(3aS,3bR,5S,6aS,7aR)-2-hydroxy-3,3a,5-trimethyl-1-oxo-3b,4,6,6a,7,7a-hexahydrocyclopenta[a]pentalene-5-carboxylic acid

Details

• Internal ID: 8feb9637-6b05-40ad-8a68-12410cd5f8db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Triquinane sesquiterpenoids > Linear triquinanes
• IUPAC Name: (3aS,3bR,5S,6aS,7aR)-2-hydroxy-3,3a,5-trimethyl-1-oxo-3b,4,6,6a,7,7a-hexahydrocyclopenta[a]pentalene-5-carboxylic acid
• SMILES (Canonical): CC1=C(C(=O)C2C1(C3CC(CC3C2)(C)C(=O)O)C)O
• SMILES (Isomeric): CC1=C(C(=O)[C@H]2[C@@]1([C@@H]3C[C@@](C[C@@H]3C2)(C)C(=O)O)C)O
• InChI: InChI=1S/C15H20O4/c1-7-11(16)12(17)9-4-8-5-14(2,13(18)19)6-10(8)15(7,9)3/h8-10,16H,4-6H2,1-3H3,(H,18,19)/t8-,9-,10+,14-,15+/m0/s1
• InChI Key: BXFARSQJYWGLAG-UZGCMYEVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• (3aS,3bR,5S,6aS,7aR)-2-hydroxy-3,3a,5-trimethyl-1-oxo-3b,4,6,6a,7,7a-hexahydrocyclopenta[a]pentalene-5-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.5708	57.08%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7300	73.00%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.8945	89.45%
OATP1B3 inhibitior	+	0.8891	88.91%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8433	84.33%
P-glycoprotein inhibitior	-	0.9670	96.70%
P-glycoprotein substrate	-	0.7810	78.10%
CYP3A4 substrate	+	0.5599	55.99%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.9027	90.27%
CYP3A4 inhibition	-	0.7775	77.75%
CYP2C9 inhibition	-	0.8793	87.93%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.7752	77.52%
CYP2C8 inhibition	-	0.9260	92.60%
CYP inhibitory promiscuity	-	0.9502	95.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5794	57.94%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.6581	65.81%
Skin irritation	+	0.5806	58.06%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6839	68.39%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6078	60.78%
skin sensitisation	-	0.5823	58.23%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4934	49.34%
Acute Oral Toxicity (c)	III	0.4450	44.50%
Estrogen receptor binding	+	0.6725	67.25%
Androgen receptor binding	-	0.4884	48.84%
Thyroid receptor binding	+	0.6406	64.06%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5898	58.98%
PPAR gamma	-	0.6439	64.39%
Honey bee toxicity	-	0.9171	91.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9969	99.69%

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	90.99%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.65%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.64%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.71%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.95%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.51%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	83.98%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.98%	97.09%

Plants that contains it

• Pachysandra procumbens

Cross-Links

• PubChem: 102227584
• NPASS: NPC222749
• LOTUS: LTS0061258
• wikiData: Q104947901