(4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)-2-(2-methylpropanoyl)cyclopent-2-en-1-one

Details

• Internal ID: 23db3a42-e1a9-4b89-9bf0-99d6091c1c34
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Monocyclic monoterpenoids
• IUPAC Name: (4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)-2-(2-methylpropanoyl)cyclopent-2-en-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(C(C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• SMILES (Isomeric): CC(C)C(=O)C1=C([C@@]([C@@H](C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• InChI: InChI=1S/C20H28O5/c1-11(2)7-9-14-18(23)16(17(22)13(5)6)19(24)20(14,25)15(21)10-8-12(3)4/h7-8,13-14,24-25H,9-10H2,1-6H3/t14-,20-/m1/s1
• InChI Key: KKXFYHZSOIALRM-JLTOFOAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• (4S,5S)-2-(2-Methylpropanoyl)-3,4-dihydroxy-5-prenyl-4-(prenylcarbonyl)-2-cyclopentene-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9585	95.85%
Caco-2	-	0.5497	54.97%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8185	81.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9027	90.27%
OATP1B3 inhibitior	+	0.9364	93.64%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7642	76.42%
P-glycoprotein substrate	-	0.7281	72.81%
CYP3A4 substrate	+	0.5464	54.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.9537	95.37%
CYP2C9 inhibition	-	0.8191	81.91%
CYP2C19 inhibition	-	0.7580	75.80%
CYP2D6 inhibition	-	0.9051	90.51%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	-	0.9420	94.20%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9023	90.23%
Carcinogenicity (trinary)	Non-required	0.6369	63.69%
Eye corrosion	-	0.9735	97.35%
Eye irritation	-	0.7372	73.72%
Skin irritation	-	0.5894	58.94%
Skin corrosion	-	0.8828	88.28%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6457	64.57%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.5712	57.12%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6753	67.53%
Acute Oral Toxicity (c)	II	0.3597	35.97%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5281	52.81%
Thyroid receptor binding	+	0.5174	51.74%
Glucocorticoid receptor binding	+	0.6910	69.10%
Aromatase binding	+	0.5345	53.45%
PPAR gamma	+	0.8061	80.61%
Honey bee toxicity	-	0.8405	84.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9508	95.08%

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	96.75%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.27%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.39%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.07%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.21%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.79%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.67%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	83.29%	90.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.57%	96.47%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 44201359
• NPASS: NPC47047