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

Details

• Internal ID: e56068d8-d8b1-45e7-8bc6-e5b685a2c76a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4R,4aS,7R,7aR)-4-(hydroxymethyl)-7-methyl-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1CCC2C1COC(=O)C2CO
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@@H]1COC(=O)[C@H]2CO
• InChI: InChI=1S/C10H16O3/c1-6-2-3-7-8(4-11)10(12)13-5-9(6)7/h6-9,11H,2-5H2,1H3/t6-,7-,8+,9-/m1/s1
• InChI Key: OWXGCULHKDQVDN-LURQLKTLSA-N
• Popularity: 1 reference 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: 1.90
• Atomic LogP (AlogP): 0.81
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9591	95.91%
Caco-2	-	0.5534	55.34%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.4436	44.36%
OATP2B1 inhibitior	-	0.8439	84.39%
OATP1B1 inhibitior	+	0.9391	93.91%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6317	63.17%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.9796	97.96%
P-glycoprotein substrate	-	0.8849	88.49%
CYP3A4 substrate	-	0.5683	56.83%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8369	83.69%
CYP3A4 inhibition	-	0.9232	92.32%
CYP2C9 inhibition	-	0.8524	85.24%
CYP2C19 inhibition	-	0.7702	77.02%
CYP2D6 inhibition	-	0.9318	93.18%
CYP1A2 inhibition	-	0.6651	66.51%
CYP2C8 inhibition	-	0.9589	95.89%
CYP inhibitory promiscuity	-	0.9671	96.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6705	67.05%
Eye corrosion	-	0.9291	92.91%
Eye irritation	+	0.7967	79.67%
Skin irritation	-	0.6585	65.85%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.5778	57.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7430	74.30%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.5835	58.35%
skin sensitisation	-	0.8587	85.87%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5439	54.39%
Acute Oral Toxicity (c)	III	0.5982	59.82%
Estrogen receptor binding	-	0.7759	77.59%
Androgen receptor binding	+	0.5784	57.84%
Thyroid receptor binding	-	0.8228	82.28%
Glucocorticoid receptor binding	-	0.7748	77.48%
Aromatase binding	-	0.9219	92.19%
PPAR gamma	-	0.9246	92.46%
Honey bee toxicity	-	0.9159	91.59%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.8985	89.85%

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	95.37%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.89%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.30%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.53%	91.11%
CHEMBL2581	P07339	Cathepsin D	87.44%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.29%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.84%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.70%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.93%	85.14%

Plants that contains it

• Boschniakia rossica

Cross-Links

• PubChem: 12109335
• NPASS: NPC312945
• LOTUS: LTS0100137
• wikiData: Q105202371