MiMeDB: Showing metabocard for Nonanoylcarnitine (MMDBc0033542)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:53 UTC

Update Date

2024-04-30 20:12:17 UTC

Metabolite ID

MMDBc0033542

Metabolite Identification

Common Name

Nonanoylcarnitine

Description

Nonanoylcarnitine is an acylcarnitine. More specifically, it is an nonanoic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Nonanoylcarnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine nonanoylcarnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494 ). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. It is also decreased in the blood or plasma of individuals with psoriasis (PMID: 28695330 , PMID: 33391503 ), pregnancy (PMID: 24704061 - in serum of pregnant women with fetus with CHD). It is also decreased in the urine of individuals with obesity (PMID: 26910390 ). Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].

Structure

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

HMDB0013288
     RDKit          3D
Nonanoylcarnitine
 52 51  0  0  0  0  0  0  0  0999 V2000
    6.7652    1.4174    0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -0.0390    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1856   -0.4164   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8085    0.0620   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613   -0.4502   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.0109   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9177   -0.4396   -1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -0.0106   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -0.5321   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.2868   -0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.1533   -1.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -0.7012   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895   -1.5025   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -2.2903   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8688   -2.5357    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -2.8186   -1.7682 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.4358    0.5615   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4303    0.6383    0.9343 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7953    0.4632    0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3983    2.1099    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -0.0202    2.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431    2.0199    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.6955    1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    1.7079    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -0.5085    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0166   -0.4930    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -1.5198   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9397   -0.0332   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -0.3913   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326    1.1419   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.1364    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652   -1.5482   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4035    1.1442   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -0.2797    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.5636   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.0941   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.0978   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343   -0.3783   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908   -1.3125    0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370   -2.2333   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1132   -0.8611   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    1.2533    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272    1.1101   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9295    0.3137   -0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4555    1.3523    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3125   -0.3770    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774    2.2403    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    2.2648    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    2.6721    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5931    0.6654    3.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046   -0.0565    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.9592    2.3573 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  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 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
 12 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  CHG  2  16  -1  18   1
M  END


  Mrv1652301312018062D          

 21 20  0  0  0  0            999 V2000
    4.2355   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513   -4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -1.6204    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.3802   -1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802   -4.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -4.5079    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.6822   -5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8092   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  CHG  2  15  -1  18   1
M  END
> <DATABASE_ID>
MMDBc0033542

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H31NO4/c1-5-6-7-8-9-10-11-16(20)21-14(12-15(18)19)13-17(2,3)4/h14H,5-13H2,1-4H3

> <INCHI_KEY>
MPSPNFAQQQMFLK-UHFFFAOYSA-N

> <FORMULA>
C16H31NO4

> <MOLECULAR_WEIGHT>
301.4216

> <EXACT_MASS>
301.225308485

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22447157442417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(nonanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
-1.07843280080508

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.216763902737658

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057186892022333

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
104.8697

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(nonanoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013288
     RDKit          3D
Nonanoylcarnitine
 52 51  0  0  0  0  0  0  0  0999 V2000
    6.7652    1.4174    0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -0.0390    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1856   -0.4164   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8085    0.0620   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613   -0.4502   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.0109   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9177   -0.4396   -1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -0.0106   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -0.5321   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.2868   -0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.1533   -1.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -0.7012   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895   -1.5025   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -2.2903   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8688   -2.5357    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -2.8186   -1.7682 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.4358    0.5615   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4303    0.6383    0.9343 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7953    0.4632    0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3983    2.1099    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -0.0202    2.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431    2.0199    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.6955    1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    1.7079    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -0.5085    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0166   -0.4930    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -1.5198   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9397   -0.0332   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -0.3913   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326    1.1419   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.1364    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652   -1.5482   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4035    1.1442   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -0.2797    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.5636   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.0941   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.0978   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343   -0.3783   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908   -1.3125    0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370   -2.2333   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1132   -0.8611   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    1.2533    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272    1.1101   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9295    0.3137   -0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4555    1.3523    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3125   -0.3770    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774    2.2403    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    2.2648    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    2.6721    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5931    0.6654    3.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046   -0.0565    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.9592    2.3573 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  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 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
 12 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  CHG  2  16  -1  18   1
M  END

