(4S,4aR,7S,7aR)-7-hydroxy-4-(hydroxymethyl)-7-methyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one

Details

• Internal ID: b501a495-f251-47d2-92f9-5e589890ace6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aR,7S,7aR)-7-hydroxy-4-(hydroxymethyl)-7-methyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1(CCC2C1COC(=O)C2CO)O
• SMILES (Isomeric): C[C@@]1(CC[C@@H]2[C@@H]1COC(=O)[C@@H]2CO)O
• InChI: InChI=1S/C10H16O4/c1-10(13)3-2-6-7(4-11)9(12)14-5-8(6)10/h6-8,11,13H,2-5H2,1H3/t6-,7+,8-,10-/m0/s1
• InChI Key: ZYYAVDNIJGWUML-ODHVRURNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23 g/mol
• Exact Mass: 200.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.07
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9146	91.46%
Caco-2	-	0.7029	70.29%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6820	68.20%
OATP2B1 inhibitior	-	0.8429	84.29%
OATP1B1 inhibitior	+	0.9242	92.42%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7169	71.69%
BSEP inhibitior	-	0.9585	95.85%
P-glycoprotein inhibitior	-	0.9738	97.38%
P-glycoprotein substrate	-	0.8428	84.28%
CYP3A4 substrate	+	0.5436	54.36%
CYP2C9 substrate	-	0.7953	79.53%
CYP2D6 substrate	-	0.8523	85.23%
CYP3A4 inhibition	-	0.8856	88.56%
CYP2C9 inhibition	-	0.9353	93.53%
CYP2C19 inhibition	-	0.8993	89.93%
CYP2D6 inhibition	-	0.9629	96.29%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	-	0.9382	93.82%
CYP inhibitory promiscuity	-	0.9821	98.21%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6426	64.26%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.6242	62.42%
Skin irritation	-	0.6624	66.24%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.6678	66.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6902	69.02%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5141	51.41%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7009	70.09%
Acute Oral Toxicity (c)	III	0.4829	48.29%
Estrogen receptor binding	-	0.5645	56.45%
Androgen receptor binding	+	0.6511	65.11%
Thyroid receptor binding	-	0.7547	75.47%
Glucocorticoid receptor binding	-	0.7008	70.08%
Aromatase binding	-	0.8802	88.02%
PPAR gamma	-	0.8848	88.48%
Honey bee toxicity	-	0.8998	89.98%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.6991	69.91%

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	96.87%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.37%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.31%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.59%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.71%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.10%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.01%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	81.99%	95.93%

Plants that contains it

• Cymbaria mongolica

Cross-Links

• PubChem: 162869025
• LOTUS: LTS0229132
• wikiData: Q105386538