tetradecanoic acid (CHEBI:28875)

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CHEBI:28875 - tetradecanoic acid

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ChEBI Name	tetradecanoic acid

ChEBI ID	CHEBI:28875

Definition	A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Johnny Lloyd

Secondary ChEBI IDs	CHEBI:278516, CHEBI:44232, CHEBI:73168, CHEBI:26897, CHEBI:7056

Supplier Information	ZINC000015149528

Download	Molfile XML SDF

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Molfile

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Mrv0541 02171517153D

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Mrv0541 02171517153D

44 43 0 0 0 0 999 V2000

7.1881 -2.8607 3.7686 C 0 0 0 0 0 0 0 0 0 0 0 0

7.3153 -4.0098 3.4105 O 0 0 0 0 0 0 0 0 0 0 0 0

7.6676 -1.8514 2.9916 O 0 0 0 0 0 0 0 0 0 0 0 0

6.4846 -2.5476 5.0697 C 0 0 2 0 0 0 0 0 0 0 0 0

4.9659 -2.6785 4.9013 C 0 0 2 0 0 0 0 0 0 0 0 0

4.4469 -1.5946 3.9520 C 0 0 2 0 0 0 0 0 0 0 0 0

2.9316 -1.7275 3.7868 C 0 0 2 0 0 0 0 0 0 0 0 0

2.4256 -0.5827 2.9071 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9071 -0.6800 2.7471 C 0 0 2 0 0 0 0 0 0 0 0 0

0.4181 0.5177 1.9317 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.1066 0.4653 1.7852 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.6059 1.7081 1.0392 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.3431 2.9628 1.8792 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.8185 4.2075 1.1261 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.5676 5.4448 1.9914 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.0289 6.6994 1.2466 C 0 0 0 0 0 0 0 0 0 0 0 0

8.1294 -2.0624 2.1162 H 0 0 0 0 0 0 0 0 0 0 0 0

6.7364 -1.5094 5.3748 H 0 0 0 0 0 0 0 0 0 0 0 0

6.8344 -3.2583 5.8487 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4747 -2.5648 5.8913 H 0 0 0 0 0 0 0 0 0 0 0 0

4.7270 -3.6789 4.4814 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9362 -1.7078 2.9609 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6846 -0.5934 4.3708 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4423 -1.6765 4.7829 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6931 -2.7003 3.3059 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9060 -0.6464 1.9075 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6843 0.3881 3.3815 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4251 -0.6714 3.7481 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6472 -1.6220 2.2185 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8863 0.4915 0.9245 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7063 1.4569 2.4505 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5717 0.4303 2.7935 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3898 -0.4448 1.2143 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6969 1.6121 0.8526 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0702 1.7956 0.0698 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2541 3.0496 2.0808 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.8932 2.8837 2.8413 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9048 4.1189 0.9104 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2573 4.3012 0.1719 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4821 5.5260 2.2132 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1345 5.3512 2.9423 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4572 6.4094 0.2633 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1615 7.3754 1.0878 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8032 7.2228 1.8477 H 0 0 0 0 0 0 0 0 0 0 0 0

15 16 1 0 0 0 0

14 15 1 0 0 0 0

13 14 1 0 0 0 0

12 13 1 0 0 0 0

11 12 1 0 0 0 0

10 11 1 0 0 0 0

9 10 1 0 0 0 0

8 9 1 0 0 0 0

7 8 1 0 0 0 0

6 7 1 0 0 0 0

5 6 1 0 0 0 0

4 5 1 0 0 0 0

1 4 1 0 0 0 0

1 3 1 0 0 0 0

1 2 2 0 0 0 0

17 3 1 0 0 0 0

18 4 1 0 0 0 0

19 4 1 0 0 0 0

20 5 1 0 0 0 0

21 5 1 0 0 0 0

22 6 1 0 0 0 0

23 6 1 0 0 0 0

24 7 1 0 0 0 0

25 7 1 0 0 0 0

26 8 1 0 0 0 0

27 8 1 0 0 0 0

28 9 1 0 0 0 0

29 9 1 0 0 0 0

30 10 1 0 0 0 0

31 10 1 0 0 0 0

32 11 1 0 0 0 0

33 11 1 0 0 0 0

34 12 1 0 0 0 0

35 12 1 0 0 0 0

36 13 1 0 0 0 0

37 13 1 0 0 0 0

38 14 1 0 0 0 0

39 14 1 0 0 0 0

40 15 1 0 0 0 0

41 15 1 0 0 0 0

42 16 1 0 0 0 0

43 16 1 0 0 0 0

44 16 1 0 0 0 0

M END): 18 ms

reading 44 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

44 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
[object Object]
Read full article at Wikipedia

