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

Details

• Internal ID: 10ae805a-c42c-4147-a0ba-870bac0031fc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Pseudoguaianes
• IUPAC Name: 2-[(3S,3aS,8S,8aS)-3-hydroxy-3a,8-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-azulen-5-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(CC2(C1CCC2O)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H]1CCC(C[C@]2([C@H]1CC[C@@H]2O)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H24O3/c1-9-4-5-11(10(2)14(17)18)8-15(3)12(9)6-7-13(15)16/h9,11-13,16H,2,4-8H2,1,3H3,(H,17,18)/t9-,11?,12-,13-,15-/m0/s1
• InChI Key: VTJQRZKWDGRSMU-ANQIZZJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9926	99.26%
Caco-2	+	0.8423	84.23%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6808	68.08%
OATP2B1 inhibitior	-	0.8505	85.05%
OATP1B1 inhibitior	+	0.9335	93.35%
OATP1B3 inhibitior	+	0.8877	88.77%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5319	53.19%
BSEP inhibitior	-	0.8967	89.67%
P-glycoprotein inhibitior	-	0.9213	92.13%
P-glycoprotein substrate	-	0.8322	83.22%
CYP3A4 substrate	+	0.6329	63.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.8869	88.69%
CYP2C9 inhibition	-	0.8668	86.68%
CYP2C19 inhibition	-	0.8686	86.86%
CYP2D6 inhibition	-	0.9394	93.94%
CYP1A2 inhibition	-	0.6705	67.05%
CYP2C8 inhibition	-	0.7913	79.13%
CYP inhibitory promiscuity	-	0.9561	95.61%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5544	55.44%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.7379	73.79%
Skin irritation	+	0.5872	58.72%
Skin corrosion	-	0.9375	93.75%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7199	71.99%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.5742	57.42%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8456	84.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6975	69.75%
Acute Oral Toxicity (c)	III	0.4829	48.29%
Estrogen receptor binding	+	0.7557	75.57%
Androgen receptor binding	-	0.5154	51.54%
Thyroid receptor binding	-	0.5568	55.68%
Glucocorticoid receptor binding	+	0.6681	66.81%
Aromatase binding	-	0.5313	53.13%
PPAR gamma	-	0.5275	52.75%
Honey bee toxicity	-	0.9092	90.92%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9912	99.12%

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	95.21%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	95.13%	96.38%
CHEMBL4040	P28482	MAP kinase ERK2	94.18%	83.82%
CHEMBL1951	P21397	Monoamine oxidase A	90.48%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.44%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	84.33%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.55%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.53%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.43%	96.47%
CHEMBL221	P23219	Cyclooxygenase-1	81.03%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.36%	97.25%

Plants that contains it

• Xanthium strumarium

Cross-Links

• PubChem: 102056126
• LOTUS: LTS0258155
• wikiData: Q105292776