Arachidonic Acid

Details

• Internal ID: 28547294-72d5-404e-8891-7a0faec295e1
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
• SMILES (Canonical): CCCCCC=CCC=CCC=CCC=CCCCC(=O)O
• SMILES (Isomeric): CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
• InChI: InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
• InChI Key: YZXBAPSDXZZRGB-DOFZRALJSA-N
• Popularity: 52,108 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.50 g/mol
• Exact Mass: 304.240230259 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 6.22
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 14

Synonyms

• 506-32-1
• arachidonate
• Immunocytophyte
• (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
• (all-Z)-5,8,11,14-Eicosatetraenoic acid
• cis-5,8,11,14-Eicosatetraenoic acid
• 5,8,11,14-Eicosatetraenoic acid, (all-Z)-
• all-cis-5,8,11,14-eicosatetraenoic acid
• Arachidonsaeure
• 5Z,8Z,11Z,14Z-eicosatetraenoic acid
• (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid
• UNII-27YG812J1I
• CCRIS 6312
• CHEBI:15843
• 27YG812J1I
• (14C)Arachidonic acid
• EINECS 208-033-4
• CHEMBL15594
• AI3-09613
• DTXSID4040420
• Icosa-5,8,11,14-tetraenoic acid
• (5Z,8Z,11Z,14Z)-5,8,11,14-Eikosatetraensaeure
• 5Z,8Z,11Z,14Z-icosatetraenoic acid
• FA 20:4
• ARACHIDONIC ACID (20:4, n-6)
• (5Z,8Z,11Z,14Z)-Icosatetraenoic acid
• 5,8,11,14-Eicosatetraenoic acid
• C20:4
• cis-Delta(5,8,11,14)-eicosatetraenoic acid
• [1-14C]Arachidonic acid
• (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid
• ARACHIDONIC ACID (MART.)
• ARACHIDONIC ACID [MART.]
• 5,8,11,14-Eicosatetraenoic acid, labeled with carbon-14, (all-Z)-
• 93444-49-6
• Arachidonic Acid, 99%
• Icosa- 5, 8, 11, 14- tetraenoic acid
• Arachidonicacid
• Immunocytophyt
• Vevodar
• arachidonic-acid
• 1adl
• 1gnj
• 1vyg
• MFCD00004417
• (14C)-arachidonic acid
• Spectrum5_001910
• Arachidonic Acid, >97%
• D0HD9P
• Fatty Acid 20:4 n-6
• SCHEMBL16162
• BSPBio_001539
• MLS001361328
• ARACHIDONIC ACID [MI]
• AA-[d8]
• BML3-B03
• GTPL2391
• ARACHIDONIC ACID [INCI]
• 5,8,11,14-Eicosatetraenoate
• DTXCID2020420
• BDBM22319
• ARACHIDONIC ACID [WHO-DD]
• CHEBI:137828
• HMS1361M21
• HMS1791M21
• HMS1989M21
• HMS3402M21
• HMS3649B05
• 5Z,8Z,11Z,14Z-Eicosatetraenoate
• Arachidonic acid, >95.0% (GC)
• Arachidonic acid, analytical standard
• cis-D5,8,11,14-Eicosatetraenoate
• LMFA01030001
• s6185
• AKOS015950830
• CCG-214838
• DB04557
• FS-5880
• 5,8,11,14-all-cis-Eicosatetraenoate
• all-cis-5,8,11,14-Eicosatetraenoate
• ARACHIDONIC ACID (20:4 n-6)
• IDI1_034009
• cis-D5,8,11,14-Eicosatetraenoic acid
• NCGC00094608-01
• NCGC00094608-02
• NCGC00094608-03
• NCGC00094608-04
• NCGC00094608-05
• NCGC00094608-06
• (all-Z)-5,8,11,14-Eicosatetraenoate
• AC-14348
• AC-33769
• BP-29803
• SMR000857374
• 5,8,11,14-all-cis-Eicosatetraenoic acid
• All-cis-icosa-5,8,11,14-tetraenoic acid
• HY-109590
• A0781
• all-cis-eicosa-5,8,11,14-tetraenoic acid
• CS-0032762
• 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate
• Arachidonic acid (in Tocrisolvetrade mark100)
• C00219
• W15452
• FA(20:4(5Z,8Z,11Z,14Z))
• 5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid
• A929392
• Q407699
• SR-01000838311
• SR-01000838311-2
• BRD-K03070961-001-02-8
• BRD-K03070961-001-04-4
• (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoicacid
• (5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid #
• Arachidonic acid, from non-animal source, >=98.5% (GC)
• Arachidonic acid, from porcine liver, >=99% (GC), liquid
• D18DBC10-379C-4E78-9A50-8B791A2F4E68
• Arachidonic acid, from porcine liver, >=85% (capillary GC), liquid
• Arachidonic acid, 1.0 mg/mL in ethanol, certified reference material
• Arachidonic acid, from porcine liver, BioReagent, suitable for cell culture, >=99% (GC)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.5561	55.61%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Plasma membrane	0.5465	54.65%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6943	69.43%
P-glycoprotein inhibitior	-	0.6917	69.17%
P-glycoprotein substrate	-	0.9609	96.09%
CYP3A4 substrate	-	0.6718	67.18%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.9467	94.67%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8993	89.93%
CYP inhibitory promiscuity	-	0.9349	93.49%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7035	70.35%
Carcinogenicity (trinary)	Non-required	0.7021	70.21%
Eye corrosion	+	0.9611	96.11%
Eye irritation	+	0.6907	69.07%
Skin irritation	+	0.8622	86.22%
Skin corrosion	+	0.6450	64.50%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4166	41.66%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6301	63.01%
skin sensitisation	+	0.8676	86.76%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	-	0.7866	78.66%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7683	76.83%
Acute Oral Toxicity (c)	IV	0.8289	82.89%
Estrogen receptor binding	+	0.6731	67.31%
Androgen receptor binding	-	0.8729	87.29%
Thyroid receptor binding	+	0.6278	62.78%
Glucocorticoid receptor binding	+	0.6112	61.12%
Aromatase binding	-	0.6084	60.84%
PPAR gamma	+	0.8968	89.68%
Honey bee toxicity	-	0.9963	99.63%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9649	96.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	19952.6 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	2818.4 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	79.4 nM; 316.2 nM; 79.4 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	44668.4 nM; 2238.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	31622.8 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	31622.8 nM	Potency	via CMAUP
CHEMBL1978	P11511	Cytochrome P450 19A1	28200 nM	IC50	PMID: 16643058
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 39810.7 nM; 7943.3 nM; 39810.7 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	1995.3 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 12589.3 nM; 10000 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	1200 nM; 1200 nM	IC50; IC50	DOI: 10.1007/s00044-012-0285-6; DOI: 10.1007/s00044-008-9102-7
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	3100 nM	IC50	DOI: 10.1007/s00044-012-0285-6
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	1600 nM	IC50	DOI: 10.1007/s00044-012-0285-6
CHEMBL1293235	P02545	Prelamin-A/C	15848.9 nM	Potency	via CMAUP
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	602.56 nM	IC50	PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	1071.52 nM	IC50	PMID: 23571415
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	17782.8 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	3162.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	96.94%	99.17%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	93.41%	97.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.44%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	92.05%	89.63%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.97%	92.08%
CHEMBL221	P23219	Cyclooxygenase-1	91.59%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.87%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.54%	93.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	80.44%	85.94%

