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

Details

• Internal ID: 3c86b1eb-08f9-49f9-8b94-c82a790bd552
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl 2-[(2'S,3S,4aS,8R,8aS)-3-hydroxy-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetate
• SMILES (Canonical): CC1=CCC2C(C(CCC2(C13CCC(O3)(C)CC(=O)OC)C)O)(C)C
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CC(=O)OC)(CC[C@@H](C2(C)C)O)C
• InChI: InChI=1S/C21H34O4/c1-14-7-8-15-18(2,3)16(22)9-10-20(15,5)21(14)12-11-19(4,25-21)13-17(23)24-6/h7,15-16,22H,8-13H2,1-6H3/t15-,16-,19-,20-,21+/m0/s1
• InChI Key: HKWVZPQQUZNBOF-JPKZGUTDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.50 g/mol
• Exact Mass: 350.24570956 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.01
• H-Bond Acceptor: 4
• 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	+	0.9927	99.27%
Caco-2	+	0.7592	75.92%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7461	74.61%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.8515	85.15%
OATP1B3 inhibitior	+	0.8032	80.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6090	60.90%
P-glycoprotein inhibitior	-	0.7395	73.95%
P-glycoprotein substrate	-	0.8354	83.54%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8380	83.80%
CYP3A4 inhibition	-	0.5086	50.86%
CYP2C9 inhibition	-	0.6101	61.01%
CYP2C19 inhibition	-	0.6911	69.11%
CYP2D6 inhibition	-	0.9480	94.80%
CYP1A2 inhibition	-	0.7383	73.83%
CYP2C8 inhibition	-	0.5898	58.98%
CYP inhibitory promiscuity	-	0.7797	77.97%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6084	60.84%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8956	89.56%
Skin irritation	+	0.5111	51.11%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.7169	71.69%
Human Ether-a-go-go-Related Gene inhibition	+	0.6655	66.55%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7215	72.15%
skin sensitisation	-	0.8010	80.10%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7222	72.22%
Acute Oral Toxicity (c)	I	0.5194	51.94%
Estrogen receptor binding	+	0.6349	63.49%
Androgen receptor binding	+	0.5957	59.57%
Thyroid receptor binding	+	0.7775	77.75%
Glucocorticoid receptor binding	+	0.6777	67.77%
Aromatase binding	+	0.7920	79.20%
PPAR gamma	+	0.5956	59.56%
Honey bee toxicity	-	0.8915	89.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9879	98.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.06%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	94.92%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.89%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.75%	96.95%
CHEMBL1871	P10275	Androgen Receptor	85.71%	96.43%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.56%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.50%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.14%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.67%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.63%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.57%	100.00%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 14138798
• LOTUS: LTS0134866
• wikiData: Q105030004