(3S,4R,4aR,7S,7aR)-3-hydroxy-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one

Details

• Internal ID: 712e681a-6cc4-41d6-84e4-b09e233df23f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3S,4R,4aR,7S,7aR)-3-hydroxy-4,7-dimethyl-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one
• SMILES (Canonical): CC1CCC2C1C(=O)OC(C2C)O
• SMILES (Isomeric): C[C@H]1CC[C@H]2[C@@H]1C(=O)O[C@@H]([C@@H]2C)O
• InChI: InChI=1S/C10H16O3/c1-5-3-4-7-6(2)9(11)13-10(12)8(5)7/h5-9,11H,3-4H2,1-2H3/t5-,6+,7+,8+,9-/m0/s1
• InChI Key: PLWVFYKDQKCFIY-CBHQDSPSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.23 g/mol
• Exact Mass: 184.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.16
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• PLWVFYKDQKCFIY-CBHQDSPSSA-N
• (3S,4R,4aR,7S,7aR)-3-hydroxy-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9713	97.13%
Caco-2	+	0.6175	61.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4253	42.53%
OATP2B1 inhibitior	-	0.8441	84.41%
OATP1B1 inhibitior	+	0.9451	94.51%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9796	97.96%
P-glycoprotein inhibitior	-	0.9617	96.17%
P-glycoprotein substrate	-	0.8626	86.26%
CYP3A4 substrate	-	0.5490	54.90%
CYP2C9 substrate	-	0.6157	61.57%
CYP2D6 substrate	-	0.8452	84.52%
CYP3A4 inhibition	-	0.9189	91.89%
CYP2C9 inhibition	-	0.9038	90.38%
CYP2C19 inhibition	-	0.9192	91.92%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.5273	52.73%
CYP2C8 inhibition	-	0.9771	97.71%
CYP inhibitory promiscuity	-	0.9838	98.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6617	66.17%
Eye corrosion	-	0.8637	86.37%
Eye irritation	-	0.5851	58.51%
Skin irritation	+	0.6271	62.71%
Skin corrosion	-	0.6398	63.98%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7854	78.54%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6076	60.76%
skin sensitisation	-	0.7312	73.12%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6330	63.30%
Acute Oral Toxicity (c)	III	0.4893	48.93%
Estrogen receptor binding	-	0.8377	83.77%
Androgen receptor binding	-	0.5624	56.24%
Thyroid receptor binding	-	0.7433	74.33%
Glucocorticoid receptor binding	-	0.8751	87.51%
Aromatase binding	-	0.9027	90.27%
PPAR gamma	-	0.8044	80.44%
Honey bee toxicity	-	0.9281	92.81%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.8260	82.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.49%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.29%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.24%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.49%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.52%	98.46%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.44%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.28%	89.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.82%	86.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.47%	97.09%

Plants that contains it

• Nepeta tuberosa

Cross-Links

• PubChem: 12313275
• LOTUS: LTS0058406
• wikiData: Q105211291