598    0.4546   -0.8996 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9465    0.6114   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1427    0.6454   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483   -0.6736   -1.9273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393   -1.7883   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5647   -1.8393   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539   -2.7235   -0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -1.1054    0.7855 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3378   -0.3117    1.8980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303    0.4401    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092    1.2535    0.4536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5619   -1.3464    0.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5094   -0.7030    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3711   -0.7902    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6807    1.5068    2.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4720    0.8160    0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4799    1.1996    1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5762    2.1408   -0.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.2821   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1634   -0.9007   -0.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -0.1230   -2.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    1.5691   -2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394    1.0293   -1.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6565    1.5036   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0754   -1.3331   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8697   -0.9469    0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840    0.3940    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5060   -1.3703    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6288   -0.6247   -1.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0237    1.0907   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6688   -0.7022    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.0332    0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3951    1.3238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6910   -0.4674   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223    1.6720    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0617   -0.0390    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430    0.6616   -0.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1393    1.4833   -1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.6294   -2.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312   -0.7446   -2.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795   -1.7209   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0468   -2.7738   -1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513   -1.7582    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5639    0.5004    2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4816   -0.8833    2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9470    0.9737    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3827   -0.3529    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9276    2.1049    0.7556 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anandamide (16:0)	ChEBI
Hexadecanoyl ethanolamide	ChEBI
Hydroxyethylpalmitamide	ChEBI
Monoethanolamine palmitic acid amide	ChEBI
N-(2-Hydroxyethyl)palmitamide	ChEBI
N-Hexadecanoylethanolamine	ChEBI
N-Palmitoylethanolamine	ChEBI
Palmidrol	ChEBI
Palmidrolum	ChEBI
Palmitamide mea	ChEBI
Palmitic acid monoethanolamide	ChEBI
Palmitinsaeure-beta-hydroxyethylamid	ChEBI
Palmitoyl-ea	ChEBI
PEA	ChEBI
Palmdrol prodes	Kegg
Monoethanolamine palmitate amide	Generator
Palmitate monoethanolamide	Generator
Palmitinsaeure-b-hydroxyethylamid	Generator
Palmitinsaeure-β-hydroxyethylamid	Generator
Impulsin	MeSH
MimyX	MeSH
N-(2-Hydroxyethyl)palmitate	MeSH
Palmitylethanolamide	MeSH
N-Hexadecanoyl ethanolamine	ChEBI, HMDB
Loramine P 256	HMDB
N-(2-Hydroxyethyl)hexadecanamide	HMDB
N-Hexadecyl-ethanolamine	HMDB
Palmitoyl ethanolamide	HMDB
Palmitoylethanolamide	ChEBI

Chemical Formula

C₁₈H₃₇NO₂

Average Molecular Weight

299.4919

Monoisotopic Molecular Weight

299.282429433

IUPAC Name

N-(2-hydroxyethyl)hexadecanamide

Traditional Name

palmitoylethanolamide

CAS Registry Number

544-31-0

SMILES

CCCCCCCCCCCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h20H,2-17H2,1H3,(H,19,21)

InChI Key

HXYVTAGFYLMHSO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic acids

Alternative Parents

Substituents

Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-(long-chain-acyl)ethanolamine (CHEBI:71464 )
endocannabinoid (CHEBI:71464 )
N-(saturated fatty acyl)ethanolamine (CHEBI:71464 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040013 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0002100)

Biofluid or Excreta

Organ

Placenta (HMDB: HMDB0002100)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16115474)
Cerebrospinal Fluid (CSF) (PMID: 21177788)

Excreta

Biofluid or Excreta

Feces (PMID: 24628373)
Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0002100)
Membrane (HMDB: HMDB0002100)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002100)

Source

Endogenous

Endogenous (HMDB: HMDB0002100)

Plant

Plant (HMDB: HMDB0002100)
Fabaceae (HMDB: HMDB0002100)

Animal

Animal (HMDB: HMDB0002100)

Exogenous

Food

Food (HMDB: HMDB0002100)

Animal origin

Poultry

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Egg

Eggs (FooDB: FOOD00619)

Pulse

Pulses (FooDB: FOOD00867)

Nut

Nuts (FooDB: FOOD00869)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0002100)

Role

Biological role

Energy source (HMDB: HMDB0002100)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002100)