HEADER    PROTEIN                                 31-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JAN-20         0                                  
HETATM    1  C   UNK     0       7.906  -6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240  -5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.574  -6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.907  -5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.241  -6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.575  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.908  -6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.242  -5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.576  -6.105   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.576  -7.645   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      19.909  -5.335   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      21.243  -6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.577  -5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.577  -3.795   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      23.911  -3.025   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      21.243  -3.025   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      21.243  -7.645   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      22.577  -8.415   0.000  0.00  0.00           N+1
HETATM   19  C   UNK     0      21.807  -9.748   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.347  -7.081   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.911  -9.185   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0013288
HETATM    1  C1  UNL     1       6.765   1.417   0.953  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.674  -0.039   0.669  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.186  -0.416  -0.685  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.808   0.062  -1.030  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.761  -0.450  -0.093  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.361   0.011  -0.417  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.918  -0.440  -1.781  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.529  -0.011  -2.156  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.529  -0.532  -1.257  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.239  -1.287  -0.324  1.00  0.00           O  
HETATM   11  O2  UNL     1      -1.826  -0.153  -1.489  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.843  -0.701  -0.547  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.690  -1.503  -1.504  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.779  -2.290  -0.955  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.869  -2.536   0.252  1.00  0.00           O  
HETATM   16  O4  UNL     1      -5.793  -2.819  -1.768  1.00  0.00           O1-
HETATM   17  C13 UNL     1      -3.436   0.562  -0.042  1.00  0.00           C  
HETATM   18  N1  UNL     1      -4.430   0.638   0.934  1.00  0.00           N1+
HETATM   19  C14 UNL     1      -5.795   0.463   0.520  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.398   2.110   1.331  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.209  -0.020   2.181  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.343   2.020   0.120  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.340   1.696   1.945  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.843   1.708   1.005  1.00  0.00           H  
HETATM   25  H4  UNL     1       7.673  -0.508   0.874  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.017  -0.493   1.471  1.00  0.00           H  
HETATM   27  H6  UNL     1       6.233  -1.520  -0.772  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.940  -0.033  -1.429  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.581  -0.391  -2.042  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.733   1.142  -1.168  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.972  -0.136   0.965  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.765  -1.548  -0.092  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.403   1.144  -0.420  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.659  -0.280   0.377  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.941  -1.564  -1.859  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.656  -0.094  -2.541  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.489   1.098  -2.226  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.334  -0.378  -3.201  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.291  -1.312   0.148  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.037  -2.233  -2.083  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.113  -0.861  -2.314  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.562   1.253   0.243  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.827   1.110  -0.966  1.00  0.00           H  
HETATM   44  H23 UNL     1      -5.929   0.314  -0.565  1.00  0.00           H  
HETATM   45  H24 UNL     1      -6.455   1.352   0.756  1.00  0.00           H  
HETATM   46  H25 UNL     1      -6.312  -0.377   1.041  1.00  0.00           H  
HETATM   47  H26 UNL     1      -5.277   2.240   1.960  1.00  0.00           H  
HETATM   48  H27 UNL     1      -3.469   2.265   1.914  1.00  0.00           H  
HETATM   49  H28 UNL     1      -4.393   2.672   0.380  1.00  0.00           H  
HETATM   50  H29 UNL     1      -4.593   0.665   3.002  1.00  0.00           H  
HETATM   51  H30 UNL     1      -3.105  -0.056   2.402  1.00  0.00           H  
HETATM   52  H31 UNL     1      -4.724  -0.959   2.357  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   10   11
CONECT   11   12
CONECT   12   13   17   39
CONECT   13   14   40   41
CONECT   14   15   15   16
CONECT   17   18   42   43
CONECT   18   19   20   21
CONECT   19   44   45   46
CONECT   20   47   48   49
CONECT   21   50   51   52
END

