3-[(3S)-5-[(1S,2S,4aS,5S,8aR)-2-hydroxy-2,5,8a-trimethyl-5-[[(Z)-2-methylbut-2-enoyl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentoxy]-3-oxopropanoic acid

Details

• Internal ID: 39e80f08-3e65-4e24-9c52-6edddf07b85e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 3-[(3S)-5-[(1S,2S,4aS,5S,8aR)-2-hydroxy-2,5,8a-trimethyl-5-[[(Z)-2-methylbut-2-enoyl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentoxy]-3-oxopropanoic acid
• SMILES (Canonical): CC=C(C)C(=O)OCC1(CCCC2(C1CCC(C2CCC(C)CCOC(=O)CC(=O)O)(C)O)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC[C@]1(CCC[C@@]2([C@@H]1CC[C@]([C@H]2CC[C@H](C)CCOC(=O)CC(=O)O)(C)O)C)C
• InChI: InChI=1S/C28H46O7/c1-7-20(3)25(32)35-18-26(4)13-8-14-27(5)21(26)11-15-28(6,33)22(27)10-9-19(2)12-16-34-24(31)17-23(29)30/h7,19,21-22,33H,8-18H2,1-6H3,(H,29,30)/b20-7-/t19-,21+,22-,26+,27+,28-/m0/s1
• InChI Key: SZWLIXDZSIBNOJ-ILDDZXLDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₆O₇
• Molecular Weight: 494.70 g/mol
• Exact Mass: 494.32435380 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.29
• H-Bond Acceptor: 6
• 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	+	0.9810	98.10%
Caco-2	-	0.6424	64.24%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8821	88.21%
OATP2B1 inhibitior	-	0.7075	70.75%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	+	0.8997	89.97%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6890	68.90%
BSEP inhibitior	+	0.8849	88.49%
P-glycoprotein inhibitior	+	0.7041	70.41%
P-glycoprotein substrate	-	0.5370	53.70%
CYP3A4 substrate	+	0.6842	68.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9211	92.11%
CYP3A4 inhibition	-	0.8161	81.61%
CYP2C9 inhibition	-	0.9073	90.73%
CYP2C19 inhibition	-	0.8981	89.81%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.8669	86.69%
CYP2C8 inhibition	-	0.5729	57.29%
CYP inhibitory promiscuity	-	0.9357	93.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6270	62.70%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.8930	89.30%
Skin irritation	-	0.5285	52.85%
Skin corrosion	-	0.9713	97.13%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3692	36.92%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6505	65.05%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7715	77.15%
Acute Oral Toxicity (c)	III	0.5115	51.15%
Estrogen receptor binding	+	0.7341	73.41%
Androgen receptor binding	-	0.5122	51.22%
Thyroid receptor binding	-	0.5083	50.83%
Glucocorticoid receptor binding	+	0.7521	75.21%
Aromatase binding	+	0.7283	72.83%
PPAR gamma	+	0.5901	59.01%
Honey bee toxicity	-	0.7779	77.79%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9943	99.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.31%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	98.45%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.43%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.57%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	92.82%	96.47%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.22%	95.17%
CHEMBL340	P08684	Cytochrome P450 3A4	91.97%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.94%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.69%	94.62%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	90.16%	96.00%
CHEMBL2581	P07339	Cathepsin D	88.80%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.21%	82.69%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.06%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.80%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.37%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.28%	98.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.60%	93.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.06%	85.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.52%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.46%	94.33%
CHEMBL5028	O14672	ADAM10	83.82%	97.50%
CHEMBL4302	P08183	P-glycoprotein 1	83.33%	92.98%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.24%	91.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.05%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.91%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.51%	96.61%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.39%	89.34%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.26%	99.17%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.00%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.05%	89.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.63%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.09%	96.90%

Plants that contains it

• Olearia teretifolia

Cross-Links

• PubChem: 163011165
• LOTUS: LTS0149488
• wikiData: Q105264443