(3aS,5S,6R,8aS)-5-hydroxy-7-[(3R)-3-hydroxybutyl]-6-methyl-3-methylidene-4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: 5104309b-a0fc-4fb2-8cf3-a3fd0cbc57c0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aS,5S,6R,8aS)-5-hydroxy-7-[(3R)-3-hydroxybutyl]-6-methyl-3-methylidene-4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• InChI: InChI=1S/C15H22O4/c1-8(16)4-5-11-6-14-12(7-13(17)9(11)2)10(3)15(18)19-14/h6,8-9,12-14,16-17H,3-5,7H2,1-2H3/t8-,9-,12+,13+,14+/m1/s1
• InChI Key: CRJYIDXYIZSNHX-IZPVPAKOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.5808	58.08%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5787	57.87%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8580	85.80%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7820	78.20%
BSEP inhibitior	-	0.9645	96.45%
P-glycoprotein inhibitior	-	0.9034	90.34%
P-glycoprotein substrate	-	0.6714	67.14%
CYP3A4 substrate	+	0.5536	55.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8270	82.70%
CYP3A4 inhibition	-	0.6017	60.17%
CYP2C9 inhibition	-	0.8794	87.94%
CYP2C19 inhibition	-	0.8093	80.93%
CYP2D6 inhibition	-	0.9083	90.83%
CYP1A2 inhibition	-	0.5451	54.51%
CYP2C8 inhibition	-	0.9321	93.21%
CYP inhibitory promiscuity	-	0.8804	88.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6500	65.00%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9070	90.70%
Skin irritation	-	0.5782	57.82%
Skin corrosion	-	0.8951	89.51%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7415	74.15%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.7143	71.43%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.7199	71.99%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8781	87.81%
Acute Oral Toxicity (c)	III	0.3741	37.41%
Estrogen receptor binding	-	0.6608	66.08%
Androgen receptor binding	-	0.6158	61.58%
Thyroid receptor binding	+	0.5466	54.66%
Glucocorticoid receptor binding	+	0.7255	72.55%
Aromatase binding	-	0.7441	74.41%
PPAR gamma	-	0.6889	68.89%
Honey bee toxicity	-	0.8092	80.92%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9746	97.46%

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	98.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	96.20%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.05%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	95.34%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.32%	91.11%
CHEMBL2996	Q05655	Protein kinase C delta	92.30%	97.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.35%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.73%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.41%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.20%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	83.19%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.16%	96.61%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.48%	96.37%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.11%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.03%	86.33%

Plants that contains it

• Dicoria canescens

Cross-Links

• PubChem: 163026047
• LOTUS: LTS0090963
• wikiData: Q104968569