Emulsifier (HMDB: HMDB0002100)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	98.5 °C	Not Available
Boiling Point	461.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.44 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.820 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.74	ALOGPS
logP	4.98	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	15.46	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	90.09 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	0	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]+	178.526	31661259
DarkChem	[M-H]-	179.047	31661259
DeepCCS	[M+H]+	177.69	30932474
DeepCCS	[M-H]-	174.036	30932474
DeepCCS	[M-2H]-	210.819	30932474
DeepCCS	[M+Na]+	186.657	30932474
AllCCS	[M+H]+	183.3	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.6	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	183.7	32859911
AllCCS	[M+HCOO]-	185.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Palmitoylethanolamide	CCCCCCCCCCCCCCCC(=O)NCCO	3055.1	Standard polar	33892256
Palmitoylethanolamide	CCCCCCCCCCCCCCCC(=O)NCCO	2369.0	Standard non polar	33892256
Palmitoylethanolamide	CCCCCCCCCCCCCCCC(=O)NCCO	2542.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Palmitoylethanolamide,1TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)NCCO[Si](C)(C)C	2519.4	Semi standard non polar	33892256
Palmitoylethanolamide,1TMS,isomer #2	CCCCCCCCCCCCCCCC(=O)N(CCO)[Si](C)(C)C	2489.7	Semi standard non polar	33892256
Palmitoylethanolamide,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2596.4	Semi standard non polar	33892256
Palmitoylethanolamide,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2601.8	Standard non polar	33892256
Palmitoylethanolamide,2TMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2562.2	Standard polar	33892256
Palmitoylethanolamide,1TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	2736.2	Semi standard non polar	33892256
Palmitoylethanolamide,1TBDMS,isomer #2	CCCCCCCCCCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	2741.0	Semi standard non polar	33892256
Palmitoylethanolamide,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3046.9	Semi standard non polar	33892256
Palmitoylethanolamide,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2932.9	Standard non polar	33892256
Palmitoylethanolamide,2TBDMS,isomer #1	CCCCCCCCCCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2791.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-9550000000-2a81c82885f59140f22b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9342000000-ad8530134ab4732a0f8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoylethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylethanolamide 10V, Positive-QTOF	splash10-0udi-0198000000-1cff41413d7ea5aa691e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoylethanolamide 20V, Positive-QTOF	splash10-03e9-9150000000-f699f2ee45fd83d20176	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 10V, Positive-QTOF	splash10-0w29-7179000000-22766d934944105dccf9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 20V, Positive-QTOF	splash10-03dl-9130000000-c6d2bfc2e68da1f5b0d2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 40V, Positive-QTOF	splash10-01ox-9410000000-d078025cabaaf62c59b9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 10V, Negative-QTOF	splash10-0002-1090000000-5224a67dd0daaea79191	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 20V, Negative-QTOF	splash10-01ot-5090000000-dd9396934201d60f5af2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 40V, Negative-QTOF	splash10-0006-9010000000-d5bf936e945bfc965dfe	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 10V, Negative-QTOF	splash10-0002-0090000000-86444a8ba84f59241172	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 20V, Negative-QTOF	splash10-0002-3190000000-31bf9918e08d5134f37c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 40V, Negative-QTOF	splash10-052f-9120000000-95f7b48f422a8476addb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 10V, Positive-QTOF	splash10-0w29-9008000000-4fe7f397e16e4c5cdf0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-e26f03daa120b23660dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoylethanolamide 40V, Positive-QTOF	splash10-0006-9000000000-6cd5890dca5525a7b1e2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.013 (0.0094-0.0167) uM	Adult (>18 years old)	Both	Normal	16115474	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	25.1 +/- 12 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00212 +/- 0.00072 uM	Not Specified	Not Specified	normal	21177788	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001087

KNApSAcK ID

Not Available

Chemspider ID

4509

KEGG Compound ID

C16512

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Palmitoylethanolamide

METLIN ID

Not Available

PubChem Compound

4671

PDB ID

Not Available

ChEBI ID

71464

Food Biomarker Ontology

Not Available

VMH ID

PMETH

MarkerDB ID

Not Available

Good Scents ID

rw1301821

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hoareau L, Ravanan P, Gonthier MP, Delarue P, Goncalves J, Cesari M, Festy F, Roche R: Effect of PEA on LPS inflammatory action in human adipocytes. Cytokine. 2006 Jun;34(5-6):291-6. Epub 2006 Aug 1. [PubMed:16884908 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Palmitoylethanolamide (HMDB0002100)

MOL for HMDB0002100 (Palmitoylethanolamide)

3D MOL for HMDB0002100 (Palmitoylethanolamide)

3D SDF for HMDB0002100 (Palmitoylethanolamide)

3D-SDF for HMDB0002100 (Palmitoylethanolamide)

PDB for HMDB0002100 (Palmitoylethanolamide)

3D PDB for HMDB0002100 (Palmitoylethanolamide)

SMILES for HMDB0002100 (Palmitoylethanolamide)

INCHI for HMDB0002100 (Palmitoylethanolamide)

Structure for HMDB0002100 (Palmitoylethanolamide)

3D Structure for HMDB0002100 (Palmitoylethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra