(3aR,5aR,9aR)-3a,9a-dihydroxy-1-methyl-5,8-dimethylidene-3,4,5a,6,7,9-hexahydrocyclopenta[a]naphthalen-2-one

Details

• Internal ID: ef332d21-a8e7-4511-a9ef-bff8423952ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (3aR,5aR,9aR)-3a,9a-dihydroxy-1-methyl-5,8-dimethylidene-3,4,5a,6,7,9-hexahydrocyclopenta[a]naphthalen-2-one
• SMILES (Canonical): CC1=C2C(CC(=C)C3C2(CC(=C)CC3)O)(CC1=O)O
• SMILES (Isomeric): CC1=C2[C@@](CC(=C)[C@@H]3[C@@]2(CC(=C)CC3)O)(CC1=O)O
• InChI: InChI=1S/C16H20O3/c1-9-4-5-12-10(2)7-15(18)8-13(17)11(3)14(15)16(12,19)6-9/h12,18-19H,1-2,4-8H2,3H3/t12-,15-,16-/m1/s1
• InChI Key: SBQQRLQYMATNFJ-DAXOMENPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.33 g/mol
• Exact Mass: 260.14124450 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.6773	67.73%
Blood Brain Barrier	+	0.5527	55.27%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6541	65.41%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.9116	91.16%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5541	55.41%
BSEP inhibitior	-	0.8602	86.02%
P-glycoprotein inhibitior	-	0.9156	91.56%
P-glycoprotein substrate	-	0.8860	88.60%
CYP3A4 substrate	+	0.5706	57.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8621	86.21%
CYP3A4 inhibition	-	0.9256	92.56%
CYP2C9 inhibition	-	0.8661	86.61%
CYP2C19 inhibition	-	0.7510	75.10%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.8165	81.65%
CYP2C8 inhibition	-	0.9255	92.55%
CYP inhibitory promiscuity	-	0.8447	84.47%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4720	47.20%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.5355	53.55%
Skin irritation	+	0.5224	52.24%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5524	55.24%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.7068	70.68%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.5852	58.52%
Acute Oral Toxicity (c)	III	0.3303	33.03%
Estrogen receptor binding	+	0.5863	58.63%
Androgen receptor binding	-	0.4860	48.60%
Thyroid receptor binding	+	0.5549	55.49%
Glucocorticoid receptor binding	+	0.6707	67.07%
Aromatase binding	-	0.5422	54.22%
PPAR gamma	+	0.6185	61.85%
Honey bee toxicity	-	0.8658	86.58%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9819	98.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.14%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.70%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.24%	93.04%
CHEMBL4040	P28482	MAP kinase ERK2	85.78%	83.82%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.68%	93.03%
CHEMBL1937	Q92769	Histone deacetylase 2	85.28%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.16%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.56%	93.00%
CHEMBL1871	P10275	Androgen Receptor	81.62%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.93%	97.09%
CHEMBL2581	P07339	Cathepsin D	80.01%	98.95%

Plants that contains it

• Chloranthus multistachys

Cross-Links

• PubChem: 162905036
• LOTUS: LTS0164694
• wikiData: Q105249614