Formula

C14H28O2

Net Charge

Average Mass

228.37090

Monoisotopic Mass

228.20893

InChI

InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

InChIKey

TUNFSRHWOTWDNC-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCCCC(O)=O

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Daphnia magna (NCBI:txid35525)	See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Homo sapiens (NCBI:txid9606)	Found in blood serum (BTO:0000133). See: MetaboLights Study

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Daphnia magna metabolite A Daphnia metabolite produced by the species Daphnia magna. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. EC 3.1.1.1 (carboxylesterase) inhibitor Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	tetradecanoic acid (CHEBI:28875) has role Daphnia magna metabolite (CHEBI:83056) tetradecanoic acid (CHEBI:28875) has role algal metabolite (CHEBI:84735) tetradecanoic acid (CHEBI:28875) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444) tetradecanoic acid (CHEBI:28875) has role human metabolite (CHEBI:77746) tetradecanoic acid (CHEBI:28875) is a long-chain fatty acid (CHEBI:15904) tetradecanoic acid (CHEBI:28875) is a straight-chain saturated fatty acid (CHEBI:39418) tetradecanoic acid (CHEBI:28875) is conjugate acid of tetradecanoate (CHEBI:30807)

Incoming	β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-tetradecanoylsphingosine (CHEBI:91034) has functional parent tetradecanoic acid (CHEBI:28875) (13R)-13-hydroxymyristic acid (CHEBI:78989) has functional parent tetradecanoic acid (CHEBI:28875) (R)-3-hydroxytetradecanoic acid (CHEBI:42539) has functional parent tetradecanoic acid (CHEBI:28875) (S)-3-hydroxytetradecanoic acid (CHEBI:37374) has functional parent tetradecanoic acid (CHEBI:28875) 1,2-ditetradecanoyl-3-(6-sulfoquinovopyranosyl)glycerol (CHEBI:134427) has functional parent tetradecanoic acid (CHEBI:28875) 1,2-ditetradecanoyl-sn-glycero-3-cytidine 5'-diphosphate (CHEBI:103211) has functional parent tetradecanoic acid (CHEBI:28875) 1,2-ditetradecanoyl-sn-glycerol (CHEBI:80651) has functional parent tetradecanoic acid (CHEBI:28875) 1-(1Z-hexadecenyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine (CHEBI:133669) has functional parent tetradecanoic acid (CHEBI:28875) 1-O-(α-D-galactopyranosyl)-N-tetradecanoylphytosphingosine (CHEBI:84158) has functional parent tetradecanoic acid (CHEBI:28875) 1-docosanoyl-2-tetradecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:134228) has functional parent tetradecanoic acid (CHEBI:28875) 1-icosanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine (CHEBI:134231) has functional parent tetradecanoic acid (CHEBI:28875) 1-naphthyl tetradecanoate (CHEBI:132330) has functional parent tetradecanoic acid (CHEBI:28875) 1-tetradecanoyl-2,3-dihexadecanoyl-sn-glycerol (CHEBI:108517) has functional parent tetradecanoic acid (CHEBI:28875) 1-tetradecanoyl-2-docosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:134077) has functional parent tetradecanoic acid (CHEBI:28875) 1-tetradecanoyl-2-icosanoyl-sn-glycero-3-phosphocholine (CHEBI:134218) has functional parent tetradecanoic acid (CHEBI:28875) 10-hydroxymyristic acid (CHEBI:167620) has functional parent tetradecanoic acid (CHEBI:28875) 10-methyltetradecanoic acid (CHEBI:132910) has functional parent tetradecanoic acid (CHEBI:28875) 11-hydroxymyristic acid (CHEBI:167619) has functional parent tetradecanoic acid (CHEBI:28875) 12-hydroxymyristic acid (CHEBI:167621) has functional parent tetradecanoic acid (CHEBI:28875) 13-hydroxytetradecanoic acid (CHEBI:132473) has functional parent tetradecanoic acid (CHEBI:28875) 14-hydroxymyristic acid (CHEBI:77168) has functional parent tetradecanoic acid (CHEBI:28875) 3-hydroxytetradecanoic acid (CHEBI:85148) has functional parent tetradecanoic acid (CHEBI:28875) 3-oxotetradecanoic acid (CHEBI:37270) has functional parent tetradecanoic acid (CHEBI:28875) 9-hydroxymyristic acid (CHEBI:167573) has functional parent tetradecanoic acid (CHEBI:28875) N,N-dimethyltetradecanamide (CHEBI:146190) has functional parent tetradecanoic acid (CHEBI:28875) N-(tetradecanoyl)ethanolamine (CHEBI:85262) has functional parent tetradecanoic acid (CHEBI:28875) N-myristoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85793) has functional parent tetradecanoic acid (CHEBI:28875) N-myristoylglycine (CHEBI:87142) has functional parent tetradecanoic acid (CHEBI:28875) N-myristoylsphingosine-1-phosphocholine (CHEBI:64486) has functional parent tetradecanoic acid (CHEBI:28875) N-tetradecanoyl-(2S)-hydroxyglycine (CHEBI:142741) has functional parent tetradecanoic acid (CHEBI:28875) N-tetradecanoylsphingosine (CHEBI:72957) has functional parent tetradecanoic acid (CHEBI:28875) N-tetradecanoylsphingosine 1-phosphate (CHEBI:73146) has functional parent tetradecanoic acid (CHEBI:28875) N-tetradecanoyltaurine (CHEBI:132476) has functional parent tetradecanoic acid (CHEBI:28875) S-tetradecanoyl-4ʼ-phosphopantetheine (CHEBI:132319) has functional parent tetradecanoic acid (CHEBI:28875) klymollin F (CHEBI:68956) has functional parent tetradecanoic acid (CHEBI:28875) methyl tetradecanoate (CHEBI:89199) has functional parent tetradecanoic acid (CHEBI:28875) monoacylglycerol 14:0 (CHEBI:87249) has functional parent tetradecanoic acid (CHEBI:28875) myristamide (CHEBI:137125) has functional parent tetradecanoic acid (CHEBI:28875) myristoyl-CoA (CHEBI:15532) has functional parent tetradecanoic acid (CHEBI:28875) tetradecanoate ester (CHEBI:87691) has functional parent tetradecanoic acid (CHEBI:28875) tetradecanoic-d₂₇ acid (CHEBI:134623) has functional parent tetradecanoic acid (CHEBI:28875) tetradecanoyl-AMP (CHEBI:84412) has functional parent tetradecanoic acid (CHEBI:28875) tetradecanoate (CHEBI:30807) is conjugate base of tetradecanoic acid (CHEBI:28875) tetradecanoyl group (CHEBI:25456) is substituent group from tetradecanoic acid (CHEBI:28875)

