Docosapentaenoic acid

Details

• Internal ID: 77fa2b3d-e93e-47ec-a5df-266602a59568
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Very long-chain fatty acids
• IUPAC Name: (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoic acid
• SMILES (Canonical): CCC=CCC=CCC=CCC=CCC=CCCCCCC(=O)O
• SMILES (Isomeric): CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCCC(=O)O
• InChI: InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChI Key: YUFFSWGQGVEMMI-JLNKQSITSA-N
• Popularity: 535 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.50 g/mol
• Exact Mass: 330.255880323 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 6.77
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 15

Synonyms

• Clupanodonic acid
• 24880-45-3
• (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoic acid
• cis-7,10,13,16,19-Docosapentaenoic acid
• 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid
• all-cis-7,10,13,16,19-Docosapentaenoic acid
• (all Z)-7,10,13,16,19-Docosapentaenoic acid
• Docosapentaenoic acid (22n-3)
• UNII-NS3OZT14QT
• NS3OZT14QT
• (7Z,10Z,13Z,16Z,19Z)-Docosapentaenoic acid
• 7,10,13,16,19-docosapentaenoic acid, (7Z,10Z,13Z,16Z,19Z)-
• 7,10,13,16,19-Docasapentaenoic acid, (all-Z)-
• Docosapentaenoic acid 22n-3
• CHEMBL496634
• CHEBI:53488
• 7,10,13,16,19-Docosapentaenoic acid, (all Z)-
• FA 22:5
• C22:5n-3,6,9,12,15
• Clupanodonate
• Docosapentaenoic
• Osbond's acid
• docosapentaenoic acid (C22:5 N3)
• SCHEMBL20748
• BSPBio_001300
• (all-cis)-7,10,13,16,19-Docosapentaenoic Acid
• BML3-C02
• (all-Z)-7, 10, 13, 16, 19-docosapentaenoic acid
• DTXSID6074758
• HMS1361A22
• HMS1791A22
• HMS1989A22
• HMS3402A22
• HMS3649F13
• BDBM50269224
• LMFA04000044
• 7,10,13,16,19-docosapentaenoate
• DOCOSAPENTAENOIC ACID [WHO-DD]
• IDI1_033770
• NCGC00161353-01
• NCGC00161353-02
• NCGC00161353-03
• LS-63382
• HY-113159
• CS-0062313
• Docosa-7c,10c,13c,16c,19c-pentaensaeure
• C22:5 (N-3)
• Delta7,10,13,16,19-Docosapentaenoic acid
• docosa-7Z,10Z,13Z,16Z,19Z-pentaenoic acid
• (all-Z)-7,10,13,16,19-Docosapentaenoic acid
• SR-01000946652
• 22:5 N-3
• J-015716
• Q3278345
• SR-01000946652-1
• FA(22:5(7Z,10Z,13Z,16Z,19Z))
• 7,10,13,16,19-Docosapentaenoic acid, (all-Z)- (8CI)
• (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoate
• (7Z,10Z,13Z,16Z,19Z)-Docosa 7,10,13,16,19-pentaenoic acid
• (7Z,10Z,13Z,16Z,19Z)-Docosa-7,10,13,16,19-pentaenoicacid
• 7,10,13,16,19-Docosapentaenoicacid,(7Z,10Z,13Z,16Z,19Z)-
• all-cis-7,10,13,16,19-Docosapentaenoic acid, synthetic, >=97%
• 7,10,13,16,19-Docosapentaenoic acid, (7Z,10Z,13Z,16Z,19Z)- (9CI)
• 244880-45-3
• Docosapentaenoic acid (cis-7,10,13,16,19), 500 mug/mL in ethanol, certified reference material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	-	0.6933	69.33%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Plasma membrane	0.5044	50.44%
OATP2B1 inhibitior	-	0.8551	85.51%
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	+	0.9103	91.03%
P-glycoprotein inhibitior	-	0.5562	55.62%
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	-	0.6685	66.85%
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	-	0.3644	36.44%
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	+	0.7888	78.88%
Androgen receptor binding	-	0.8987	89.87%
Thyroid receptor binding	-	0.4890	48.90%
Glucocorticoid receptor binding	+	0.6572	65.72%
Aromatase binding	+	0.6724	67.24%
PPAR gamma	+	0.8399	83.99%
Honey bee toxicity	-	0.9918	99.18%
Biodegradation	-	0.5250	52.50%
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
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	125.9 nM	Potency	via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	16800 nM	IC50	PMID: 16643058
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

• Schisandra chinensis

Cross-Links

• PubChem: 5497182
• NPASS: NPC70387
• ChEMBL: CHEMBL496634
• LOTUS: LTS0002529
• wikiData: Q3278345