2-[(2E,6E,9E,11S)-11-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,9,14-tetraenyl]-6-methylbenzene-1,4-diol

Details

• Internal ID: 3be9bdee-5cdf-495a-8d88-758f56ba80da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2E,6E,9E,11S)-11-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,9,14-tetraenyl]-6-methylbenzene-1,4-diol
• SMILES (Canonical): CC1=CC(=CC(=C1O)CC=C(C)CCC=C(C)CC=CC(C)(CCC=C(C)C)O)O
• SMILES (Isomeric): CC1=CC(=CC(=C1O)C/C=C(\C)/CC/C=C(\C)/C/C=C/[C@](C)(CCC=C(C)C)O)O
• InChI: InChI=1S/C27H40O3/c1-20(2)10-8-16-27(6,30)17-9-13-21(3)11-7-12-22(4)14-15-24-19-25(28)18-23(5)26(24)29/h9-11,14,17-19,28-30H,7-8,12-13,15-16H2,1-6H3/b17-9+,21-11+,22-14+/t27-/m0/s1
• InChI Key: XBSFKKHIMQOPQZ-ZDKFSMGMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₃
• Molecular Weight: 412.60 g/mol
• Exact Mass: 412.29774513 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 7.60
• Atomic LogP (AlogP): 7.07
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	-	0.5774	57.74%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8379	83.79%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8323	83.23%
OATP1B3 inhibitior	+	0.9576	95.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9436	94.36%
P-glycoprotein inhibitior	+	0.6740	67.40%
P-glycoprotein substrate	-	0.7933	79.33%
CYP3A4 substrate	+	0.5664	56.64%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.6974	69.74%
CYP3A4 inhibition	+	0.5887	58.87%
CYP2C9 inhibition	-	0.6751	67.51%
CYP2C19 inhibition	-	0.5723	57.23%
CYP2D6 inhibition	-	0.8917	89.17%
CYP1A2 inhibition	-	0.5832	58.32%
CYP2C8 inhibition	+	0.5317	53.17%
CYP inhibitory promiscuity	-	0.5100	51.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7539	75.39%
Carcinogenicity (trinary)	Non-required	0.6592	65.92%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.8741	87.41%
Skin irritation	-	0.6285	62.85%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7842	78.42%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	+	0.6440	64.40%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7343	73.43%
Acute Oral Toxicity (c)	III	0.7410	74.10%
Estrogen receptor binding	+	0.7179	71.79%
Androgen receptor binding	+	0.5192	51.92%
Thyroid receptor binding	+	0.7304	73.04%
Glucocorticoid receptor binding	+	0.6789	67.89%
Aromatase binding	+	0.7262	72.62%
PPAR gamma	+	0.8228	82.28%
Honey bee toxicity	-	0.8152	81.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	97.51%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	95.17%	92.08%
CHEMBL2581	P07339	Cathepsin D	92.81%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	90.73%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.60%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.00%	86.33%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	84.79%	92.68%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	83.28%	83.57%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.46%	93.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.85%	89.00%

Plants that contains it

• Alstonia macrophylla
• Alstonia muelleriana

Cross-Links

• PubChem: 163194694
• LOTUS: LTS0125462
• wikiData: Q104888933