Centipedic acid

Details

• Internal ID: 01c14227-f2fa-4eb7-92f9-bcf2eb6d7bf5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2Z,6E)-9-(furan-3-yl)-6-methyl-2-(4-methylpent-3-enyl)nona-2,6-dienoic acid
• SMILES (Canonical): CC(=CCCC(=CCCC(=CCCC1=COC=C1)C)C(=O)O)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC/C(=C/CCC1=COC=C1)/C)/C(=O)O)C
• InChI: InChI=1S/C20H28O3/c1-16(2)7-4-11-19(20(21)22)12-6-9-17(3)8-5-10-18-13-14-23-15-18/h7-8,12-15H,4-6,9-11H2,1-3H3,(H,21,22)/b17-8+,19-12-
• InChI Key: UKHQJOTZHQQZBX-BAOHTXIFSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.70
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• Centipedic acid
• CHEMBL1989337
• NSC-640324
• (2Z,6E)-9-(furan-3-yl)-6-methyl-2-(4-methylpent-3-enyl)nona-2,6-dienoic acid
• 9-(3-Furyl)-6-methyl-2-(4-methyl-3-pentenyl)-2,6-nonadienoic acid
• (2Z,6E)-9-(3-furyl)-6-methyl-2-(4-methylpent-3-enyl)nona-2,6-dienoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.6266	62.66%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5889	58.89%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.7739	77.39%
OATP1B3 inhibitior	+	0.8807	88.07%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9250	92.50%
P-glycoprotein inhibitior	-	0.6225	62.25%
P-glycoprotein substrate	-	0.8784	87.84%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7818	78.18%
CYP2D6 substrate	-	0.9097	90.97%
CYP3A4 inhibition	-	0.6650	66.50%
CYP2C9 inhibition	-	0.5752	57.52%
CYP2C19 inhibition	-	0.6589	65.89%
CYP2D6 inhibition	-	0.8945	89.45%
CYP1A2 inhibition	-	0.5427	54.27%
CYP2C8 inhibition	-	0.7482	74.82%
CYP inhibitory promiscuity	-	0.6786	67.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7728	77.28%
Carcinogenicity (trinary)	Non-required	0.6130	61.30%
Eye corrosion	-	0.9212	92.12%
Eye irritation	-	0.8138	81.38%
Skin irritation	-	0.6005	60.05%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3786	37.86%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5427	54.27%
skin sensitisation	+	0.5104	51.04%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5077	50.77%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.5890	58.90%
Acute Oral Toxicity (c)	III	0.6137	61.37%
Estrogen receptor binding	+	0.5360	53.60%
Androgen receptor binding	-	0.5817	58.17%
Thyroid receptor binding	+	0.5832	58.32%
Glucocorticoid receptor binding	+	0.5393	53.93%
Aromatase binding	+	0.6275	62.75%
PPAR gamma	+	0.8606	86.06%
Honey bee toxicity	-	0.9295	92.95%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	96.66%	92.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.01%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	92.43%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.00%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.93%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.84%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.17%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.14%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	83.64%	90.17%

Plants that contains it

• Egletes viscosa
• Grangea maderaspatana
• Laennecia coulteri
• Nidorella welwitschii
• Sphaeromorphaea australis

Cross-Links

• PubChem: 5466638
• LOTUS: LTS0167731
• wikiData: Q104397306