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

Details

• Internal ID: 7d985c09-b3ec-4482-b58c-4b795ce984ad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4aS,8S,8aS)-7-(hydroxymethyl)-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)CO)C)C
• SMILES (Isomeric): C[C@]1(CC[C@@]2(O1)C(=CC[C@@H]3[C@@]2(CCCC3(C)C)C)CO)CC(=O)O
• InChI: InChI=1S/C20H32O4/c1-17(2)8-5-9-19(4)15(17)7-6-14(13-21)20(19)11-10-18(3,24-20)12-16(22)23/h6,15,21H,5,7-13H2,1-4H3,(H,22,23)/t15-,18-,19-,20+/m0/s1
• InChI Key: RBVRYDWTKMWSNY-MVJPYGJCSA-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: 2.80
• 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	+	0.9843	98.43%
Caco-2	+	0.7462	74.62%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6639	66.39%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8262	82.62%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5317	53.17%
BSEP inhibitior	-	0.6324	63.24%
P-glycoprotein inhibitior	-	0.8417	84.17%
P-glycoprotein substrate	-	0.8859	88.59%
CYP3A4 substrate	+	0.5681	56.81%
CYP2C9 substrate	-	0.6145	61.45%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	-	0.6684	66.84%
CYP2C9 inhibition	-	0.7982	79.82%
CYP2C19 inhibition	-	0.8469	84.69%
CYP2D6 inhibition	-	0.9034	90.34%
CYP1A2 inhibition	-	0.8102	81.02%
CYP2C8 inhibition	-	0.6070	60.70%
CYP inhibitory promiscuity	-	0.7326	73.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5450	54.50%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.8426	84.26%
Skin irritation	-	0.6066	60.66%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6445	64.45%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.7713	77.13%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8149	81.49%
Acute Oral Toxicity (c)	III	0.6429	64.29%
Estrogen receptor binding	+	0.7569	75.69%
Androgen receptor binding	+	0.6127	61.27%
Thyroid receptor binding	+	0.6881	68.81%
Glucocorticoid receptor binding	+	0.6285	62.85%
Aromatase binding	+	0.7154	71.54%
PPAR gamma	+	0.5416	54.16%
Honey bee toxicity	-	0.9400	94.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9734	97.34%

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	96.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.38%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.82%	97.25%
CHEMBL2581	P07339	Cathepsin D	88.78%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	83.52%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.07%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.76%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.14%	97.09%

Plants that contains it

• Chrysoma pauciflosculosa
• Grindelia hirsutula
• Isocoma tenuisecta
• Xanthocephalum gymnospermoides

Cross-Links

• PubChem: 102014644
• LOTUS: LTS0254854
• wikiData: Q105233375