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

Details

• Internal ID: ddf39412-10c5-4fff-8fe3-1cf6a32deb52
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'R,3S,4aR,8R,8aS)-3-hydroxy-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CCC2C(C(CCC2(C13CCC(O3)(C)CC(=O)O)C)O)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@@]13CC[C@](O3)(C)CC(=O)O)(CC[C@@H](C2(C)C)O)C
• InChI: InChI=1S/C20H32O4/c1-13-6-7-14-17(2,3)15(21)8-9-19(14,5)20(13)11-10-18(4,24-20)12-16(22)23/h6,14-15,21H,7-12H2,1-5H3,(H,22,23)/t14-,15+,18-,19+,20-/m1/s1
• InChI Key: NRFUGXICRLTIFH-RNEXODBNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.7201	72.01%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7384	73.84%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8594	85.94%
OATP1B3 inhibitior	+	0.8823	88.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5192	51.92%
P-glycoprotein inhibitior	-	0.8607	86.07%
P-glycoprotein substrate	-	0.9069	90.69%
CYP3A4 substrate	+	0.5875	58.75%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.5333	53.33%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.9568	95.68%
CYP1A2 inhibition	-	0.8322	83.22%
CYP2C8 inhibition	-	0.6811	68.11%
CYP inhibitory promiscuity	-	0.8152	81.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5515	55.15%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8618	86.18%
Skin irritation	+	0.6504	65.04%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	-	0.7737	77.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5389	53.89%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7386	73.86%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8304	83.04%
Acute Oral Toxicity (c)	I	0.8055	80.55%
Estrogen receptor binding	+	0.6074	60.74%
Androgen receptor binding	+	0.5784	57.84%
Thyroid receptor binding	+	0.7079	70.79%
Glucocorticoid receptor binding	+	0.5864	58.64%
Aromatase binding	+	0.7254	72.54%
PPAR gamma	-	0.4848	48.48%
Honey bee toxicity	-	0.9451	94.51%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9932	99.32%

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	92.93%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.72%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.86%	91.11%
CHEMBL2581	P07339	Cathepsin D	86.82%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.43%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.71%	100.00%
CHEMBL1871	P10275	Androgen Receptor	82.51%	96.43%

Plants that contains it

• Grindelia integrifolia

Cross-Links

• PubChem: 163023591
• LOTUS: LTS0222419
• wikiData: Q105184514