(2R)-2-[(2E,6Z)-8-hydroxy-6-(hydroxymethyl)-2-methylocta-2,6-dienyl]-4-(4-methylpent-3-enyl)-2H-furan-5-one

Details

• Internal ID: d4c89b5d-385e-4dcf-831e-e709022c8033
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2R)-2-[(2E,6Z)-8-hydroxy-6-(hydroxymethyl)-2-methylocta-2,6-dienyl]-4-(4-methylpent-3-enyl)-2H-furan-5-one
• SMILES (Canonical): CC(=CCCC1=CC(OC1=O)CC(=CCCC(=CCO)CO)C)C
• SMILES (Isomeric): CC(=CCCC1=C[C@H](OC1=O)C/C(=C/CC/C(=C/CO)/CO)/C)C
• InChI: InChI=1S/C20H30O4/c1-15(2)6-4-9-18-13-19(24-20(18)23)12-16(3)7-5-8-17(14-22)10-11-21/h6-7,10,13,19,21-22H,4-5,8-9,11-12,14H2,1-3H3/b16-7+,17-10-/t19-/m1/s1
• InChI Key: QNEQTAOUNJRRBL-LMMFWFPESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.61
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9433	94.33%
Caco-2	+	0.5636	56.36%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8168	81.68%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8604	86.04%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.7412	74.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8702	87.02%
P-glycoprotein inhibitior	-	0.5363	53.63%
P-glycoprotein substrate	-	0.7237	72.37%
CYP3A4 substrate	+	0.5822	58.22%
CYP2C9 substrate	+	0.5858	58.58%
CYP2D6 substrate	-	0.8826	88.26%
CYP3A4 inhibition	-	0.6473	64.73%
CYP2C9 inhibition	-	0.8602	86.02%
CYP2C19 inhibition	-	0.8212	82.12%
CYP2D6 inhibition	-	0.8832	88.32%
CYP1A2 inhibition	-	0.7507	75.07%
CYP2C8 inhibition	-	0.8266	82.66%
CYP inhibitory promiscuity	-	0.8616	86.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9528	95.28%
Carcinogenicity (trinary)	Non-required	0.6637	66.37%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.7789	77.89%
Skin irritation	-	0.6992	69.92%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5238	52.38%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.8320	83.20%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	-	0.5608	56.08%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5538	55.38%
Acute Oral Toxicity (c)	III	0.5621	56.21%
Estrogen receptor binding	+	0.6617	66.17%
Androgen receptor binding	-	0.6626	66.26%
Thyroid receptor binding	+	0.6150	61.50%
Glucocorticoid receptor binding	+	0.5440	54.40%
Aromatase binding	+	0.5229	52.29%
PPAR gamma	+	0.7715	77.15%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9591	95.91%

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	95.20%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.36%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.08%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.26%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.47%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.24%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.03%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.48%	99.23%

Plants that contains it

• Diplostephium meyenii

Cross-Links

• PubChem: 162903719
• LOTUS: LTS0002674
• wikiData: Q105224364