5,8,11,14-Eicosatetraynoic acid

Details

• Internal ID: 83c01f4b-1dda-495d-bdbc-af0adef4d31e
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
• IUPAC Name: icosa-5,8,11,14-tetraynoic acid
• SMILES (Canonical): CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
• SMILES (Isomeric): CCCCCC#CCC#CCC#CCC#CCCCC(=O)O
• InChI: InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
• InChI Key: MGLDCXPLYOWQRP-UHFFFAOYSA-N
• Popularity: 934 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₂
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.177630004 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 5,8,11,14-eicosatetraynoic acid
• 1191-85-1
• Eicosatetraynoic acid
• icosa-5,8,11,14-tetraynoic acid
• eicosatetranoic acid
• Ro 3-1428
• Ro 31428
• 5FEJ8J06DR
• MLS000069514
• SMR000058640
• MLS-0002886.0001
• ITY
• MFCD00036967
• Opera_ID_402
• Spectrum5_001952
• D0G9IP
• UNII-5FEJ8J06DR
• cid_1780
• CBiol_001864
• SCHEMBL68751
• BSPBio_001449
• KBioGR_000169
• KBioSS_000169
• BML2-F04
• CHEMBL458328
• GTPL2669
• BDBM31752
• CHEBI:94483
• KBio2_000169
• KBio2_002737
• KBio2_005305
• KBio3_000337
• KBio3_000338
• DTXSID20152318
• MGLDCXPLYOWQRP-UHFFFAOYSA-N
• Bio1_000150
• Bio1_000639
• Bio1_001128
• Bio2_000169
• Bio2_000649
• HMS1361I11
• HMS1791I11
• HMS1989I11
• HMS3402I11
• HMS3649D21
• BAA19185
• HSCI1_000035
• LMFA01030691
• '5,8,11,14-eicosatetraynoic acid'
• 5,8,11,14-Icosatetraynoic acid #
• AKOS040733080
• 'icosa-5,8,11,14-tetraynoic acid'
• CCG-207933
• IDI1_033919
• NCGC00018135-01
• NCGC00018135-02
• NCGC00018135-03
• NCGC00018135-04
• NCGC00018135-05
• NCGC00018135-06
• NCGC00021784-03
• NCGC00021784-04
• NCGC00021784-05
• ETYA - CAS 1191-85-1
• MS-24251
• HY-124108
• CS-0084220
• EICOSA-5,8,11,14-TETRAYNOIC ACID
• 5,8,11,14-Eicosatetraynoic acid, >=97%
• SR-01000000036
• J-004079
• SR-01000000036-3
• SR-01000000036-4
• Q27077167
• Icosa‐5,8,11,14‐tetraynoic acid (D3)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9919	99.19%
Caco-2	-	0.6438	64.38%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5160	51.60%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	+	0.8201	82.01%
OATP1B3 inhibitior	-	0.3106	31.06%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7271	72.71%
P-glycoprotein inhibitior	-	0.8209	82.09%
P-glycoprotein substrate	-	0.9205	92.05%
CYP3A4 substrate	-	0.6561	65.61%
CYP2C9 substrate	+	0.6464	64.64%
CYP2D6 substrate	-	0.8866	88.66%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.7810	78.10%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9478	94.78%
CYP1A2 inhibition	+	0.8724	87.24%
CYP2C8 inhibition	-	0.8825	88.25%
CYP inhibitory promiscuity	-	0.9358	93.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6735	67.35%
Carcinogenicity (trinary)	Non-required	0.6833	68.33%
Eye corrosion	+	0.9569	95.69%
Eye irritation	+	0.7251	72.51%
Skin irritation	+	0.7144	71.44%
Skin corrosion	+	0.7890	78.90%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6515	65.15%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	+	0.6324	63.24%
skin sensitisation	+	0.8452	84.52%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.6998	69.98%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5162	51.62%
Acute Oral Toxicity (c)	IV	0.4480	44.80%
Estrogen receptor binding	-	0.5187	51.87%
Androgen receptor binding	-	0.7119	71.19%
Thyroid receptor binding	+	0.6740	67.40%
Glucocorticoid receptor binding	-	0.5286	52.86%
Aromatase binding	-	0.6955	69.55%
PPAR gamma	+	0.6115	61.15%
Honey bee toxicity	-	0.9886	98.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5277	52.77%
Fish aquatic toxicity	+	0.9420	94.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	3162.3 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	28183.8 nM; 1122 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	12589.3 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	1122 nM	Potency	via CMAUP
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	441.49 nM; 441.49 nM	IC50; IC50	via CMAUP; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	15848.9 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	19952.6 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	12589.3 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10000 nM; 631 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.27%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	94.83%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	93.33%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.45%	99.17%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.98%	92.08%
CHEMBL1781	P11387	DNA topoisomerase I	86.24%	97.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.85%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.06%	93.56%

Plants that contains it

• Citrus × aurantium
• Citrus deliciosa

Cross-Links

• PubChem: 1780
• NPASS: NPC158179
• ChEMBL: CHEMBL458328