(2R,5S)-4,4'aalpha,5,5',6',7',8',8'a-Octahydro-5'alpha-(hydroxymethyl)-2',5,5',8'abeta-tetramethyl-4'-oxospiro[furan-2(3H),1'(4'H)-naphthalene]-5-acetic acid

Details

• Internal ID: 97e26965-8ae9-429a-b0af-ebb532d83c19
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(2'S,4R,4aS,8R,8aS)-4-(hydroxymethyl)-2',4,7,8a-tetramethyl-5-oxospiro[1,2,3,4a-tetrahydronaphthalene-8,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1=CC(=O)C2C(CCCC2(C13CCC(O3)(C)CC(=O)O)C)(C)CO
• SMILES (Isomeric): CC1=CC(=O)[C@H]2[C@](CCC[C@@]2([C@@]13CC[C@@](O3)(C)CC(=O)O)C)(C)CO
• InChI: InChI=1S/C20H30O5/c1-13-10-14(22)16-17(2,12-21)6-5-7-19(16,4)20(13)9-8-18(3,25-20)11-15(23)24/h10,16,21H,5-9,11-12H2,1-4H3,(H,23,24)/t16-,17-,18-,19-,20+/m0/s1
• InChI Key: YKJKZQHYTCDZKN-VYJAJWGXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.20932405 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 4
• 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	+	0.9874	98.74%
Caco-2	+	0.7369	73.69%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7798	77.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7532	75.32%
OATP1B3 inhibitior	+	0.9521	95.21%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5621	56.21%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7977	79.77%
P-glycoprotein substrate	-	0.8239	82.39%
CYP3A4 substrate	+	0.5869	58.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9007	90.07%
CYP3A4 inhibition	+	0.5169	51.69%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.9347	93.47%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.8709	87.09%
CYP2C8 inhibition	-	0.6987	69.87%
CYP inhibitory promiscuity	-	0.9030	90.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5153	51.53%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8077	80.77%
Skin irritation	+	0.5574	55.74%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3822	38.22%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.9019	90.19%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7893	78.93%
Acute Oral Toxicity (c)	III	0.5406	54.06%
Estrogen receptor binding	+	0.8179	81.79%
Androgen receptor binding	+	0.6844	68.44%
Thyroid receptor binding	+	0.6916	69.16%
Glucocorticoid receptor binding	+	0.6633	66.33%
Aromatase binding	+	0.7417	74.17%
PPAR gamma	+	0.5454	54.54%
Honey bee toxicity	-	0.9499	94.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9768	97.68%

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	94.93%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.29%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.82%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.81%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.00%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	83.25%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.23%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.38%	85.14%

Plants that contains it

• Grindelia hirsutula

Cross-Links

• PubChem: 10498058
• LOTUS: LTS0111418
• wikiData: Q105349723