(3R,3aR,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,8-tetrahydroazulene-4,7-dione

Details

• Internal ID: 22f3e57d-e3a9-4692-8265-314f5c92e2cd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (3R,3aR,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,8-tetrahydroazulene-4,7-dione
• SMILES (Canonical): CC1=CC(=O)C2C(CCC2(C(C)C)O)(CC1=O)C
• SMILES (Isomeric): CC1=CC(=O)[C@@H]2[C@](CC[C@]2(C(C)C)O)(CC1=O)C
• InChI: InChI=1S/C15H22O3/c1-9(2)15(18)6-5-14(4)8-12(17)10(3)7-11(16)13(14)15/h7,9,13,18H,5-6,8H2,1-4H3/t13-,14-,15-/m1/s1
• InChI Key: ZXKNFFWIVMCXAG-RBSFLKMASA-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: 1.80
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.8216	82.16%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7189	71.89%
OATP2B1 inhibitior	-	0.8495	84.95%
OATP1B1 inhibitior	+	0.9131	91.31%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8896	88.96%
P-glycoprotein inhibitior	-	0.9065	90.65%
P-glycoprotein substrate	-	0.8209	82.09%
CYP3A4 substrate	+	0.5291	52.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8953	89.53%
CYP3A4 inhibition	-	0.8520	85.20%
CYP2C9 inhibition	-	0.6549	65.49%
CYP2C19 inhibition	-	0.7290	72.90%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.7506	75.06%
CYP2C8 inhibition	-	0.9720	97.20%
CYP inhibitory promiscuity	-	0.9492	94.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5168	51.68%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.6409	64.09%
Skin irritation	+	0.6481	64.81%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4329	43.29%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5969	59.69%
skin sensitisation	-	0.6027	60.27%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.7799	77.99%
Acute Oral Toxicity (c)	II	0.4646	46.46%
Estrogen receptor binding	-	0.7485	74.85%
Androgen receptor binding	-	0.4843	48.43%
Thyroid receptor binding	+	0.5137	51.37%
Glucocorticoid receptor binding	-	0.8091	80.91%
Aromatase binding	-	0.7814	78.14%
PPAR gamma	-	0.5629	56.29%
Honey bee toxicity	-	0.9233	92.33%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9805	98.05%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.70%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.49%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	91.87%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.41%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.59%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.25%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.93%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.10%	93.99%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.58%	94.78%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.70%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.09%	97.09%

Plants that contains it

• Ferula hermonis

Cross-Links

• PubChem: 11207454
• LOTUS: LTS0142041
• wikiData: Q105385586