2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]prop-2-enoic acid

Details

• Internal ID: 01ef3be8-25ee-49c6-b58f-7c04807a6e7f
• 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]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(CC2=C1CCC2C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O2/c1-9-4-6-12(11(3)15(16)17)8-14-10(2)5-7-13(9)14/h9-10,12H,3-8H2,1-2H3,(H,16,17)/t9-,10-,12+/m0/s1
• InChI Key: XIOGSACNJBIHRS-JBLDHEPKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.9195	91.95%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Lysosomes	0.3632	36.32%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.9318	93.18%
OATP1B3 inhibitior	+	0.8856	88.56%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.8857	88.57%
P-glycoprotein inhibitior	-	0.8864	88.64%
P-glycoprotein substrate	-	0.9293	92.93%
CYP3A4 substrate	-	0.5657	56.57%
CYP2C9 substrate	+	0.6092	60.92%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.9336	93.36%
CYP2C9 inhibition	-	0.7139	71.39%
CYP2C19 inhibition	-	0.7306	73.06%
CYP2D6 inhibition	-	0.9173	91.73%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.8613	86.13%
CYP inhibitory promiscuity	-	0.9337	93.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6129	61.29%
Eye corrosion	-	0.8058	80.58%
Eye irritation	+	0.8973	89.73%
Skin irritation	-	0.5578	55.78%
Skin corrosion	-	0.9721	97.21%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6659	66.59%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.6836	68.36%
Respiratory toxicity	-	0.7667	76.67%
Reproductive toxicity	-	0.6402	64.02%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6374	63.74%
Acute Oral Toxicity (c)	III	0.7814	78.14%
Estrogen receptor binding	-	0.5561	55.61%
Androgen receptor binding	-	0.6691	66.91%
Thyroid receptor binding	-	0.5661	56.61%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5398	53.98%
PPAR gamma	+	0.6091	60.91%
Honey bee toxicity	-	0.9453	94.53%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9967	99.67%

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	91.86%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.29%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.90%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.21%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.28%	91.19%
CHEMBL217	P14416	Dopamine D2 receptor	81.65%	95.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.37%	92.94%

Plants that contains it

• Lindera glauca

Cross-Links

• PubChem: 101667071
• LOTUS: LTS0100377
• wikiData: Q104402880