2-[(2'S,4aS,8S,8aS)-7-methoxycarbonyl-2',4,4,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid

Details

• Internal ID: f351e497-5a36-464b-b962-8d9d4c91ecb5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4aS,8S,8aS)-7-methoxycarbonyl-2',4,4,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1(CCCC2(C1CC=C(C23CCC(O3)(C)CC(=O)O)C(=O)OC)C)C
• SMILES (Isomeric): C[C@]1(CC[C@@]2(O1)C(=CC[C@@H]3[C@@]2(CCCC3(C)C)C)C(=O)OC)CC(=O)O
• InChI: InChI=1S/C21H32O5/c1-18(2)9-6-10-20(4)15(18)8-7-14(17(24)25-5)21(20)12-11-19(3,26-21)13-16(22)23/h7,15H,6,8-13H2,1-5H3,(H,22,23)/t15-,19-,20-,21+/m0/s1
• InChI Key: BWADDJDJLUBKIC-FCRQHZQGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.50 g/mol
• Exact Mass: 364.22497412 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 4.10
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.7483	74.83%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6978	69.78%
OATP2B1 inhibitior	-	0.8651	86.51%
OATP1B1 inhibitior	+	0.8139	81.39%
OATP1B3 inhibitior	+	0.8809	88.09%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6603	66.03%
P-glycoprotein substrate	-	0.8468	84.68%
CYP3A4 substrate	+	0.6143	61.43%
CYP2C9 substrate	-	0.8149	81.49%
CYP2D6 substrate	-	0.9084	90.84%
CYP3A4 inhibition	-	0.6270	62.70%
CYP2C9 inhibition	-	0.6713	67.13%
CYP2C19 inhibition	-	0.7812	78.12%
CYP2D6 inhibition	-	0.9238	92.38%
CYP1A2 inhibition	-	0.7408	74.08%
CYP2C8 inhibition	+	0.5379	53.79%
CYP inhibitory promiscuity	-	0.7697	76.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6242	62.42%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.8568	85.68%
Skin irritation	-	0.6240	62.40%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6568	65.68%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5466	54.66%
skin sensitisation	-	0.7383	73.83%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7285	72.85%
Acute Oral Toxicity (c)	III	0.4165	41.65%
Estrogen receptor binding	+	0.8429	84.29%
Androgen receptor binding	+	0.6219	62.19%
Thyroid receptor binding	+	0.7405	74.05%
Glucocorticoid receptor binding	+	0.6373	63.73%
Aromatase binding	+	0.7353	73.53%
PPAR gamma	+	0.7617	76.17%
Honey bee toxicity	-	0.9151	91.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9855	98.55%

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	97.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.83%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.88%	90.17%
CHEMBL2581	P07339	Cathepsin D	89.08%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.33%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.57%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.46%	91.07%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.84%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.20%	91.19%
CHEMBL5028	O14672	ADAM10	81.99%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	80.36%	83.82%

Plants that contains it

• Chrysoma pauciflosculosa

Cross-Links

• PubChem: 162923531
• LOTUS: LTS0111309
• wikiData: Q104947044