9,12,15-Octadecatrienoic acid

Details

• Internal ID: 3e8e5249-46b1-4258-9c2d-61e4294f2801
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: octadeca-9,12,15-trienoic acid
• SMILES (Canonical): CCC=CCC=CCC=CCCCCCCCC(=O)O
• SMILES (Isomeric): CCC=CCC=CCC=CCCCCCCCC(=O)O
• InChI: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)
• InChI Key: DTOSIQBPPRVQHS-UHFFFAOYSA-N
• Popularity: 2,823 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.40 g/mol
• Exact Mass: 278.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.66
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 13

Synonyms

• 9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-
• |A-Lnn
• CBiol_001952
• KBioGR_000096
• KBioSS_000096
• 9,12,15-octadecatrienic acid
• 9,12,15-octadectrienoic acid
• CHEMBL3560296
• DTXSID7075058
• KBio2_000096
• KBio2_002664
• KBio2_005232
• KBio3_000191
• KBio3_000192
• DTOSIQBPPRVQHS-UHFFFAOYSA-N
• Bio1_000238
• Bio1_000727
• Bio1_001216
• Bio2_000096
• Bio2_000576
• BCP18966
• AKOS028108942
• NCGC00091058-11
• FT-0622170
• FT-0670799
• Q27164304

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.6071	60.71%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Plasma membrane	0.5044	50.44%
OATP2B1 inhibitior	-	0.8530	85.30%
OATP1B1 inhibitior	-	0.4580	45.80%
OATP1B3 inhibitior	-	0.3406	34.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5594	55.94%
P-glycoprotein inhibitior	-	0.8342	83.42%
P-glycoprotein substrate	-	0.9574	95.74%
CYP3A4 substrate	-	0.6597	65.97%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.9465	94.65%
CYP2C9 inhibition	-	0.8798	87.98%
CYP2C19 inhibition	-	0.9638	96.38%
CYP2D6 inhibition	-	0.9631	96.31%
CYP1A2 inhibition	+	0.6915	69.15%
CYP2C8 inhibition	-	0.9243	92.43%
CYP inhibitory promiscuity	-	0.9426	94.26%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6935	69.35%
Carcinogenicity (trinary)	Non-required	0.6373	63.73%
Eye corrosion	+	0.9371	93.71%
Eye irritation	+	0.8357	83.57%
Skin irritation	+	0.7676	76.76%
Skin corrosion	-	0.6260	62.60%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3603	36.03%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	+	0.8470	84.70%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	-	0.6531	65.31%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8766	87.66%
Acute Oral Toxicity (c)	IV	0.6387	63.87%
Estrogen receptor binding	+	0.5761	57.61%
Androgen receptor binding	-	0.8917	89.17%
Thyroid receptor binding	+	0.6398	63.98%
Glucocorticoid receptor binding	-	0.7344	73.44%
Aromatase binding	-	0.4910	49.10%
PPAR gamma	+	0.8890	88.90%
Honey bee toxicity	-	0.9918	99.18%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8175	81.75%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	125.9 nM	Potency	via Super-PRED
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	7.9 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	96.97%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.31%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.53%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	90.68%	97.00%
CHEMBL221	P23219	Cyclooxygenase-1	89.12%	90.17%

Plants that contains it

• Abelmoschus esculentus
• Abrus precatorius
• Allium obliquum
• Arnica montana
• Artemisia capillaris
• Azadirachta indica
• Bidens pilosa
• Brachylaena discolor var. transvaalensis
• Capparis spinosa
• Celastrus paniculatus
• Chamaecyparis formosensis
• Croton cortesianus
• Cucumis melo
• Descurainia sophia
• Dipteryx lacunifera
• Echinacea purpurea
• Elaeagnus angustifolia
• Fernandoa adenophylla
• Ginkgo biloba
• Gymnanthemum myrianthum
• Inezia integrifolia
• Isatis tinctoria
• Jodina rhombifolia
• Lallemantia iberica
• Lallemantia royleana
• Lepidium apetalum
• Lessingianthus compactiflorus
• Ligularia macrophylla
• Lycium barbarum
• Lycium chinense
• Malva sylvestris
• Mentha spicata
• Mikania goyazensis
• Neolitsea hiiranensis
• Nicotiana tabacum
• Nigella sativa
• Pinus resinosa
• Plantago asiatica
• Plantago depressa
• Punica granatum
• Raphanus raphanistrum subsp. sativus
• Rhytidiadelphus squarrosus
• Salmea scandens
• Saussurea medusa
• Schotia brachypetala
• Scurrula atropurpurea
• Senecio subrubriflorus
• Terminalia chebula
• Typha domingensis
• Ziziphora pedicellata

Cross-Links

• PubChem: 860
• NPASS: NPC1813
• LOTUS: LTS0216950
• wikiData: Q27164304