2-[(3aS,5R,7aS)-3-acetyl-3a-hydroxy-7a-methyl-2,3,4,5,6,7-hexahydro-1H-inden-5-yl]prop-2-enoic acid

Details

• Internal ID: 55a8df72-e04e-4375-b74c-30588440040a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(3aS,5R,7aS)-3-acetyl-3a-hydroxy-7a-methyl-2,3,4,5,6,7-hexahydro-1H-inden-5-yl]prop-2-enoic acid
• SMILES (Canonical): CC(=O)C1CCC2(C1(CC(CC2)C(=C)C(=O)O)O)C
• SMILES (Isomeric): CC(=O)C1CC[C@]2([C@@]1(C[C@@H](CC2)C(=C)C(=O)O)O)C
• InChI: InChI=1S/C15H22O4/c1-9(13(17)18)11-4-6-14(3)7-5-12(10(2)16)15(14,19)8-11/h11-12,19H,1,4-8H2,2-3H3,(H,17,18)/t11-,12?,14+,15+/m1/s1
• InChI Key: YLMSJTAFOFIDRW-PYZCBOGGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.6720	67.20%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7920	79.20%
OATP2B1 inhibitior	-	0.8501	85.01%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	-	0.2343	23.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6287	62.87%
BSEP inhibitior	-	0.8804	88.04%
P-glycoprotein inhibitior	-	0.9247	92.47%
P-glycoprotein substrate	-	0.8171	81.71%
CYP3A4 substrate	+	0.5537	55.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9027	90.27%
CYP3A4 inhibition	-	0.8755	87.55%
CYP2C9 inhibition	-	0.9268	92.68%
CYP2C19 inhibition	-	0.9500	95.00%
CYP2D6 inhibition	-	0.9554	95.54%
CYP1A2 inhibition	-	0.8297	82.97%
CYP2C8 inhibition	-	0.8843	88.43%
CYP inhibitory promiscuity	-	0.9787	97.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5764	57.64%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.4806	48.06%
Skin irritation	+	0.6730	67.30%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.6960	69.60%
Human Ether-a-go-go-Related Gene inhibition	-	0.6614	66.14%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.7041	70.41%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.6754	67.54%
Acute Oral Toxicity (c)	I	0.4422	44.22%
Estrogen receptor binding	+	0.8697	86.97%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5578	55.78%
Glucocorticoid receptor binding	+	0.6727	67.27%
Aromatase binding	+	0.5461	54.61%
PPAR gamma	+	0.5601	56.01%
Honey bee toxicity	-	0.9019	90.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	96.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.88%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	88.71%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	84.32%	90.17%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.66%	96.38%

Plants that contains it

• Chiliadenus candicans

Cross-Links

• PubChem: 15161369
• LOTUS: LTS0137894
• wikiData: Q105350196