(E)-5-[(1S,4aR,5R,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid

Details

• Internal ID: 905088f3-e798-4246-9629-97ebdf7af68c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (E)-5-[(1S,4aR,5R,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
• InChI: InChI=1S/C20H32O3/c1-14(12-18(22)23)6-8-16-15(2)7-9-17-19(3,13-21)10-5-11-20(16,17)4/h7,12,16-17,21H,5-6,8-11,13H2,1-4H3,(H,22,23)/b14-12+/t16-,17-,19-,20+/m0/s1
• InChI Key: QBPIYFGMPLYNKM-GQSMEJGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.6889	68.89%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.7818	78.18%
OATP1B3 inhibitior	-	0.2274	22.74%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5741	57.41%
BSEP inhibitior	+	0.6745	67.45%
P-glycoprotein inhibitior	-	0.8212	82.12%
P-glycoprotein substrate	-	0.7948	79.48%
CYP3A4 substrate	+	0.5986	59.86%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.9158	91.58%
CYP3A4 inhibition	-	0.6882	68.82%
CYP2C9 inhibition	-	0.6578	65.78%
CYP2C19 inhibition	-	0.7964	79.64%
CYP2D6 inhibition	-	0.9042	90.42%
CYP1A2 inhibition	-	0.8061	80.61%
CYP2C8 inhibition	-	0.6007	60.07%
CYP inhibitory promiscuity	-	0.6529	65.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6282	62.82%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8526	85.26%
Skin irritation	-	0.7480	74.80%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7404	74.04%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.5294	52.94%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8042	80.42%
Acute Oral Toxicity (c)	III	0.5748	57.48%
Estrogen receptor binding	+	0.7780	77.80%
Androgen receptor binding	+	0.5855	58.55%
Thyroid receptor binding	+	0.6247	62.47%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	+	0.5874	58.74%
PPAR gamma	+	0.6858	68.58%
Honey bee toxicity	-	0.8929	89.29%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	95.69%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.12%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.53%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.50%	96.61%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.13%	94.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.16%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.66%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.30%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.52%	95.89%
CHEMBL4040	P28482	MAP kinase ERK2	80.33%	83.82%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.12%	93.56%

Plants that contains it

• Haplopappus remyanus

Cross-Links

• PubChem: 101616658
• LOTUS: LTS0144042
• wikiData: Q105217942