Myristic acid

  • GreenMolBD CID : 707
  • Molecular Formula : C14H28O2
  • Molecular Weight : 228.376
  • Exact Molecular Mass : 228.209
  • IUPAC Name : tetradecanoic acid
  • 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)
  • InChI Key : TUNFSRHWOTWDNC-UHFFFAOYSA-N
  • Canonical SMILES : CCCCCCCCCCCCCC(=O)O
  • Isomeric SMILES : CCCCCCCCCCCCCC(=O)O
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

1.2. Taxonomy Tree

1.3. Alternative Parent

Straight chain fatty acids; Monocarboxylic acids and derivatives; Carboxylic acids; Organic oxides; Hydrocarbon derivatives; Carbonyl compounds;

1.4. Molecular Framework

Aliphatic acyclic compounds

1.5. Substituents

Long-chain 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

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
4.7721 37.3 1 2 16 12 0 0 6.87138 365.606 284.696 0.624651

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-206.823649 1.74 -5.177 -11.34714 0.99355 6.17

4. Compound Reactivity

DLP nRFG nLMR
3 0 1

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Non-Carcinogen Non-Mutagen Non-Toxic 5.97857 17288 0.916316 Moderate None None Degradable 0.000203121 4.65333

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes No Yes Yes Yes

7. Synonyms

Name
Tetradecanoic acid
MYRISTIC ACID
544-63-8
n-Tetradecanoic acid
n-Tetradecoic acid
Crodacid
n-Tetradecan-1-oic acid
1-Tridecanecarboxylic acid
Hydrofol acid 1495
Univol U 316S
Emery 655
Myristinsaeure
tetradecoic acid
Hystrene 9014
Neo-fat 14
Myristic acid (natural)
C14 fatty acid
Myristate
Myristic acid, pure
Tetradecanoate
acide tetradecanoique
NSC 5028
FEMA No. 2764
CCRIS 4724
CH3-[CH2]12-COOH
HSDB 5686
n-Myristic acid
C14:0
UNII-0I3V7S25AW
Philacid 1400
CHEBI:28875
AI3-15381
Prifac 2942
EINECS 208-875-2
1-tetradecanecarboxylic acid
BRN 0508624
CHEMBL111077
NSC5028
TUNFSRHWOTWDNC-UHFFFAOYSA-N
MFCD00002744
Lead dimyristate
ST023797
DSSTox_CID_1666
n-tetradecan-1-oate
DSSTox_RID_76274
DSSTox_GSID_21666
CAS-544-63-8
Myristic acid [NF]
myristoate
myristoic acid
n-Tetradecanoate
3usx
Myristic acid pure
n-Tetradecanoicacid
Myristic Acid Flake
Hystrene 9514
Kortacid 1499
Edenor C 14
Myristic Acid 655
1-Tridecanecarboxylate
Prifrac 2942
Myristic acid, 95%
Myristic acid, natural
tridecanecarboxylic acid
Myristic acid (8CI)
3v2n
3w9k
Myristic acid, puriss.
ACMC-1AKMJ
32112-52-0
Tetradecanoic acid (9CI)
bmse000737
D08OBF
Epitope ID:176772
C14:0 (Lipid numbers)
AC1L1WF8
AC1Q2W1A
SCHEMBL6374
4-02-00-01126 (Beilstein Handbook Reference)
KSC271K5J
MLS002152942
WLN: QV13
Tetradecanoic (Myristic) acid
0I3V7S25AW
AC1Q2W11
GTPL2806
DTXSID6021666
CTK1H1554
MolPort-001-779-744
s161
HMS3039E15
HMS3648O20
Myristic acid, analytical standard
tetradecanoic acid (myristic acid)
KS-00000JH9
NSC-5028
ZINC1530417
EINECS 250-924-5
Myristic acid, >=98.0% (GC)
Tox21_201852
Tox21_302781
ANW-32091
BDBM50147581
LMFA01010014
LS-210
SBB060024
Myristic acid, >=95%, FCC, FG
Myristic acid, Sigma Grade, >=99%
AKOS009156714
DB08231
MCULE-9671122893
NE10225
RTR-019260
NCGC00091068-01
NCGC00091068-02
NCGC00091068-03
NCGC00256547-01
NCGC00259401-01
AK114664
AN-21363
BT000309
LP003932
SMR001224536
AB1002562
KB-260944
TR-019260
FT-0602832
M0476
ST24025989
EN300-78099
C06424
Myristic acid, Vetec(TM) reagent grade, 98%
I04-0252
W-109088
F8889-5016
EDAE4876-C383-4AD4-A419-10C0550931DB
Myristic acid, pharmaceutical secondary standard
traceable to USP
Myristic acid, United States Pharmacopeia (USP) Reference Standard
45184-05-2
DS-3833
BG01529603
SR-01000854525
SR-01000854525-3
Certified Reference Material

