2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid

Details

• Internal ID: 4232de84-20fd-434f-9715-c606e0e07144
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Salicylic acid and derivatives > Salicylic acids
• IUPAC Name: 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
• SMILES (Canonical): C=CCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• SMILES (Isomeric): C=CC/C=C\C/C=C\CCCCCCCC1=C(C(=CC=C1)O)C(=O)O
• InChI: InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
• InChI Key: QUVGEKPNSCFQIR-UTOQUPLUSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.50 g/mol
• Exact Mass: 342.21949481 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 7.60
• Atomic LogP (AlogP): 6.05
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

• 2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
• 103904-73-0
• 2-hydroxy-6-(8Z,11Z)-8,11,14-pentadecatrien-1-yl-benzoicacid
• 2-Hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trien-1-yl]benzoic acid
• (15:3)-Anacardic acid
• 2-hydroxy-6-((8Z,11Z)-pentadeca-8,11,14-trienyl)benzoic acid
• MEGxp0_000812
• SCHEMBL4142096
• ACon1_001118
• DTXSID70872877
• CHEBI:183726
• 2-Pentadecyl-6-hydroxybenzoic acid
• BDBM50292429
• LMPK15040001
• AKOS040736422
• NCGC00169660-01
• NCGC00169660-02
• Q527648
• (15:3)-Anacardic acid, >=85% (LC/MS-ELSD)
• BRD-K93380348-001-01-8
• 6[8''(Z ),11''(Z ),14''-pentadecatrienyl]salicylicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9604	96.04%
Caco-2	-	0.6870	68.70%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8226	82.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9257	92.57%
OATP1B3 inhibitior	+	0.9646	96.46%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	+	0.6076	60.76%
P-glycoprotein inhibitior	+	0.7140	71.40%
P-glycoprotein substrate	-	0.8531	85.31%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8185	81.85%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	+	0.6307	63.07%
CYP2C9 inhibition	+	0.5669	56.69%
CYP2C19 inhibition	+	0.6720	67.20%
CYP2D6 inhibition	-	0.8896	88.96%
CYP1A2 inhibition	-	0.7939	79.39%
CYP2C8 inhibition	+	0.4473	44.73%
CYP inhibitory promiscuity	-	0.6417	64.17%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8062	80.62%
Carcinogenicity (trinary)	Non-required	0.7612	76.12%
Eye corrosion	-	0.8946	89.46%
Eye irritation	-	0.6013	60.13%
Skin irritation	+	0.5468	54.68%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8508	85.08%
Micronuclear	-	0.7541	75.41%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	+	0.6809	68.09%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.5663	56.63%
Acute Oral Toxicity (c)	III	0.6643	66.43%
Estrogen receptor binding	+	0.8545	85.45%
Androgen receptor binding	+	0.5218	52.18%
Thyroid receptor binding	+	0.6183	61.83%
Glucocorticoid receptor binding	+	0.6173	61.73%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8523	85.23%
Honey bee toxicity	-	0.9496	94.96%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5476	54.76%
Fish aquatic toxicity	+	0.9942	99.42%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3784	Q09472	Histone acetyltransferase p300	5000 nM; 5000 nM	IC50; IC50	PMID: 19101154; PMID: 22100137
CHEMBL5500	Q92831	Histone acetyltransferase PCAF	667050 nM; 8500 nM; 1000000 nM	IC50; IC50; IC50	PMID: 19114310; PMID: 22100137; PMID: 20655754

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.49%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.97%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.73%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.21%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.03%	96.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	86.80%	96.25%
CHEMBL1255126	O15151	Protein Mdm4	86.26%	90.20%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.64%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.85%	96.00%
CHEMBL1781	P11387	DNA topoisomerase I	81.74%	97.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.42%	83.57%
CHEMBL3891	P07384	Calpain 1	80.53%	93.04%

Plants that contains it

• Anacardium occidentale
• Aronia arbutifolia
• Clibadium sodiroi
• Discaria serratifolia
• Pteris dactylina
• Pyrostegia venusta
• Rostellularia hayatae
• Silene viscaria

Cross-Links

• PubChem: 9875131
• NPASS: NPC184579
• ChEMBL: CHEMBL455368
• LOTUS: LTS0149518
• wikiData: Q527648