Plants that contains it

• Acanthosyris spinescens
• Agrimonia eupatoria
• Allium sativum
• Alluaudia humbertii
• Aloe
• Aloe vera
• Alstonia lanceolifera
• Brachystegia nigerica
• Campanula medium
• Cannabis sativa
• Cassia fistula
• Combretum indicum
• Curcuma longa
• Delphinium staphisagria
• Diplotaxis harra
• Dipteryx lacunifera
• Echinops spinosissimus
• Epilobium parviflorum
• Eruca vesicaria
• Euphorbia nivulia
• Fagopyrum esculentum
• Gleditsia triacanthos
• Gossypium hirsutum
• Hedlundia hybrida
• Hedwigia ciliata
• Hedyotis lawsoniae
• Hemionitis tenuifolia
• Humboldtia laurifolia
• Hyalosperma glutinosum
• Ilex macropoda
• Lycium cestroides
• Lycopodiella cernua
• Magnolia salicifolia
• Nigella sativa
• Onoclea struthiopteris
• Paepalanthus hilairei
• Phlebodium aureum
• Pieris formosa
• Populus balsamifera
• Portulaca oleracea
• Pterocaulon alopecuroides
• Rhabdodendron amazonicum
• Rhytidiadelphus squarrosus
• Rhytidiadelphus triquetrus
• Salvia fruticosa
• Selaginella uncinata
• Senna siamea
• Seriphidium caerulescens subsp. caerulescens
• Silybum marianum
• Sloanea zuliaensis
• Stellaria dichotoma
• Tetracera rosiflora
• Teucrium montanum
• Tillandsia fragrans
• Uvariopsis tripetala
• Zingiber zerumbet

Cross-Links

• PubChem: 444899
• NPASS: NPC91495
• ChEMBL: CHEMBL15594
• LOTUS: LTS0241153
• wikiData: Q407699