(2R,3S,4S)-3-(hydroxymethyl)-4-[(E)-5-hydroxy-5-methyl-1-methylene-hex-3-enyl]-2-methyl-cyclopentanone

Details

• Internal ID: 097ff6d7-0124-4e30-b22c-641f601f7d2d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R,3S,4S)-3-(hydroxymethyl)-4-[(4E)-6-hydroxy-6-methylhepta-1,4-dien-2-yl]-2-methylcyclopentan-1-one
• SMILES (Canonical): CC1C(C(CC1=O)C(=C)CC=CC(C)(C)O)CO
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](CC1=O)C(=C)C/C=C/C(C)(C)O)CO
• InChI: InChI=1S/C15H24O3/c1-10(6-5-7-15(3,4)18)12-8-14(17)11(2)13(12)9-16/h5,7,11-13,16,18H,1,6,8-9H2,2-4H3/b7-5+/t11-,12-,13-/m1/s1
• InChI Key: DEBVTYMFDLFRGC-AIIKUZRDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• (2R,3S,4S)-3-(hydroxymethyl)-4-[(E)-5-hydroxy-5-methyl-1-methylene-hex-3-enyl]-2-methyl-cyclopentanone
• Cyclopentanone, 3-(hydroxymethyl)-4-[(3E)-5-hydroxy-5-methyl-1-methylene-3-hexenyl]-2-methyl-, (2R,3S,4S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	+	0.5250	52.50%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7741	77.41%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8828	88.28%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7593	75.93%
BSEP inhibitior	-	0.7969	79.69%
P-glycoprotein inhibitior	-	0.9417	94.17%
P-glycoprotein substrate	-	0.8788	87.88%
CYP3A4 substrate	-	0.5097	50.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8443	84.43%
CYP3A4 inhibition	-	0.7401	74.01%
CYP2C9 inhibition	-	0.8233	82.33%
CYP2C19 inhibition	-	0.7831	78.31%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.8190	81.90%
CYP2C8 inhibition	-	0.9106	91.06%
CYP inhibitory promiscuity	-	0.8045	80.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8067	80.67%
Carcinogenicity (trinary)	Non-required	0.6577	65.77%
Eye corrosion	-	0.9665	96.65%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.6333	63.33%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6040	60.40%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	+	0.4767	47.67%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5312	53.12%
Acute Oral Toxicity (c)	III	0.6603	66.03%
Estrogen receptor binding	-	0.7087	70.87%
Androgen receptor binding	-	0.5131	51.31%
Thyroid receptor binding	-	0.5823	58.23%
Glucocorticoid receptor binding	+	0.5954	59.54%
Aromatase binding	-	0.8153	81.53%
PPAR gamma	-	0.6716	67.16%
Honey bee toxicity	-	0.8887	88.87%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9669	96.69%

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	93.91%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.87%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.06%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.98%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.35%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.60%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	84.97%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.52%	97.09%

Plants that contains it

• Glycosmis macrophylla
• Litsea verticillata

Cross-Links

• PubChem: 5279293
• LOTUS: LTS0041041
• wikiData: Q105027765