Prelaureatin

Details

• Internal ID: 729575a8-d9e2-40b0-aae4-6301bea00d62
• Taxonomy: Organoheterocyclic compounds > Oxocins
• IUPAC Name: (2S,3S,5Z,8R)-8-[(1S)-1-bromopropyl]-2-[(Z)-pent-2-en-4-ynyl]-3,4,7,8-tetrahydro-2H-oxocin-3-ol
• SMILES (Canonical): CCC(C1CC=CCC(C(O1)CC=CC#C)O)Br
• SMILES (Isomeric): CC[C@@H]([C@H]1C/C=C\C[C@@H]([C@@H](O1)C/C=C\C#C)O)Br
• InChI: InChI=1S/C15H21BrO2/c1-3-5-6-11-15-13(17)9-7-8-10-14(18-15)12(16)4-2/h1,5-8,12-15,17H,4,9-11H2,2H3/b6-5-,8-7-/t12-,13-,14+,15-/m0/s1
• InChI Key: OHHPIXHKUDAQAW-WVZXMNBZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁BrO₂
• Molecular Weight: 313.23 g/mol
• Exact Mass: 312.07249 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (2S,3S,5Z,8R)-8-[(1S)-1-bromopropyl]-2-[(Z)-pent-2-en-4-ynyl]-3,4,7,8-tetrahydro-2H-oxocin-3-ol
• 139610-22-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.5300	53.00%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4701	47.01%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8147	81.47%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8435	84.35%
P-glycoprotein inhibitior	-	0.8921	89.21%
P-glycoprotein substrate	-	0.8565	85.65%
CYP3A4 substrate	+	0.5076	50.76%
CYP2C9 substrate	-	0.6077	60.77%
CYP2D6 substrate	-	0.7797	77.97%
CYP3A4 inhibition	-	0.7341	73.41%
CYP2C9 inhibition	-	0.7738	77.38%
CYP2C19 inhibition	-	0.6106	61.06%
CYP2D6 inhibition	-	0.9214	92.14%
CYP1A2 inhibition	-	0.6916	69.16%
CYP2C8 inhibition	-	0.8614	86.14%
CYP inhibitory promiscuity	-	0.6932	69.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7054	70.54%
Carcinogenicity (trinary)	Danger	0.4099	40.99%
Eye corrosion	-	0.8946	89.46%
Eye irritation	-	0.9940	99.40%
Skin irritation	-	0.5811	58.11%
Skin corrosion	-	0.7981	79.81%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4517	45.17%
Micronuclear	-	0.6826	68.26%
Hepatotoxicity	-	0.5571	55.71%
skin sensitisation	+	0.5743	57.43%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5825	58.25%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6226	62.26%
Acute Oral Toxicity (c)	III	0.6516	65.16%
Estrogen receptor binding	-	0.5712	57.12%
Androgen receptor binding	-	0.6725	67.25%
Thyroid receptor binding	-	0.5390	53.90%
Glucocorticoid receptor binding	+	0.6097	60.97%
Aromatase binding	-	0.7351	73.51%
PPAR gamma	+	0.5324	53.24%
Honey bee toxicity	-	0.8957	89.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7716	77.16%

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	96.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	93.14%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.06%	96.61%
CHEMBL2581	P07339	Cathepsin D	88.89%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.39%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	87.12%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.64%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.62%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.14%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.24%	94.45%

Plants that contains it

• Eleutherococcus giraldii
• Lespedeza davidii
• Solanum aethiopicum
• Tectona grandis

Cross-Links

• PubChem: 10870702
• NPASS: NPC97632
• LOTUS: LTS0270516
• wikiData: Q105192083