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

Details

• Internal ID: 61d8038a-900e-47b4-8fce-488a75a03b3c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4aS,5R,8R,8aS)-5-hydroxy-2',4,4,7,8a-pentamethylspiro[2,3,4a,5-tetrahydro-1H-naphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CC(C2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)C)O
• SMILES (Isomeric): CC1=C[C@H]([C@@H]2[C@@]([C@@]13CC[C@@](O3)(C)CC(=O)O)(CCCC2(C)C)C)O
• InChI: InChI=1S/C20H32O4/c1-13-11-14(21)16-17(2,3)7-6-8-19(16,5)20(13)10-9-18(4,24-20)12-15(22)23/h11,14,16,21H,6-10,12H2,1-5H3,(H,22,23)/t14-,16+,18+,19+,20-/m1/s1
• InChI Key: OCBYZNFGCPOXBL-YANNOABASA-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	+	0.9897	98.97%
Caco-2	+	0.7096	70.96%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6513	65.13%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.7833	78.33%
OATP1B3 inhibitior	+	0.9309	93.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8123	81.23%
P-glycoprotein substrate	-	0.8493	84.93%
CYP3A4 substrate	+	0.5713	57.13%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	-	0.8355	83.55%
CYP3A4 inhibition	-	0.6470	64.70%
CYP2C9 inhibition	-	0.8768	87.68%
CYP2C19 inhibition	-	0.8252	82.52%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.8009	80.09%
CYP2C8 inhibition	-	0.7143	71.43%
CYP inhibitory promiscuity	-	0.8205	82.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5301	53.01%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8728	87.28%
Skin irritation	+	0.5997	59.97%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4868	48.68%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.7181	71.81%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7382	73.82%
Acute Oral Toxicity (c)	I	0.6342	63.42%
Estrogen receptor binding	+	0.7708	77.08%
Androgen receptor binding	+	0.6078	60.78%
Thyroid receptor binding	+	0.7316	73.16%
Glucocorticoid receptor binding	+	0.6595	65.95%
Aromatase binding	+	0.7716	77.16%
PPAR gamma	+	0.5927	59.27%
Honey bee toxicity	-	0.9477	94.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9862	98.62%

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	93.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.08%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.50%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	86.33%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.25%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.87%	86.00%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 102060451
• LOTUS: LTS0157397
• wikiData: Q105189278