(2R,4aR,5R,8aS)-4a-hydroxy-2,5-dimethyl-8-propan-2-ylidene-2,3,4,5,6,8a-hexahydronaphthalene-1,7-dione

Details

• Internal ID: b0067f6a-3fbc-44c7-b4f2-85281544a29d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R,4aR,5R,8aS)-4a-hydroxy-2,5-dimethyl-8-propan-2-ylidene-2,3,4,5,6,8a-hexahydronaphthalene-1,7-dione
• SMILES (Canonical): CC1CCC2(C(CC(=O)C(=C(C)C)C2C1=O)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@@H](CC(=O)C(=C(C)C)[C@@H]2C1=O)C)O
• InChI: InChI=1S/C15H22O3/c1-8(2)12-11(16)7-10(4)15(18)6-5-9(3)14(17)13(12)15/h9-10,13,18H,5-7H2,1-4H3/t9-,10-,13-,15-/m1/s1
• InChI Key: VHUWMVDDOUSDKF-HMYIPDOQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8077	80.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8317	83.17%
OATP2B1 inhibitior	-	0.8440	84.40%
OATP1B1 inhibitior	+	0.8994	89.94%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8778	87.78%
P-glycoprotein inhibitior	-	0.9146	91.46%
P-glycoprotein substrate	-	0.8458	84.58%
CYP3A4 substrate	+	0.5264	52.64%
CYP2C9 substrate	-	0.8165	81.65%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.7190	71.90%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8613	86.13%
CYP2D6 inhibition	-	0.9618	96.18%
CYP1A2 inhibition	-	0.9343	93.43%
CYP2C8 inhibition	-	0.9434	94.34%
CYP inhibitory promiscuity	-	0.9506	95.06%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4998	49.98%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.7001	70.01%
Skin irritation	+	0.5867	58.67%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6476	64.76%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5806	58.06%
skin sensitisation	+	0.5444	54.44%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6055	60.55%
Acute Oral Toxicity (c)	I	0.5220	52.20%
Estrogen receptor binding	-	0.6087	60.87%
Androgen receptor binding	-	0.5679	56.79%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.8269	82.69%
PPAR gamma	-	0.5975	59.75%
Honey bee toxicity	-	0.8766	87.66%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	92.15%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.86%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.59%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.35%	93.04%
CHEMBL2581	P07339	Cathepsin D	87.18%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	86.12%	97.05%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.92%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.28%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.08%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.55%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.26%	94.75%

Plants that contains it

• Acorus calamus

Cross-Links

• PubChem: 163092595
• LOTUS: LTS0234455
• wikiData: Q105286628