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

Details

• Internal ID: d1a1871c-0b20-4058-8b75-275c2f8666c4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4S,4aR,8R,8aS)-4-(hydroxymethyl)-2',4,7,8a-tetramethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CCC2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)CO
• SMILES (Isomeric): CC1=CC[C@@H]2[C@@](CCC[C@@]2([C@@]13CC[C@@](O3)(C)CC(=O)O)C)(C)CO
• InChI: InChI=1S/C20H32O4/c1-14-6-7-15-17(2,13-21)8-5-9-19(15,4)20(14)11-10-18(3,24-20)12-16(22)23/h6,15,21H,5,7-13H2,1-4H3,(H,22,23)/t15-,17-,18+,19+,20-/m1/s1
• InChI Key: DJSOIWVYQLXAFK-LFZDHENXSA-N
• Popularity: 1 reference 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: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9883	98.83%
Caco-2	+	0.7342	73.42%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6659	66.59%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.7915	79.15%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5669	56.69%
BSEP inhibitior	+	0.5911	59.11%
P-glycoprotein inhibitior	-	0.8587	85.87%
P-glycoprotein substrate	-	0.8746	87.46%
CYP3A4 substrate	+	0.5702	57.02%
CYP2C9 substrate	-	0.6145	61.45%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	-	0.5341	53.41%
CYP2C9 inhibition	-	0.8245	82.45%
CYP2C19 inhibition	-	0.8780	87.80%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.8269	82.69%
CYP2C8 inhibition	-	0.6224	62.24%
CYP inhibitory promiscuity	-	0.7774	77.74%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5666	56.66%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7711	77.11%
Skin irritation	-	0.6134	61.34%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.7191	71.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.4048	40.48%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8448	84.48%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8405	84.05%
Acute Oral Toxicity (c)	III	0.5767	57.67%
Estrogen receptor binding	+	0.7565	75.65%
Androgen receptor binding	+	0.6389	63.89%
Thyroid receptor binding	+	0.6544	65.44%
Glucocorticoid receptor binding	+	0.5623	56.23%
Aromatase binding	+	0.7628	76.28%
PPAR gamma	-	0.5141	51.41%
Honey bee toxicity	-	0.9463	94.63%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9709	97.09%

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	92.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.98%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.90%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	86.64%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.97%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.62%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	80.28%	91.19%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 163053783
• LOTUS: LTS0206411
• wikiData: Q104982756