(2S)-2-[(2E,6Z)-8-hydroxy-6-methylocta-2,6-dien-2-yl]-5-(4-methylpent-3-enyl)-2,3-dihydropyran-6-one

Details

• Internal ID: b45c4025-2a47-4182-8bf2-b57f128e3843
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (2S)-2-[(2E,6Z)-8-hydroxy-6-methylocta-2,6-dien-2-yl]-5-(4-methylpent-3-enyl)-2,3-dihydropyran-6-one
• SMILES (Canonical): CC(=CCCC1=CCC(OC1=O)C(=CCCC(=CCO)C)C)C
• SMILES (Isomeric): CC(=CCCC1=CC[C@H](OC1=O)/C(=C/CC/C(=C\CO)/C)/C)C
• InChI: InChI=1S/C20H30O3/c1-15(2)7-5-10-18-11-12-19(23-20(18)22)17(4)9-6-8-16(3)13-14-21/h7,9,11,13,19,21H,5-6,8,10,12,14H2,1-4H3/b16-13-,17-9+/t19-/m0/s1
• InChI Key: PSWJKRAGHBXOTJ-IWQVTKTNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9641	96.41%
Caco-2	+	0.8766	87.66%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8592	85.92%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.7412	74.12%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8800	88.00%
P-glycoprotein inhibitior	-	0.5664	56.64%
P-glycoprotein substrate	-	0.8670	86.70%
CYP3A4 substrate	+	0.5518	55.18%
CYP2C9 substrate	+	0.5858	58.58%
CYP2D6 substrate	-	0.8826	88.26%
CYP3A4 inhibition	-	0.6660	66.60%
CYP2C9 inhibition	-	0.8108	81.08%
CYP2C19 inhibition	-	0.7088	70.88%
CYP2D6 inhibition	-	0.8509	85.09%
CYP1A2 inhibition	-	0.5915	59.15%
CYP2C8 inhibition	-	0.8509	85.09%
CYP inhibitory promiscuity	-	0.8950	89.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9228	92.28%
Carcinogenicity (trinary)	Non-required	0.6972	69.72%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.5809	58.09%
Skin irritation	-	0.6497	64.97%
Skin corrosion	-	0.9652	96.52%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7695	76.95%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.5484	54.84%
skin sensitisation	-	0.6534	65.34%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	-	0.6222	62.22%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5439	54.39%
Acute Oral Toxicity (c)	III	0.6614	66.14%
Estrogen receptor binding	+	0.5309	53.09%
Androgen receptor binding	-	0.6722	67.22%
Thyroid receptor binding	+	0.5919	59.19%
Glucocorticoid receptor binding	-	0.5755	57.55%
Aromatase binding	-	0.5434	54.34%
PPAR gamma	+	0.7015	70.15%
Honey bee toxicity	-	0.9112	91.12%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9295	92.95%

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	95.38%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.06%	83.82%
CHEMBL2581	P07339	Cathepsin D	91.58%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.04%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.62%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.45%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.95%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.09%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.95%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.12%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.55%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.52%	97.25%

Plants that contains it

• Ichthyothere mollis

Cross-Links

• PubChem: 162988441
• LOTUS: LTS0127268
• wikiData: Q105214445