2-[(2'S,4aS,6R,8S,8aS)-6-hydroxy-2',4,4,8a-tetramethyl-7-methylidenespiro[1,2,3,4a,5,6-hexahydronaphthalene-8,5'-oxolane]-2'-yl]acetic acid

Details

• Internal ID: d47f9a67-59c1-4b08-a85c-b72fa17002c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4aS,6R,8S,8aS)-6-hydroxy-2',4,4,8a-tetramethyl-7-methylidenespiro[1,2,3,4a,5,6-hexahydronaphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1(CCCC2(C1CC(C(=C)C23CCC(O3)(C)CC(=O)O)O)C)C
• SMILES (Isomeric): C[C@]1(CC[C@@]2(O1)C(=C)[C@@H](C[C@@H]3[C@@]2(CCCC3(C)C)C)O)CC(=O)O
• InChI: InChI=1S/C20H32O4/c1-13-14(21)11-15-17(2,3)7-6-8-19(15,5)20(13)10-9-18(4,24-20)12-16(22)23/h14-15,21H,1,6-12H2,2-5H3,(H,22,23)/t14-,15+,18+,19+,20-/m1/s1
• InChI Key: XOCFTIDAXQQSDD-NEILBQKWSA-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: 3.00
• 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	+	0.9866	98.66%
Caco-2	+	0.6403	64.03%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6261	62.61%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8119	81.19%
OATP1B3 inhibitior	+	0.8281	82.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.7171	71.71%
P-glycoprotein inhibitior	-	0.7796	77.96%
P-glycoprotein substrate	-	0.8629	86.29%
CYP3A4 substrate	+	0.5933	59.33%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8880	88.80%
CYP2C19 inhibition	-	0.8231	82.31%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.7535	75.35%
CYP2C8 inhibition	-	0.6026	60.26%
CYP inhibitory promiscuity	-	0.8222	82.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.7465	74.65%
Skin irritation	+	0.6749	67.49%
Skin corrosion	-	0.9217	92.17%
Ames mutagenesis	-	0.5770	57.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4642	46.42%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7246	72.46%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7651	76.51%
Acute Oral Toxicity (c)	I	0.7969	79.69%
Estrogen receptor binding	+	0.7882	78.82%
Androgen receptor binding	+	0.6425	64.25%
Thyroid receptor binding	+	0.6413	64.13%
Glucocorticoid receptor binding	+	0.6351	63.51%
Aromatase binding	+	0.7270	72.70%
PPAR gamma	+	0.5232	52.32%
Honey bee toxicity	-	0.9232	92.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9961	99.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.73%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.63%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.08%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.17%	91.07%
CHEMBL2581	P07339	Cathepsin D	83.58%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.49%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.15%	97.09%

Plants that contains it

• Ericameria paniculata
• Xanthocephalum gymnospermoides

Cross-Links

• PubChem: 102014643
• LOTUS: LTS0097248
• wikiData: Q105337688