HMDB0013288
     RDKit          3D
Nonanoylcarnitine
 52 51  0  0  0  0  0  0  0  0999 V2000
    6.7652    1.4174    0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6745   -0.0390    0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1856   -0.4164   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8085    0.0620   -1.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7613   -0.4502   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3613    0.0109   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9177   -0.4396   -1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292   -0.0106   -2.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286   -0.5321   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395   -1.2868   -0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.1533   -1.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -0.7012   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895   -1.5025   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7786   -2.2903   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8688   -2.5357    0.2524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -2.8186   -1.7682 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.4358    0.5615   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4303    0.6383    0.9343 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.7953    0.4632    0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3983    2.1099    1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -0.0202    2.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3431    2.0199    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.6955    1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8433    1.7079    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -0.5085    0.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0166   -0.4930    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2327   -1.5198   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9397   -0.0332   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -0.3913   -2.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326    1.1419   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -0.1364    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652   -1.5482   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4035    1.1442   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -0.2797    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.5636   -1.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.0941   -2.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4890    1.0978   -2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343   -0.3783   -3.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908   -1.3125    0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0370   -2.2333   -2.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1132   -0.8611   -2.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    1.2533    0.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8272    1.1101   -0.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9295    0.3137   -0.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4555    1.3523    0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3125   -0.3770    1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2774    2.2403    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4691    2.2648    1.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    2.6721    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5931    0.6654    3.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046   -0.0565    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241   -0.9592    2.3573 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  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 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
 12 39  1  0
 13 40  1  0
 13 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  CHG  2  16  -1  18   1
M  END

Synonyms

Value	Source
3-(Nonanoyloxy)-4-(trimethylammonio)butanoate	ChEBI
3-(Nonanoyloxy)-4-(trimethylammonio)butanoic acid	Generator
Nonayl-L-carnitine	HMDB
Nonaylcarnitine	HMDB

Molecular Formula

C₁₆H₃₁NO₄

Average Mass

301.4216

Monoisotopic Mass

301.225308485

IUPAC Name

3-(nonanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

3-(nonanoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

1935-18-8

SMILES

CCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C16H31NO4/c1-5-6-7-8-9-10-11-16(20)21-14(12-15(18)19)13-17(2,3)4/h14H,5-13H2,1-4H3

InChI Key

MPSPNFAQQQMFLK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

C9-acylcarnitine (CHEBI:70997 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00033 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.1	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.22	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	104.87 m³·mol⁻¹	ChemAxon
Polarizability	35.22 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Obesity	Decreased	Association	Human Urine	HMDB	26910390
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity		Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	153.82	7.30			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	HMDB	26910390
Human Blood	Detected and Quantified	0.059	0.017			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	0.03	0.01			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Urine	Detected and Quantified			0.03	0.18	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	32340350
Human Blood	Detected and Quantified	0.08	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	28278231
Human Urine	Detected and Quantified	0.08		0.04	0.19	umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.1		0.03	0.15	umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	HMDB	32340350
Human Urine	Detected and Quantified	0.20		0.07	0.46	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Feces	Detected and Quantified	0.6	0.32			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Urine	Detected and Quantified	225.05	13.63			umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	HMDB	26910390
Human Feces	Detected and Quantified	3.71	3.61			nmol/g wet feces	Adult (>18 years old)	Both	Normal	HMDB	27624970
Human Blood	Detected and Quantified	0.030	0.009			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.033	0.012			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified			0.020	0.100	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)

External Links

HMDB ID

HMDB0013288

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029365

KNApSAcK ID

Not Available

Chemspider ID

28533402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481699

PDB ID

Not Available

ChEBI ID

70997

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ferdinandusse S, Mulders J, IJlst L, Denis S, Dacremont G, Waterham HR, Wanders RJ: Molecular cloning and expression of human carnitine octanoyltransferase: evidence for its role in the peroxisomal beta-oxidation of branched-chain fatty acids. Biochem Biophys Res Commun. 1999 Sep 16;263(1):213-8. doi: 10.1006/bbrc.1999.1340. [PubMed:10486279 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ]
Ottas A, Fishman D, Okas TL, Kingo K, Soomets U: The metabolic analysis of psoriasis identifies the associated metabolites while providing computational models for the monitoring of the disease. Arch Dermatol Res. 2017 Sep;309(7):519-528. doi: 10.1007/s00403-017-1760-1. Epub 2017 Jul 10. [PubMed:28695330 ]
Violante S, Achetib N, van Roermund CWT, Hagen J, Dodatko T, Vaz FM, Waterham HR, Chen H, Baes M, Yu C, Argmann CA, Houten SM: Peroxisomes can oxidize medium- and long-chain fatty acids through a pathway involving ABCD3 and HSD17B4. FASEB J. 2019 Mar;33(3):4355-4364. doi: 10.1096/fj.201801498R. Epub 2018 Dec 12. [PubMed:30540494 ]
Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Nonanoylcarnitine (MMDBc0033542)

MOL for #<Metabolite:0x00007f9222eced28>

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