4-(3-Hydroxy-but-1-enyl)-3,5,5-trimethylcyclohex-3-ene-1,2-diol

Details

• Internal ID: 21e1f053-ae85-47ec-bc91-2c272eefb97c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 4-[(E)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol
• SMILES (Canonical): CC1=C(C(CC(C1O)O)(C)C)C=CC(C)O
• SMILES (Isomeric): CC1=C(C(CC(C1O)O)(C)C)/C=C/C(C)O
• InChI: InChI=1S/C13H22O3/c1-8(14)5-6-10-9(2)12(16)11(15)7-13(10,3)4/h5-6,8,11-12,14-16H,7H2,1-4H3/b6-5+
• InChI Key: HODWUFMHAGVDJY-AATRIKPKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.31 g/mol
• Exact Mass: 226.15689456 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.39
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 4-(3,4-Dihydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3-butene-2-ol
• 4-(3-hydroxy-but-1-enyl)-3,5,5-trimethylcyclohex-3-ene-1,2-diol
• (3E)-4-(3,4-Dihydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9868	98.68%
Caco-2	+	0.6009	60.09%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7123	71.23%
OATP2B1 inhibitior	-	0.8526	85.26%
OATP1B1 inhibitior	+	0.9175	91.75%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8254	82.54%
P-glycoprotein inhibitior	-	0.9483	94.83%
P-glycoprotein substrate	-	0.8587	85.87%
CYP3A4 substrate	-	0.5341	53.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7761	77.61%
CYP3A4 inhibition	-	0.8392	83.92%
CYP2C9 inhibition	-	0.8596	85.96%
CYP2C19 inhibition	-	0.8532	85.32%
CYP2D6 inhibition	-	0.9434	94.34%
CYP1A2 inhibition	-	0.9154	91.54%
CYP2C8 inhibition	-	0.9373	93.73%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5199	51.99%
Eye corrosion	-	0.9695	96.95%
Eye irritation	-	0.8579	85.79%
Skin irritation	-	0.6100	61.00%
Skin corrosion	-	0.8806	88.06%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5781	57.81%
Micronuclear	-	0.7668	76.68%
Hepatotoxicity	-	0.6177	61.77%
skin sensitisation	+	0.7901	79.01%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	III	0.7455	74.55%
Estrogen receptor binding	-	0.9136	91.36%
Androgen receptor binding	-	0.8004	80.04%
Thyroid receptor binding	-	0.4875	48.75%
Glucocorticoid receptor binding	-	0.8091	80.91%
Aromatase binding	-	0.8675	86.75%
PPAR gamma	-	0.8215	82.15%
Honey bee toxicity	-	0.8347	83.47%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8330	83.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.47%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.80%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.48%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.40%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	88.06%	95.58%
CHEMBL221	P23219	Cyclooxygenase-1	87.79%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.48%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.34%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	84.35%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.22%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.06%	95.89%

Plants that contains it

• Crocus sativus

Cross-Links

• PubChem: 15628171
• NPASS: NPC107151