(2S)-2-[(1aR,3aS,4R,7R,7aS,7bS)-1a,4-dimethyl-3,3a,4,5,6,7,7a,7b-octahydro-2H-naphtho[1,2-b]oxiren-7-yl]propanoic acid

Details

• Internal ID: cd6eef61-4a72-4f35-b497-2683ba3c618b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2S)-2-[(1aR,3aS,4R,7R,7aS,7bS)-1a,4-dimethyl-3,3a,4,5,6,7,7a,7b-octahydro-2H-naphtho[1,2-b]oxiren-7-yl]propanoic acid
• SMILES (Canonical): CC1CCC(C2C1CCC3(C2O3)C)C(C)C(=O)O
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@@H]2[C@H]1CC[C@@]3([C@H]2O3)C)[C@H](C)C(=O)O
• InChI: InChI=1S/C15H24O3/c1-8-4-5-11(9(2)14(16)17)12-10(8)6-7-15(3)13(12)18-15/h8-13H,4-7H2,1-3H3,(H,16,17)/t8-,9+,10+,11+,12+,13+,15-/m1/s1
• InChI Key: FRUVDMZCZGVCDC-ASBIXWSPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9814	98.14%
Caco-2	+	0.7825	78.25%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4814	48.14%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9341	93.41%
P-glycoprotein inhibitior	-	0.9172	91.72%
P-glycoprotein substrate	-	0.8567	85.67%
CYP3A4 substrate	+	0.5559	55.59%
CYP2C9 substrate	+	0.6276	62.76%
CYP2D6 substrate	-	0.8576	85.76%
CYP3A4 inhibition	-	0.8542	85.42%
CYP2C9 inhibition	-	0.5799	57.99%
CYP2C19 inhibition	-	0.7386	73.86%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.5767	57.67%
CYP2C8 inhibition	-	0.8615	86.15%
CYP inhibitory promiscuity	-	0.9609	96.09%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6910	69.10%
Eye corrosion	-	0.9649	96.49%
Eye irritation	-	0.8513	85.13%
Skin irritation	-	0.6020	60.20%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.7253	72.53%
Human Ether-a-go-go-Related Gene inhibition	-	0.6818	68.18%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.6412	64.12%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.5734	57.34%
Acute Oral Toxicity (c)	III	0.6874	68.74%
Estrogen receptor binding	-	0.5752	57.52%
Androgen receptor binding	+	0.6331	63.31%
Thyroid receptor binding	+	0.6722	67.22%
Glucocorticoid receptor binding	+	0.6452	64.52%
Aromatase binding	-	0.6380	63.80%
PPAR gamma	-	0.5319	53.19%
Honey bee toxicity	-	0.8559	85.59%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9448	94.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.76%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.75%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.55%	96.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.13%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	82.81%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	81.93%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.79%	95.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.49%	93.04%
CHEMBL5028	O14672	ADAM10	81.39%	97.50%

Plants that contains it

• Artemisia annua

Cross-Links

• PubChem: 154497729
• LOTUS: LTS0111222
• wikiData: Q105000452