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Myristic acid
Ammannia baccifera L. Aerial 1
Aquilaria malaccensis Wood 12
Areca catechu L. Nut 10 , 2 , 5 , 7 , 6 , 18
Artocarpus heterophyllus Lamk. Fruit 1
Coix lachryma Linn. Seed 8
Coriandrum sativum Linn. Seed; Stem 1 , 14 , 15 , 18 , 25 , 29
Cucurbita maxima Duchesne Seed 2
Cuscuta reflexa Leaf 1
Cyperus rotundus L 2 , 3
Echinochloa cruss-galli Root 4
Hygrophila auriculata Seed; Whole Part 1 , 2 , 6
Imperata cylindrica (L.)  Rhizome 8
Ipomoea batatas (L.) Lam. Root 4
Jatropha gossypifolia Seed 2 , 3 , 4
Juglans regia Fruit 4
Lantana camara L Leaf and Flower 3
Leucas aspera Leaf 1
Mangifera indica Fruit 7
Oryza sativa L. Seed 2
Rumex vesicarius Aerial 3
Tamarindus indica Fruit 8 , 9
Zanthoxylum rhetsa Bark 2

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
56 androgen receptor AR Homo sapiens 61.5015 743035
232 arachidonate 15-lipoxygenase, type B ALOX15B Homo sapiens 31.6228 881
41 chromobox 1 CBX1 Homo sapiens 89.1251 540317
112 Cyclooxygenase Bos taurus 1AL2,1AR6,1AR7,1AR8,1AR9,1ASJ,1AYM,1AYN,1BEV,1BJ5,1BKE,1CDK,1CMK,1COV,1CTP,1D4M,1DGI,1E7C,1E7G,1EAH,1EV1,1FK2,1H8T,1H9G,1H9Z,1HA2,1HBK,1HK4,1HK5,1HXS,1ICM,1IKU,1JSA,1L7Z,1LA3,1N5U,1NCR,1ND2,1NFP,1NN8, >500000 11421736
1139 Dynamin-1 Homo sapiens 1AL2,1AR6,1AR7,1AR8,1AR9,1ASJ,1AYM,1AYN,1BEV,1BJ5,1BKE,1CDK,1CMK,1COV,1CTP,1D4M,1DGI,1E7C,1E7G,1EAH,1EV1,1FK2,1H8T,1H9G,1H9Z,1HA2,1HBK,1HK4,1HK5,1HXS,1ICM,1IKU,1JSA,1L7Z,1LA3,1N5U,1NCR,1ND2,1NFP,1NN8, >100000 10.1016/j.bmcl.2004.03.096 15149689
57 estrogen receptor 1 ESR1 Homo sapiens 12.3013 743069
57 estrogen receptor 1 ESR1 Homo sapiens 21.8216 743069
57 estrogen receptor 1 ESR1 Homo sapiens 48.8524 743075
49 estrogen receptor 2 ESR2 Homo sapiens 60.9441 1259377
25 estrogen related receptor alpha ESRRA Homo sapiens 3.84531 1259403
256 flap structure-specific endonuclease 1 FEN1 Homo sapiens 100 588795
84 geminin, DNA replication inhibitor GMNN Homo sapiens 2.3109 624297
26 GLI family zinc finger 3 GLI3 Homo sapiens 24.3365 1259369
26 GLI family zinc finger 3 GLI3 Homo sapiens 22.9752 1259392
122 glucagon like peptide 1 receptor GLP1R Homo sapiens 14.1254 624417
58 heat shock protein family B (small) member 1 HSPB1 Homo sapiens 48.9722 743210
179 lysine acetyltransferase 2A KAT2A Homo sapiens 15.8489 504327
89 nuclear receptor subfamily 1 group H member 4 NR1H4 Homo sapiens 0.0032 588527
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 54.9477 720692
149 peroxisome proliferator activated receptor alpha PPARA Homo sapiens 5.4 1114584
149 peroxisome proliferator activated receptor alpha PPARA Homo sapiens 22.3872 651778
149 peroxisome proliferator activated receptor alpha PPARA Homo sapiens 44.6684 651778
53 peroxisome proliferator activated receptor delta PPARD Homo sapiens 24 1114582
53 peroxisome proliferator activated receptor delta PPARD Homo sapiens 51.874 743227
53 peroxisome proliferator activated receptor delta PPARD Homo sapiens 54.9477 743212
