methyl (3aR,3bR,5S,6aR,7aS)-2,7a-dihydroxy-3,3a,5-trimethyl-1-oxo-4,6,6a,7-tetrahydro-3bH-cyclopenta[a]pentalene-5-carboxylate

Details

• Internal ID: b1f4dfc1-bcb7-4a56-8242-3baa9bafc27e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Triquinane sesquiterpenoids > Linear triquinanes
• IUPAC Name: methyl (3aR,3bR,5S,6aR,7aS)-2,7a-dihydroxy-3,3a,5-trimethyl-1-oxo-4,6,6a,7-tetrahydro-3bH-cyclopenta[a]pentalene-5-carboxylate
• SMILES (Canonical): CC1=C(C(=O)C2(C1(C3CC(CC3C2)(C)C(=O)OC)C)O)O
• SMILES (Isomeric): CC1=C(C(=O)[C@]2([C@@]1([C@@H]3C[C@@](C[C@@H]3C2)(C)C(=O)OC)C)O)O
• InChI: InChI=1S/C16H22O5/c1-8-11(17)12(18)16(20)6-9-5-14(2,13(19)21-4)7-10(9)15(8,16)3/h9-10,17,20H,5-7H2,1-4H3/t9-,10-,14+,15+,16-/m1/s1
• InChI Key: BZEAXBLCXACAHJ-OLGBICLBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.34 g/mol
• Exact Mass: 294.14672380 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• methyl (3aR,3bR,5S,6aR,7aS)-2,7a-dihydroxy-3,3a,5-trimethyl-1-oxo-4,6,6a,7-tetrahydro-3bH-cyclopenta[a]pentalene-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9620	96.20%
Caco-2	+	0.8460	84.60%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5964	59.64%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9231	92.31%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7245	72.45%
P-glycoprotein inhibitior	-	0.9322	93.22%
P-glycoprotein substrate	-	0.7626	76.26%
CYP3A4 substrate	+	0.6163	61.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9078	90.78%
CYP3A4 inhibition	-	0.7475	74.75%
CYP2C9 inhibition	-	0.8526	85.26%
CYP2C19 inhibition	-	0.8587	85.87%
CYP2D6 inhibition	-	0.9462	94.62%
CYP1A2 inhibition	-	0.7313	73.13%
CYP2C8 inhibition	-	0.8082	80.82%
CYP inhibitory promiscuity	-	0.9669	96.69%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8905	89.05%
Skin irritation	+	0.5141	51.41%
Skin corrosion	-	0.9493	94.93%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3682	36.82%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.5828	58.28%
skin sensitisation	-	0.7948	79.48%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6348	63.48%
Acute Oral Toxicity (c)	I	0.3482	34.82%
Estrogen receptor binding	+	0.7068	70.68%
Androgen receptor binding	+	0.5985	59.85%
Thyroid receptor binding	+	0.6672	66.72%
Glucocorticoid receptor binding	-	0.6688	66.88%
Aromatase binding	-	0.5706	57.06%
PPAR gamma	-	0.5981	59.81%
Honey bee toxicity	-	0.8609	86.09%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9693	96.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.19%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.55%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.02%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.28%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.17%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	83.69%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.86%	94.33%

Plants that contains it

• Pachysandra procumbens

Cross-Links

• PubChem: 102227585
• NPASS: NPC281758
• LOTUS: LTS0259342
• wikiData: Q105155819