2-[(3S,3aS,5R,8S,8aS)-3-acetyloxy-3a,8-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-azulen-5-yl]prop-2-enoic acid

Details

• Internal ID: 9b5664bb-edb5-4225-af4d-470e1b12c6b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Pseudoguaianes
• IUPAC Name: 2-[(3S,3aS,5R,8S,8aS)-3-acetyloxy-3a,8-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-azulen-5-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(CC2(C1CCC2OC(=O)C)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H]1CC[C@H](C[C@]2([C@H]1CC[C@@H]2OC(=O)C)C)C(=C)C(=O)O
• InChI: InChI=1S/C17H26O4/c1-10-5-6-13(11(2)16(19)20)9-17(4)14(10)7-8-15(17)21-12(3)18/h10,13-15H,2,5-9H2,1,3-4H3,(H,19,20)/t10-,13+,14-,15-,17-/m0/s1
• InChI Key: JSANAILUYYDJOG-DPJWHCEJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9751	97.51%
Caco-2	+	0.8775	87.75%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7221	72.21%
OATP2B1 inhibitior	-	0.8558	85.58%
OATP1B1 inhibitior	+	0.9180	91.80%
OATP1B3 inhibitior	+	0.8267	82.67%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.7745	77.45%
P-glycoprotein inhibitior	-	0.7291	72.91%
P-glycoprotein substrate	-	0.8793	87.93%
CYP3A4 substrate	+	0.6478	64.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	-	0.7800	78.00%
CYP2C9 inhibition	-	0.8073	80.73%
CYP2C19 inhibition	-	0.8727	87.27%
CYP2D6 inhibition	-	0.9417	94.17%
CYP1A2 inhibition	+	0.6350	63.50%
CYP2C8 inhibition	-	0.5945	59.45%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6530	65.30%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.7512	75.12%
Skin irritation	+	0.6443	64.43%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4197	41.97%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6948	69.48%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5205	52.05%
Acute Oral Toxicity (c)	III	0.5083	50.83%
Estrogen receptor binding	+	0.8370	83.70%
Androgen receptor binding	-	0.4842	48.42%
Thyroid receptor binding	-	0.5603	56.03%
Glucocorticoid receptor binding	+	0.6107	61.07%
Aromatase binding	+	0.5964	59.64%
PPAR gamma	+	0.5752	57.52%
Honey bee toxicity	-	0.7486	74.86%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5645	56.45%
Fish aquatic toxicity	+	0.9964	99.64%

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	97.17%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	93.51%	83.82%
CHEMBL340	P08684	Cytochrome P450 3A4	91.32%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.07%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.41%	92.94%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.14%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.56%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.40%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	80.29%	92.50%

Plants that contains it

• Calea sickii

Cross-Links

• PubChem: 162888800
• LOTUS: LTS0003363
• wikiData: Q105134226