2-[(2E,6E,8R,9R,10E)-8,9-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-6-methylcyclohexa-2,5-diene-1,4-dione

Details

• Internal ID: 6d93d577-b948-47e5-adc2-0873a4ad1ab5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2E,6E,8R,9R,10E)-8,9-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]-6-methylcyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CC1=CC(=O)C=C(C1=O)CC=C(C)CCC=C(C)C(C(C=C(C)CCC=C(C)C)O)O
• SMILES (Isomeric): CC1=CC(=O)C=C(C1=O)C/C=C(\C)/CC/C=C(\C)/[C@H]([C@@H](/C=C(\C)/CCC=C(C)C)O)O
• InChI: InChI=1S/C27H38O4/c1-18(2)9-7-11-20(4)15-25(29)27(31)21(5)12-8-10-19(3)13-14-23-17-24(28)16-22(6)26(23)30/h9,12-13,15-17,25,27,29,31H,7-8,10-11,14H2,1-6H3/b19-13+,20-15+,21-12+/t25-,27-/m1/s1
• InChI Key: QVPQLWXTCHXBRT-KTLGNFHWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₄
• Molecular Weight: 426.60 g/mol
• Exact Mass: 426.27700969 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.49
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9465	94.65%
Caco-2	-	0.5580	55.80%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8666	86.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8895	88.95%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9382	93.82%
P-glycoprotein inhibitior	+	0.7488	74.88%
P-glycoprotein substrate	-	0.7620	76.20%
CYP3A4 substrate	+	0.5567	55.67%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8521	85.21%
CYP3A4 inhibition	-	0.7264	72.64%
CYP2C9 inhibition	-	0.6736	67.36%
CYP2C19 inhibition	-	0.7577	75.77%
CYP2D6 inhibition	-	0.6398	63.98%
CYP1A2 inhibition	-	0.7328	73.28%
CYP2C8 inhibition	-	0.8354	83.54%
CYP inhibitory promiscuity	-	0.8980	89.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8423	84.23%
Carcinogenicity (trinary)	Non-required	0.7189	71.89%
Eye corrosion	-	0.9803	98.03%
Eye irritation	-	0.9472	94.72%
Skin irritation	-	0.5724	57.24%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6908	69.08%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5458	54.58%
skin sensitisation	+	0.5522	55.22%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5700	57.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6606	66.06%
Acute Oral Toxicity (c)	III	0.6823	68.23%
Estrogen receptor binding	+	0.7372	73.72%
Androgen receptor binding	+	0.5569	55.69%
Thyroid receptor binding	+	0.5192	51.92%
Glucocorticoid receptor binding	+	0.5949	59.49%
Aromatase binding	+	0.5252	52.52%
PPAR gamma	+	0.6851	68.51%
Honey bee toxicity	-	0.8073	80.73%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9961	99.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.79%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	92.37%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.45%	95.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.62%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.16%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.35%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	81.03%	94.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 14683210
• LOTUS: LTS0249401
• wikiData: Q105228829