MiMeDB: Showing metabocard for (7Z,10Z,13Z,16Z)-docosatetraenoate (MMDBc0000698)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:00 UTC

Update Date

2022-08-31 06:11:11 UTC

Metabolite ID

MMDBc0000698

Metabolite Identification

Common Name

(7Z,10Z,13Z,16Z)-docosatetraenoate

Description

Adrenic acid, also known as adrenate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Adrenic acid is a weakly acidic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920572D          

 24 23  0  0  0  0            999 V2000
   -6.0987    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9552    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9552   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2408   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  7  8  1  4  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 10 11  1  4  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 13 14  1  4  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 17  1  4  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000698

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)

> <INCHI_KEY>
TWSWSIQAPQLDBP-UHFFFAOYSA-N

> <FORMULA>
C22H36O2

> <MOLECULAR_WEIGHT>
332.52

> <EXACT_MASS>
332.271530396

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.58987076771654

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
docosa-7,10,13,16-tetraenoic acid

> <ALOGPS_LOGP>
7.42

> <JCHEM_LOGP>
7.4763081410000005

> <ALOGPS_LOGS>
-6.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.955292438746737

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
109.15599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
docosa-7,10,13,16-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0     -11.384   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.050   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.050   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.717   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.717   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.383   0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.383  -1.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.049  -1.953   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.716  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.382  -1.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.048  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.048   0.357   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.715   1.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.715   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.619   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+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                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
Adrenate	Generator
Adrenic acid, (Z)-isomer	MeSH

Molecular Formula

C₂₂H₃₆O₂

Average Mass

332.52

Monoisotopic Mass

332.271530396

IUPAC Name

docosa-7,10,13,16-tetraenoic acid

Traditional Name

docosa-7,10,13,16-tetraenoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O

InChI Identifier

InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)

InChI Key

TWSWSIQAPQLDBP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.8e-05 g/L	ALOGPS
logP	7.42	ALOGPS
logP	7.48	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	109.16 m³·mol⁻¹	ChemAxon
Polarizability	41.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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	Data Source	Reference
MMDBr0001119	(7Z,10Z,13Z,16Z)-docosatetraenoate	Adrenyl coenzyme A	Not Available	VMH	15292367
MMDBr0002031	Adrenyl coenzyme A	(7Z,10Z,13Z,16Z)-docosatetraenoate	acyl-CoA thioesterase 2	VMH	10944470
MMDBr0009294	Adrenyl coenzyme A	(7Z,10Z,13Z,16Z)-docosatetraenoate	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0010000	(7Z,10Z,13Z,16Z)-docosatetraenoate	Adrenyl coenzyme A	Not Available	VMH	30371894
MMDBr0010219	Cholest-5-En-3Beta-Yl (7Z,10Z,13Z,16Z-Docosatetraenoate)	(7Z,10Z,13Z,16Z)-docosatetraenoate	carboxyl ester lipase	VMH; KEGG	30371894
MMDBr0010256	Cholest-5-En-3Beta-Yl (7Z,10Z,13Z,16Z-Docosatetraenoate)	(7Z,10Z,13Z,16Z)-docosatetraenoate	carboxyl ester lipase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human appendix biopsy; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	2	Human ; Human feces; Human saliva; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189
Animal	Milk	Bos taurus	FooDB	M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022918

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Docosatetraenoic acid

METLIN ID

Not Available

PubChem Compound

2033

PDB ID

Not Available

ChEBI ID

131693

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jones JM, Gould SJ: Identification of PTE2, a human peroxisomal long-chain acyl-CoA thioesterase. Biochem Biophys Res Commun. 2000 Aug 18;275(1):233-40. doi: 10.1006/bbrc.2000.3285. [PubMed:10944470 ]
Mashek DG, Bornfeldt KE, Coleman RA, Berger J, Bernlohr DA, Black P, DiRusso CC, Farber SA, Guo W, Hashimoto N, Khodiyar V, Kuypers FA, Maltais LJ, Nebert DW, Renieri A, Schaffer JE, Stahl A, Watkins PA, Vasiliou V, Yamamoto TT: Revised nomenclature for the mammalian long-chain acyl-CoA synthetase gene family. J Lipid Res. 2004 Oct;45(10):1958-61. doi: 10.1194/jlr.E400002-JLR200. Epub 2004 Aug 1. [PubMed:15292367 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for (7Z,10Z,13Z,16Z)-docosatetraenoate (MMDBc0000698)

MOL for #<Metabolite:0x0000556b6ab22228>

3D MOL for #<Metabolite:0x0000556b6ab22228>

3D SDF for #<Metabolite:0x0000556b6ab22228>

3D-SDF for #<Metabolite:0x0000556b6ab22228>

PDB for #<Metabolite:0x0000556b6ab22228>

3D PDB for #<Metabolite:0x0000556b6ab22228>

SMILES for #<Metabolite:0x0000556b6ab22228>

INCHI for #<Metabolite:0x0000556b6ab22228>

Structure for #<Metabolite:0x0000556b6ab22228>

3D Structure for #<Metabolite:0x0000556b6ab22228>