(2E,4E,6E,8E,10E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-5,9-dimethylundeca-2,4,6,8,10-pentaenal

Details

• Internal ID: 53095dbf-53cf-4b83-9deb-28082df5715c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2E,4E,6E,8E,10E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-5,9-dimethylundeca-2,4,6,8,10-pentaenal
• SMILES (Canonical): CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=O)C)C
• SMILES (Isomeric): CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=O)/C)/C
• InChI: InChI=1S/C22H30O2/c1-17(9-6-7-14-23)10-8-11-18(2)12-13-21-19(3)15-20(24)16-22(21,4)5/h6-14,20,24H,15-16H2,1-5H3/b7-6+,10-8+,13-12+,17-9+,18-11+/t20-/m1/s1
• InChI Key: BCNPTKKIVMTZFO-UWYNECTCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₂
• Molecular Weight: 326.50 g/mol
• Exact Mass: 326.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.24
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Apo-14'-zeaxanthinal
• CHEBI:143060
• QVM

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7857	78.57%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7261	72.61%
OATP2B1 inhibitior	-	0.7167	71.67%
OATP1B1 inhibitior	+	0.7961	79.61%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9875	98.75%
P-glycoprotein inhibitior	-	0.6006	60.06%
P-glycoprotein substrate	-	0.7502	75.02%
CYP3A4 substrate	+	0.6303	63.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.8941	89.41%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.8071	80.71%
CYP2D6 inhibition	-	0.9447	94.47%
CYP1A2 inhibition	-	0.9162	91.62%
CYP2C8 inhibition	-	0.7788	77.88%
CYP inhibitory promiscuity	-	0.9130	91.30%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7057	70.57%
Carcinogenicity (trinary)	Non-required	0.5606	56.06%
Eye corrosion	-	0.9431	94.31%
Eye irritation	-	0.9114	91.14%
Skin irritation	+	0.6254	62.54%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8171	81.71%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6841	68.41%
skin sensitisation	+	0.9201	92.01%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.7956	79.56%
Acute Oral Toxicity (c)	III	0.8385	83.85%
Estrogen receptor binding	+	0.8230	82.30%
Androgen receptor binding	+	0.5326	53.26%
Thyroid receptor binding	+	0.7587	75.87%
Glucocorticoid receptor binding	+	0.6417	64.17%
Aromatase binding	+	0.7765	77.65%
PPAR gamma	+	0.8062	80.62%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.8802	88.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.38%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.25%	91.11%
CHEMBL1870	P28702	Retinoid X receptor beta	86.39%	95.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.85%	94.75%
CHEMBL2004	P48443	Retinoid X receptor gamma	83.73%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.69%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.14%	91.71%
CHEMBL2581	P07339	Cathepsin D	83.07%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.01%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.06%	86.33%

Plants that contains it

• Capsicum annuum

Cross-Links

• PubChem: 101716226
• LOTUS: LTS0015467
• wikiData: Q104923522