IUPAC Name

myristic acid

Synonyms	Sources
1-tetradecanecarboxylic acid	ChEBI
14	ChEBI
14:0	ChEBI
14:00	ChEBI
acide tétradécanoïque	ChEBI
C14	ChEBI
CH₃‒[CH₂]₁₂‒COOH	IUPAC
Myristic acid	KEGG COMPOUND
MYRISTIC ACID	PDBeChem
Myristic acid	KEGG COMPOUND
Myristinsäure	ChEBI
n-Tetradecan-1-oic acid	ChemIDplus
n-tetradecanoic acid	NIST Chemistry WebBook
n-Tetradecoic acid	ChemIDplus
Tetradecanoic acid	KEGG COMPOUND
tetradecoic acid	ChEBI

Manual Xrefs	Databases
C00001228	KNApSAcK
C06424	KEGG COMPOUND
CPD-7836	MetaCyc
DB08231	DrugBank
HMDB0000806	HMDB
LMFA01010014	LIPID MAPS
MYR	PDBeChem
Myristic_acid	Wikipedia
View more database links

Registry Numbers	Types	Sources
242115	Gmelin Registry Number	Gmelin
508624	Reaxys Registry Number	Reaxys
544-63-8	CAS Registry Number	KEGG COMPOUND
544-63-8	CAS Registry Number	ChemIDplus
544-63-8	CAS Registry Number	NIST Chemistry WebBook

Citations	Types	Sources
13129458	PubMed citation	Europe PMC
15149689	PubMed citation	ChEMBL
16509590	PubMed citation	ChEMBL
16554156	PubMed citation	ChEMBL
19154695	PubMed citation	Europe PMC
19761868	PubMed citation	Europe PMC
19786012	PubMed citation	Europe PMC
19902021	PubMed citation	Europe PMC
19955401	PubMed citation	Europe PMC
20634506	PubMed citation	Europe PMC
20920594	PubMed citation	Europe PMC
21955528	PubMed citation	Europe PMC
22030224	PubMed citation	Europe PMC
27206979	PubMed citation	Europe PMC
28600633	PubMed citation	Europe PMC
6802973	PubMed citation	ChEMBL

Last Modified

08 March 2021

General Comment
2010-04-22	Additional citation (no PMID) -- Kawahara K et al., (1994): Isolation of Sphingomonas Strains from Ears of Rice and Other Plants of Family Gramineae - Biosci. Biotech. Biochem. 58(3): 600-601.

CHEBI:28875 - tetradecanoic acid

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