(4S,4aR,6R,7R,8S,8aS)-7,8-dihydroxy-4,4a-dimethyl-6-prop-1-en-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one

Details

• Internal ID: f870f1b5-08a6-4f70-a4be-846dbbc3539a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: (4S,4aR,6R,7R,8S,8aS)-7,8-dihydroxy-4,4a-dimethyl-6-prop-1-en-2-yl-1,3,4,5,6,7,8,8a-octahydronaphthalen-2-one
• SMILES (Canonical): CC1CC(=O)CC2C1(CC(C(C2O)O)C(=C)C)C
• SMILES (Isomeric): C[C@H]1CC(=O)C[C@H]2[C@@]1(C[C@@H]([C@H]([C@H]2O)O)C(=C)C)C
• InChI: InChI=1S/C15H24O3/c1-8(2)11-7-15(4)9(3)5-10(16)6-12(15)14(18)13(11)17/h9,11-14,17-18H,1,5-7H2,2-4H3/t9-,11+,12+,13+,14-,15+/m0/s1
• InChI Key: YXAAITDACDFQGY-DXSVJQKISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	-	0.5559	55.59%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7619	76.19%
OATP2B1 inhibitior	-	0.8555	85.55%
OATP1B1 inhibitior	+	0.9192	91.92%
OATP1B3 inhibitior	+	0.9326	93.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9331	93.31%
P-glycoprotein inhibitior	-	0.9074	90.74%
P-glycoprotein substrate	-	0.7555	75.55%
CYP3A4 substrate	+	0.5478	54.78%
CYP2C9 substrate	-	0.8348	83.48%
CYP2D6 substrate	-	0.7829	78.29%
CYP3A4 inhibition	-	0.5295	52.95%
CYP2C9 inhibition	-	0.8511	85.11%
CYP2C19 inhibition	-	0.7616	76.16%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.8325	83.25%
CYP2C8 inhibition	-	0.9004	90.04%
CYP inhibitory promiscuity	-	0.8878	88.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5551	55.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.5744	57.44%
Skin irritation	-	0.5156	51.56%
Skin corrosion	-	0.9424	94.24%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7736	77.36%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.5469	54.69%
skin sensitisation	-	0.5457	54.57%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6316	63.16%
Acute Oral Toxicity (c)	III	0.6485	64.85%
Estrogen receptor binding	-	0.7231	72.31%
Androgen receptor binding	-	0.6383	63.83%
Thyroid receptor binding	-	0.6565	65.65%
Glucocorticoid receptor binding	-	0.5873	58.73%
Aromatase binding	-	0.6199	61.99%
PPAR gamma	-	0.8379	83.79%
Honey bee toxicity	-	0.7789	77.89%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	93.75%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.30%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.80%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.64%	85.14%
CHEMBL2581	P07339	Cathepsin D	89.38%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.10%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.40%	100.00%
CHEMBL1871	P10275	Androgen Receptor	84.98%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.66%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.09%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	80.37%	97.05%

Plants that contains it

• Euryops algoensis

Cross-Links

• PubChem: 14890372
• LOTUS: LTS0108297
• wikiData: Q105367467