4-O-[5-[5-(acetyloxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] 1-O-methyl butanedioate

Details

• Internal ID: d9e835bf-d9c8-4495-86f6-007b4f239b08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 4-O-[5-[5-(acetyloxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] 1-O-methyl butanedioate
• SMILES (Canonical): CC1=CCC2C(CCCC2(C1CCC(=CCOC(=O)CCC(=O)OC)C)C)(C)COC(=O)C
• SMILES (Isomeric): CC1=CCC2C(CCCC2(C1CCC(=CCOC(=O)CCC(=O)OC)C)C)(C)COC(=O)C
• InChI: InChI=1S/C27H42O6/c1-19(14-17-32-25(30)13-12-24(29)31-6)8-10-22-20(2)9-11-23-26(4,18-33-21(3)28)15-7-16-27(22,23)5/h9,14,22-23H,7-8,10-13,15-18H2,1-6H3
• InChI Key: JBKOFQXECNQYPG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₂O₆
• Molecular Weight: 462.60 g/mol
• Exact Mass: 462.29813906 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.55
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9847	98.47%
Caco-2	-	0.5696	56.96%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8269	82.69%
OATP1B3 inhibitior	+	0.9186	91.86%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9886	98.86%
P-glycoprotein inhibitior	+	0.8252	82.52%
P-glycoprotein substrate	-	0.5977	59.77%
CYP3A4 substrate	+	0.6681	66.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.7729	77.29%
CYP2C9 inhibition	-	0.8735	87.35%
CYP2C19 inhibition	-	0.7740	77.40%
CYP2D6 inhibition	-	0.9304	93.04%
CYP1A2 inhibition	-	0.8676	86.76%
CYP2C8 inhibition	+	0.5840	58.40%
CYP inhibitory promiscuity	-	0.6711	67.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8220	82.20%
Carcinogenicity (trinary)	Non-required	0.5770	57.70%
Eye corrosion	-	0.9790	97.90%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.7858	78.58%
Skin corrosion	-	0.9864	98.64%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7419	74.19%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7609	76.09%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6521	65.21%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7676	76.76%
Acute Oral Toxicity (c)	III	0.5847	58.47%
Estrogen receptor binding	+	0.6799	67.99%
Androgen receptor binding	+	0.5468	54.68%
Thyroid receptor binding	-	0.5179	51.79%
Glucocorticoid receptor binding	+	0.7317	73.17%
Aromatase binding	+	0.5625	56.25%
PPAR gamma	+	0.6375	63.75%
Honey bee toxicity	-	0.7980	79.80%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	97.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.00%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	88.89%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.50%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	87.21%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.98%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.54%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.90%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.86%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.33%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.01%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.76%	92.62%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.70%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.67%	95.89%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	83.52%	91.65%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.49%	91.07%
CHEMBL5028	O14672	ADAM10	82.98%	97.50%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.61%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.36%	99.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.79%	82.69%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.04%	98.99%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.78%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.75%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.35%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.18%	92.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.12%	97.50%

Plants that contains it

• Acamptopappus sphaerocephalus

Cross-Links

• PubChem: 163074647
• LOTUS: LTS0090295
• wikiData: Q105124406