(3R)-5-[(1S,4aR,6S,8aR)-6-hydroxy-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: f201aa9a-a370-403b-ad41-6c5f99ff9534
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3R)-5-[(1S,4aR,6S,8aR)-6-hydroxy-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC1=CCC2C(C(CCC2(C1CCC(C)CC(=O)O)C)O)(C)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@H]1CC[C@@H](C)CC(=O)O)(CC[C@@H](C2(C)C)O)C
• InChI: InChI=1S/C20H34O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h7,13,15-17,21H,6,8-12H2,1-5H3,(H,22,23)/t13-,15+,16+,17+,20-/m1/s1
• InChI Key: LAGHKRLLDKVJHS-FHXVVSRQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₃
• Molecular Weight: 322.50 g/mol
• Exact Mass: 322.25079494 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.65
• 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	+	0.9965	99.65%
Caco-2	+	0.6397	63.97%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8401	84.01%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.9262	92.62%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.5717	57.17%
P-glycoprotein inhibitior	-	0.8471	84.71%
P-glycoprotein substrate	-	0.7923	79.23%
CYP3A4 substrate	+	0.6199	61.99%
CYP2C9 substrate	-	0.8404	84.04%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	-	0.7599	75.99%
CYP2C9 inhibition	-	0.9210	92.10%
CYP2C19 inhibition	-	0.9012	90.12%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.9501	95.01%
CYP2C8 inhibition	-	0.9194	91.94%
CYP inhibitory promiscuity	-	0.8315	83.15%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6612	66.12%
Eye corrosion	-	0.9957	99.57%
Eye irritation	-	0.9102	91.02%
Skin irritation	+	0.6034	60.34%
Skin corrosion	-	0.9695	96.95%
Ames mutagenesis	-	0.8637	86.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4942	49.42%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5044	50.44%
skin sensitisation	+	0.5964	59.64%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7794	77.94%
Acute Oral Toxicity (c)	III	0.7784	77.84%
Estrogen receptor binding	+	0.5465	54.65%
Androgen receptor binding	-	0.5546	55.46%
Thyroid receptor binding	+	0.6834	68.34%
Glucocorticoid receptor binding	+	0.7167	71.67%
Aromatase binding	-	0.6349	63.49%
PPAR gamma	+	0.5267	52.67%
Honey bee toxicity	-	0.8887	88.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.18%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.49%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.17%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.58%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.10%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.64%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.63%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.98%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.58%	94.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.16%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.07%	100.00%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 162960243
• LOTUS: LTS0183224
• wikiData: Q105148630