(4R,4aR,6S,7S,7aS)-6-hydroxy-7-(hydroxymethyl)-4-methyl-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one

Details

• Internal ID: c72a82e7-5eda-4f69-9cbb-6553fde62eb1
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aR,6S,7S,7aS)-6-hydroxy-7-(hydroxymethyl)-4-methyl-4,4a,5,6,7,7a-hexahydro-3H-cyclopenta[c]pyran-1-one
• SMILES (Canonical): CC1COC(=O)C2C1CC(C2CO)O
• SMILES (Isomeric): C[C@H]1COC(=O)[C@H]2[C@@H]1C[C@@H]([C@@H]2CO)O
• InChI: InChI=1S/C10H16O4/c1-5-4-14-10(13)9-6(5)2-8(12)7(9)3-11/h5-9,11-12H,2-4H2,1H3/t5-,6+,7-,8-,9-/m0/s1
• InChI Key: STSJHYHSVQPPEC-BGKGJTHRSA-N
• Popularity: 2 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: 0.50
• Atomic LogP (AlogP): -0.22
• 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	+	0.8302	83.02%
Caco-2	-	0.6078	60.78%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5405	54.05%
OATP2B1 inhibitior	-	0.8427	84.27%
OATP1B1 inhibitior	+	0.9313	93.13%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9567	95.67%
BSEP inhibitior	-	0.9737	97.37%
P-glycoprotein inhibitior	-	0.9667	96.67%
P-glycoprotein substrate	-	0.8202	82.02%
CYP3A4 substrate	-	0.5567	55.67%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8260	82.60%
CYP3A4 inhibition	-	0.9142	91.42%
CYP2C9 inhibition	-	0.9581	95.81%
CYP2C19 inhibition	-	0.8981	89.81%
CYP2D6 inhibition	-	0.9432	94.32%
CYP1A2 inhibition	-	0.8719	87.19%
CYP2C8 inhibition	-	0.9842	98.42%
CYP inhibitory promiscuity	-	0.9695	96.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7248	72.48%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.8251	82.51%
Skin irritation	-	0.7711	77.11%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.6415	64.15%
Human Ether-a-go-go-Related Gene inhibition	-	0.7470	74.70%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6126	61.26%
skin sensitisation	-	0.9249	92.49%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5464	54.64%
Acute Oral Toxicity (c)	III	0.5003	50.03%
Estrogen receptor binding	-	0.6418	64.18%
Androgen receptor binding	+	0.6329	63.29%
Thyroid receptor binding	-	0.7567	75.67%
Glucocorticoid receptor binding	-	0.7799	77.99%
Aromatase binding	-	0.8841	88.41%
PPAR gamma	-	0.8383	83.83%
Honey bee toxicity	-	0.8897	88.97%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7133	71.33%

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	93.48%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.79%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.89%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.26%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.23%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.29%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.94%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.25%	89.34%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.91%	86.92%

Plants that contains it

• Asparagus africanus
• Camellia sinensis
• Kadsura heteroclita
• Orobanche variegata
• Penstemon newberryi
• Solanum chilense
• Valeriana laxiflora

Cross-Links

• PubChem: 45096715
• NPASS: NPC129796
• LOTUS: LTS0248499
• wikiData: Q105260596