3-Hydroxy-beta-damascone

Details

• Internal ID: d389a74e-67c1-40ea-9e90-50ce7c41cbf6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Alpha,beta-unsaturated ketones > Enones
• IUPAC Name: (E)-1-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-2-en-1-one
• SMILES (Canonical): CC=CC(=O)C1=C(C(CCC1(C)C)O)C
• SMILES (Isomeric): C/C=C/C(=O)C1=C(C(CCC1(C)C)O)C
• InChI: InChI=1S/C13H20O2/c1-5-6-11(15)12-9(2)10(14)7-8-13(12,3)4/h5-6,10,14H,7-8H2,1-4H3/b6-5+
• InChI Key: NOORESDHJXLGAO-AATRIKPKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.30 g/mol
• Exact Mass: 208.146329876 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• NOORESDHJXLGAO-AATRIKPKSA-N
• 4-Hydroxy-5,8-megastigmadien-7-one
• (2E)-1-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
• (2E)-1-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8268	82.68%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7175	71.75%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.8888	88.88%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8653	86.53%
P-glycoprotein inhibitior	-	0.9834	98.34%
P-glycoprotein substrate	-	0.9307	93.07%
CYP3A4 substrate	+	0.5159	51.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.8382	83.82%
CYP2C9 inhibition	-	0.9101	91.01%
CYP2C19 inhibition	-	0.9114	91.14%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.8802	88.02%
CYP2C8 inhibition	-	0.8471	84.71%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8328	83.28%
Carcinogenicity (trinary)	Non-required	0.5677	56.77%
Eye corrosion	-	0.9696	96.96%
Eye irritation	-	0.7342	73.42%
Skin irritation	+	0.8041	80.41%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5682	56.82%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	+	0.8845	88.45%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.7465	74.65%
Acute Oral Toxicity (c)	III	0.8329	83.29%
Estrogen receptor binding	-	0.9787	97.87%
Androgen receptor binding	-	0.8213	82.13%
Thyroid receptor binding	-	0.6918	69.18%
Glucocorticoid receptor binding	-	0.9139	91.39%
Aromatase binding	-	0.9495	94.95%
PPAR gamma	-	0.8190	81.90%
Honey bee toxicity	-	0.8915	89.15%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8451	84.51%

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	93.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.11%	94.45%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.06%	97.47%
CHEMBL221	P23219	Cyclooxygenase-1	82.96%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	81.37%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.37%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.25%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.16%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.17%	100.00%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 5366075
• NPASS: NPC155312