Guaiol acetate

Details

• Internal ID: bf996c1c-d0b0-441e-9e73-34293c94a673
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-yl acetate
• SMILES (Canonical): CC1CCC(CC2=C1CCC2C)C(C)(C)OC(=O)C
• SMILES (Isomeric): C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(C)(C)OC(=O)C
• InChI: InChI=1S/C17H28O2/c1-11-6-8-14(17(4,5)19-13(3)18)10-16-12(2)7-9-15(11)16/h11-12,14H,6-10H2,1-5H3/t11-,12-,14+/m0/s1
• InChI Key: DRFSOBZVMGLICQ-SGMGOOAPSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₈O₂
• Molecular Weight: 264.40 g/mol
• Exact Mass: 264.208930132 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.49
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Guaiac acetate
• Guaiyl acetate
• 134-28-1
• Guaiol, acetate
• Guaiac wood acetate
• UNII-4J2P61VYV9
• 4J2P61VYV9
• NSC46160
• NSC-46160
• Octahydroazulene acetate
• Guai-1(5)-en-11-ol, acetate
• Guai-1-en-11-ol acetate
• EINECS 205-135-0
• NSC 46160
• 1,4-Dimethyl-7-(alpha-hydroxyisopropyl)-delta9,10-octahydroazule
• 1-Methyl-1-((3S,8S)-1,2,3,4,5,6,7,8-octahydro-3,8-dimethylazulen-5-yl)ethyl acetate
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, acetate, (3S,5R,8S)-
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha-3,8-tetramethyl-, acetate, (3S-(3alpha,5alpha,8alpha))-
• 5-Azulenemethanol, 1,2,3,4,5alpha,6,7,8-octahydro-alpha,alpha,3beta,8beta-tetramethyl-, acetate
• GUAIYL ACETATE [FHFI]
• SCHEMBL1666524
• DTXSID7051684
• CHEBI:173881
• 1 - methyl - 1 - ((3S,8S) - 1,2,3,4,5,6,7,8 - octahydro - 3,8 - dimethylazulen - 5 - yl)ethyl acetate
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro- ?,?,3,8-tetramethyl-, acetate, [3S-(3?,5?,8?)]-
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, acetate, (3S,5R,8S)-
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, acetate, (3S-(3alpha,5alpha,8alpha))-
• 5-Azulenemethanol, 1,2,3,4,5.alpha.,6,7,8-octahydro-.alpha.,.alpha.,3.beta.,8.beta.-tetramethyl-, acetate
• 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-yl acetate
• Q27259699
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, 5-acetate, (3S,5R,8S)-
• 5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, 5-acetate, (3S,5R,8S)-
• 5-Azulenemethanol,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, acetate, [3S-(3.alpha.,5.alpha.,8.alpha.)]-
• 5-Azulenemethanol,2,3,4,5.alpha.,6,7,8-octahydro-.alpha.,.alpha.,3.beta.,8.beta.-tetramethyl-, acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.7469	74.69%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4570	45.70%
OATP2B1 inhibitior	-	0.8505	85.05%
OATP1B1 inhibitior	+	0.9388	93.88%
OATP1B3 inhibitior	+	0.9024	90.24%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7453	74.53%
P-glycoprotein inhibitior	-	0.6410	64.10%
P-glycoprotein substrate	-	0.8937	89.37%
CYP3A4 substrate	+	0.5120	51.20%
CYP2C9 substrate	+	0.5963	59.63%
CYP2D6 substrate	-	0.8518	85.18%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.5664	56.64%
CYP2C19 inhibition	+	0.5934	59.34%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.6805	68.05%
CYP2C8 inhibition	-	0.8741	87.41%
CYP inhibitory promiscuity	-	0.8050	80.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7500	75.00%
Carcinogenicity (trinary)	Non-required	0.5084	50.84%
Eye corrosion	-	0.9395	93.95%
Eye irritation	+	0.6153	61.53%
Skin irritation	-	0.5161	51.61%
Skin corrosion	-	0.9873	98.73%
Ames mutagenesis	-	0.8354	83.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4191	41.91%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.7151	71.51%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	0.6778	67.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6476	64.76%
Acute Oral Toxicity (c)	III	0.8280	82.80%
Estrogen receptor binding	-	0.4836	48.36%
Androgen receptor binding	-	0.6285	62.85%
Thyroid receptor binding	-	0.5132	51.32%
Glucocorticoid receptor binding	-	0.6257	62.57%
Aromatase binding	-	0.6620	66.20%
PPAR gamma	-	0.7083	70.83%
Honey bee toxicity	-	0.8946	89.46%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9929	99.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.57%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.94%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.12%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.09%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	81.90%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.64%	97.09%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis

Cross-Links

• PubChem: 240122
• NPASS: NPC236564
• LOTUS: LTS0131671
• wikiData: Q27259699