(1R,4aS,8aR)-1-[(3R)-4-Carboxy-3-methylbutyl]-5,5,8a-trimethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid

Details

• Internal ID: 48761e45-7f10-469f-a332-dba09f874b51
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aS,8aR)-1-[(3R)-4-carboxy-3-methylbutyl]-5,5,8a-trimethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalene-2-carboxylic acid
• InChI: InChI=1S/C20H30O5/c1-12(10-16(22)23)6-7-14-13(18(24)25)11-15(21)17-19(2,3)8-5-9-20(14,17)4/h11-12,14,17H,5-10H2,1-4H3,(H,22,23)(H,24,25)/t12-,14+,17+,20-/m1/s1
• InChI Key: BNEIWLJTTLILKL-SYSLWLLYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• (1R,4aS,8aR)-1-[(3R)-4-Carboxy-3-methylbutyl]-5,5,8a-trimethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid
• 108657-49-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.6332	63.32%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8385	83.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8236	82.36%
OATP1B3 inhibitior	+	0.7918	79.18%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5414	54.14%
P-glycoprotein inhibitior	-	0.6641	66.41%
P-glycoprotein substrate	-	0.6943	69.43%
CYP3A4 substrate	+	0.5511	55.11%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.6841	68.41%
CYP2C9 inhibition	-	0.9557	95.57%
CYP2C19 inhibition	-	0.9621	96.21%
CYP2D6 inhibition	-	0.9468	94.68%
CYP1A2 inhibition	-	0.9417	94.17%
CYP2C8 inhibition	-	0.8773	87.73%
CYP inhibitory promiscuity	-	0.9010	90.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7325	73.25%
Eye corrosion	-	0.9956	99.56%
Eye irritation	-	0.9012	90.12%
Skin irritation	+	0.6687	66.87%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4443	44.43%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5486	54.86%
skin sensitisation	+	0.5114	51.14%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5841	58.41%
Acute Oral Toxicity (c)	III	0.8360	83.60%
Estrogen receptor binding	+	0.6240	62.40%
Androgen receptor binding	+	0.5505	55.05%
Thyroid receptor binding	+	0.5899	58.99%
Glucocorticoid receptor binding	+	0.7710	77.10%
Aromatase binding	+	0.5200	52.00%
PPAR gamma	+	0.5566	55.66%
Honey bee toxicity	-	0.8881	88.81%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.93%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.38%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.88%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.63%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.72%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.64%	90.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.64%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.13%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.00%	97.09%

Plants that contains it

• Grindelia havardii

Cross-Links

• PubChem: 138394737
• LOTUS: LTS0241673
• wikiData: Q81983346