(4aR,5R,8R,8aR)-8-[(1S)-1-carboxyethyl]-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid

Details

• Internal ID: ba0ab740-d31e-4e82-8d3c-d0dccc546ab9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4aR,5R,8R,8aR)-8-[(1S)-1-carboxyethyl]-5-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)C(=O)O)C(C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@H]2[C@@H]1CCC(=C2)C(=O)O)[C@H](C)C(=O)O
• InChI: InChI=1S/C15H22O4/c1-8-3-5-12(9(2)14(16)17)13-7-10(15(18)19)4-6-11(8)13/h7-9,11-13H,3-6H2,1-2H3,(H,16,17)(H,18,19)/t8-,9+,11-,12+,13-/m1/s1
• InChI Key: KRUUDBOQHFKKKU-XUEURGHRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	+	0.6937	69.37%
Blood Brain Barrier	+	0.5605	56.05%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7236	72.36%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9043	90.43%
OATP1B3 inhibitior	+	0.8136	81.36%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	-	0.9450	94.50%
P-glycoprotein inhibitior	-	0.9547	95.47%
P-glycoprotein substrate	-	0.8743	87.43%
CYP3A4 substrate	-	0.5479	54.79%
CYP2C9 substrate	-	0.5618	56.18%
CYP2D6 substrate	-	0.9140	91.40%
CYP3A4 inhibition	-	0.8426	84.26%
CYP2C9 inhibition	-	0.8817	88.17%
CYP2C19 inhibition	-	0.9235	92.35%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.7129	71.29%
CYP2C8 inhibition	-	0.9257	92.57%
CYP inhibitory promiscuity	-	0.9138	91.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6502	65.02%
Eye corrosion	-	0.9596	95.96%
Eye irritation	-	0.7068	70.68%
Skin irritation	-	0.7850	78.50%
Skin corrosion	-	0.9787	97.87%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6725	67.25%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	+	0.7251	72.51%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5521	55.21%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8372	83.72%
Acute Oral Toxicity (c)	III	0.6537	65.37%
Estrogen receptor binding	-	0.7312	73.12%
Androgen receptor binding	+	0.6295	62.95%
Thyroid receptor binding	-	0.6506	65.06%
Glucocorticoid receptor binding	-	0.5294	52.94%
Aromatase binding	-	0.8951	89.51%
PPAR gamma	-	0.7134	71.34%
Honey bee toxicity	-	0.9457	94.57%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	97.54%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.83%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.99%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.85%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.55%	93.00%

Plants that contains it

• Eremophila mitchellii

Cross-Links

• PubChem: 163007664
• LOTUS: LTS0224807
• wikiData: Q105145250