[(1S,4aR,5S,6S,8aS)-6-hydroxy-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a,6-trimethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl 3-methylbut-2-enoate

Details

• Internal ID: 17d7785e-a036-449f-bfe2-dd34cf9a32e3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(1S,4aR,5S,6S,8aS)-6-hydroxy-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a,6-trimethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl 3-methylbut-2-enoate
• SMILES (Canonical): CC(CCC1C2(CCCC(C2CCC1(C)O)(C)COC(=O)C=C(C)C)C)CCO
• SMILES (Isomeric): C[C@@H](CC[C@H]1[C@@]2(CCC[C@]([C@H]2CC[C@]1(C)O)(C)COC(=O)C=C(C)C)C)CCO
• InChI: InChI=1S/C25H44O4/c1-18(2)16-22(27)29-17-23(4)12-7-13-24(5)20(23)10-14-25(6,28)21(24)9-8-19(3)11-15-26/h16,19-21,26,28H,7-15,17H2,1-6H3/t19-,20+,21-,23+,24+,25-/m0/s1
• InChI Key: DNPNGMPLSLKKCQ-AHSVDLCGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₄₄O₄
• Molecular Weight: 408.60 g/mol
• Exact Mass: 408.32395988 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.27
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.5626	56.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8770	87.70%
OATP2B1 inhibitior	-	0.7276	72.76%
OATP1B1 inhibitior	+	0.8622	86.22%
OATP1B3 inhibitior	-	0.2199	21.99%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6369	63.69%
BSEP inhibitior	+	0.7566	75.66%
P-glycoprotein inhibitior	-	0.5179	51.79%
P-glycoprotein substrate	-	0.5852	58.52%
CYP3A4 substrate	+	0.6652	66.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9172	91.72%
CYP3A4 inhibition	-	0.7960	79.60%
CYP2C9 inhibition	-	0.8517	85.17%
CYP2C19 inhibition	-	0.8956	89.56%
CYP2D6 inhibition	-	0.9264	92.64%
CYP1A2 inhibition	-	0.8912	89.12%
CYP2C8 inhibition	-	0.6920	69.20%
CYP inhibitory promiscuity	-	0.8612	86.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6919	69.19%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9411	94.11%
Skin irritation	-	0.6401	64.01%
Skin corrosion	-	0.9762	97.62%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4343	43.43%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7223	72.23%
skin sensitisation	-	0.7616	76.16%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8310	83.10%
Acute Oral Toxicity (c)	III	0.7615	76.15%
Estrogen receptor binding	+	0.8396	83.96%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5724	57.24%
Glucocorticoid receptor binding	+	0.7629	76.29%
Aromatase binding	+	0.6710	67.10%
PPAR gamma	+	0.7874	78.74%
Honey bee toxicity	-	0.8057	80.57%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7755	77.55%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.46%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.43%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.96%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.36%	89.05%
CHEMBL237	P41145	Kappa opioid receptor	90.87%	98.10%
CHEMBL2581	P07339	Cathepsin D	90.71%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.05%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	89.00%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.85%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.54%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.80%	95.89%
CHEMBL325	Q13547	Histone deacetylase 1	84.68%	95.92%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.18%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.82%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.64%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	83.56%	94.75%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.32%	91.24%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.30%	82.69%
CHEMBL5255	O00206	Toll-like receptor 4	83.02%	92.50%
CHEMBL3524	P56524	Histone deacetylase 4	82.47%	92.97%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.38%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.21%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.19%	96.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.75%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.67%	96.47%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.26%	91.07%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.22%	96.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.06%	94.33%

Plants that contains it

• Olearia teretifolia

Cross-Links

• PubChem: 163005921
• LOTUS: LTS0017067
• wikiData: Q104985685