72 peroxisome proliferator activated receptor gamma PPARG Homo sapiens 12.3013 743191
72 peroxisome proliferator activated receptor gamma PPARG Homo sapiens 21 1114583
374 plasminogen Plg Mus musculus 12.5893 540303
375 plasminogen activator, urokinase Plau Mus musculus 12.5893 540303
376 plasminogen activator, urokinase receptor Plaur Mus musculus 12.5893 540303
285 polo like kinase 1 PLK1 Homo sapiens 29.9349 720504
150 Prostaglandin G/H synthase (cyclooxygenase) Ovis aries 1AL2,1AR6,1AR7,1AR8,1AR9,1ASJ,1AYM,1AYN,1BEV,1BJ5,1BKE,1CDK,1CMK,1COV,1CTP,1D4M,1DGI,1E7C,1E7G,1EAH,1EV1,1FK2,1H8T,1H9G,1H9Z,1HA2,1HBK,1HK4,1HK5,1HXS,1ICM,1IKU,1JSA,1L7Z,1LA3,1N5U,1NCR,1ND2,1NFP,1NN8, >500000 11421736
151 prostaglandin-endoperoxide synthase 1 PTGS1 Bos taurus 500 360928
152 prostaglandin-endoperoxide synthase 2 PTGS2 Ovis aries 500 360927
185 Rap guanine nucleotide exchange factor 3 RAPGEF3 Homo sapiens 56.2341 720707
51 retinoic acid receptor alpha RARA Homo sapiens 15.3085 1159552
54 retinoid X receptor alpha RXRA Homo sapiens 34.6697 1159527
54 retinoid X receptor alpha RXRA Homo sapiens 54.9477 1159531
678 sphingomyelin phosphodiesterase 1 SMPD1 Homo sapiens 223.872 504937
189 TAR DNA binding protein TARDBP Homo sapiens 0.7079 652104
47 thyroid hormone receptor beta Thrb Rattus norvegicus 27.2227 743065
47 thyroid hormone receptor beta Thrb Rattus norvegicus 57.711 743067
47 thyroid hormone receptor beta Thrb Rattus norvegicus 61.1306 743065
153 Toll-like receptor 2 Homo sapiens 1AL2,1AR6,1AR7,1AR8,1AR9,1ASJ,1AYM,1AYN,1BEV,1BJ5,1BKE,1CDK,1CMK,1COV,1CTP,1D4M,1DGI,1E7C,1E7G,1EAH,1EV1,1FK2,1H8T,1H9G,1H9Z,1HA2,1HBK,1HK4,1HK5,1HXS,1ICM,1IKU,1JSA,1L7Z,1LA3,1N5U,1NCR,1ND2,1NFP,1NN8, 5000 10.1021/jm050585d 16509590
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 5.8048 686978
126 ubiquitin specific peptidase 1 USP1 Homo sapiens 63.0957 743255
64 vitamin D receptor VDR Homo sapiens 19.9526 588543

10. Chemical Vendors

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172910700Nanjing KaimuboSource URLSource DetailKB-260944Source Record URL
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164788011Finetech Industry LimitedSource URLSource DetailFT-0602832Source Record URL
329749968Sigma-AldrichSource URLSource Detail130087_ALDRICHSource Record URL
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24896795Sigma-AldrichSource URLSource DetailM3128_SIGMASource Record URL
329823145Sigma-AldrichSource URLSource DetailPHR1124_SIALSource Record URL
329828756Sigma-AldrichSource URLSource DetailV001705_VETECSource Record URL
329829811Sigma-AldrichSource URLSource DetailV900402_VETECSource Record URL
24901313Sigma-AldrichSource URLSource DetailW276405_ALDRICHSource Record URL
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315369180Life ChemicalsSource URLSource DetailF8889-5016Source Record URL
342433001Wubei-BiochemSource URLSource DetailWB020595SUSource Record URL
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