[4-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]-3,6-dioxocyclohexa-1,4-dien-1-yl] 3-methylbutanoate

Details

• Internal ID: 72031b77-0c8d-4437-932e-2d2ee28f067d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [4-hydroxy-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]-3,6-dioxocyclohexa-1,4-dien-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC1=C(C(=O)C(=C(C1=O)O)C(C)CCC=C(C)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC1=C(C(=O)C(=C(C1=O)O)[C@H](C)CCC=C(C)C)OC(=O)CC(C)C
• InChI: InChI=1S/C20H28O5/c1-11(2)8-7-9-13(5)16-18(23)17(22)14(6)20(19(16)24)25-15(21)10-12(3)4/h8,12-13,23H,7,9-10H2,1-6H3/t13-/m1/s1
• InChI Key: GOQGLFQEYAYJCF-CYBMUJFWSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.20
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9568	95.68%
Caco-2	+	0.8753	87.53%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8467	84.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8814	88.14%
OATP1B3 inhibitior	+	0.8989	89.89%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5710	57.10%
P-glycoprotein inhibitior	-	0.4470	44.70%
P-glycoprotein substrate	-	0.7852	78.52%
CYP3A4 substrate	+	0.5348	53.48%
CYP2C9 substrate	-	0.7883	78.83%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.8502	85.02%
CYP2C9 inhibition	-	0.8025	80.25%
CYP2C19 inhibition	-	0.7597	75.97%
CYP2D6 inhibition	-	0.8389	83.89%
CYP1A2 inhibition	-	0.8339	83.39%
CYP2C8 inhibition	-	0.9396	93.96%
CYP inhibitory promiscuity	-	0.9057	90.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7509	75.09%
Carcinogenicity (trinary)	Non-required	0.6644	66.44%
Eye corrosion	-	0.9767	97.67%
Eye irritation	-	0.7207	72.07%
Skin irritation	-	0.5698	56.98%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5968	59.68%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6292	62.92%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.5922	59.22%
Acute Oral Toxicity (c)	III	0.6955	69.55%
Estrogen receptor binding	-	0.5336	53.36%
Androgen receptor binding	-	0.5147	51.47%
Thyroid receptor binding	-	0.5401	54.01%
Glucocorticoid receptor binding	+	0.6976	69.76%
Aromatase binding	-	0.6928	69.28%
PPAR gamma	+	0.8365	83.65%
Honey bee toxicity	-	0.8412	84.12%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9707	97.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.27%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.65%	95.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.54%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	92.36%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.08%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.72%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	86.31%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.75%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.40%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.04%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.03%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.76%	90.71%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.24%	90.93%

Plants that contains it

• Jungia stuebelii

Cross-Links

• PubChem: 163003616
• LOTUS: LTS0118776
• wikiData: Q105014392