Huperzine R

Details

• Internal ID: ce389478-f169-4a8b-8e8a-eb4415338bc1
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: (1S,6R)-6-methyl-2-oxa-9-azatricyclo[7.4.3.04,13]hexadec-4(13)-ene-3,8-dione
• SMILES (Canonical): CC1CC2=C3CCCN(CCCC3OC2=O)C(=O)C1
• SMILES (Isomeric): C[C@@H]1CC2=C3CCCN(CCC[C@@H]3OC2=O)C(=O)C1
• InChI: InChI=1S/C15H21NO3/c1-10-8-12-11-4-2-6-16(14(17)9-10)7-3-5-13(11)19-15(12)18/h10,13H,2-9H2,1H3/t10-,13+/m1/s1
• InChI Key: JNUJNSFROLCMND-MFKMUULPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.33 g/mol
• Exact Mass: 263.15214353 g/mol
• Topological Polar Surface Area (TPSA): 46.60 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.04
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• CHEMBL510841
• (1S,6R)-6-methyl-2-oxa-9-azatricyclo[7.4.3.04,13]hexadec-4(13)-ene-3,8-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.8620	86.20%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6049	60.49%
OATP2B1 inhibitior	-	0.8499	84.99%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.7020	70.20%
P-glycoprotein inhibitior	-	0.8606	86.06%
P-glycoprotein substrate	-	0.7138	71.38%
CYP3A4 substrate	+	0.5272	52.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8926	89.26%
CYP3A4 inhibition	-	0.9227	92.27%
CYP2C9 inhibition	-	0.8514	85.14%
CYP2C19 inhibition	-	0.5774	57.74%
CYP2D6 inhibition	-	0.9202	92.02%
CYP1A2 inhibition	-	0.6890	68.90%
CYP2C8 inhibition	-	0.9478	94.78%
CYP inhibitory promiscuity	-	0.9510	95.10%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4411	44.11%
Eye corrosion	-	0.9591	95.91%
Eye irritation	-	0.6933	69.33%
Skin irritation	-	0.7600	76.00%
Skin corrosion	-	0.8638	86.38%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6460	64.60%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.8481	84.81%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6398	63.98%
Acute Oral Toxicity (c)	III	0.6048	60.48%
Estrogen receptor binding	-	0.8770	87.70%
Androgen receptor binding	-	0.5304	53.04%
Thyroid receptor binding	-	0.5636	56.36%
Glucocorticoid receptor binding	-	0.7288	72.88%
Aromatase binding	-	0.6663	66.63%
PPAR gamma	-	0.8508	85.08%
Honey bee toxicity	-	0.9372	93.72%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.3751	37.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.24%	95.56%
CHEMBL217	P14416	Dopamine D2 receptor	92.02%	95.62%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.31%	93.40%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.13%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.06%	99.23%
CHEMBL5203	P33316	dUTP pyrophosphatase	87.86%	99.18%
CHEMBL1902	P62942	FK506-binding protein 1A	85.04%	97.05%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.20%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.00%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.73%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.98%	86.33%
CHEMBL234	P35462	Dopamine D3 receptor	80.80%	90.48%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.40%	85.14%

Plants that contains it

• Huperzia serrata

Cross-Links

• PubChem: 636646
• LOTUS: LTS0185631
• wikiData: Q105132133