(+/-)-Huperzine A

Details

• Internal ID: 4f8af520-0084-4f8b-9933-8c5ece7ef691
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives
• IUPAC Name: (13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
• SMILES (Canonical): CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
• SMILES (Isomeric): C/C=C/1\C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
• InChI: InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+
• InChI Key: ZRJBHWIHUMBLCN-QDEBKDIKSA-N
• Popularity: 1,012 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈N₂O
• Molecular Weight: 242.32 g/mol
• Exact Mass: 242.141913202 g/mol
• Topological Polar Surface Area (TPSA): 55.10 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 2.00
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 120786-18-7
• (+/-)-Huperzine A
• ( inverted exclamation markA)-Huperzine A
• Fordine
• HuperzineA
• Huperizine A
• Huperzine-A
• (-)-huperzine A
• (+)-Huperzine A
• (-)-Huperzine A (HupA)
• 102518-79-6
• NCGC00159362-02
• (?)-Huperazine A
• (??)-Huperzine A
• SCHEMBL679315
• CHEMBL394259
• SCHEMBL1047469
• CHEBI:91724
• Huperzine A [(-)-Huperzine A]
• DTXSID801115670
• HMS1362I05
• HMS1792I05
• HMS3403I05
• 103735-86-0
• AKOS016004635
• AKOS022661860
• AKOS026750633
• CS-1089
• NCGC00163246-02
• NCGC00163246-03
• 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-
• AS-75811
• HY-17388
• (+/-)-Huperzine A, synthetic, >=98% (TLC)
• BRD-A47065382-001-02-9
• (11E)-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one
• (13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5,10-tetraen-5-ol
• (AfAE'A centa' notA inverted exclamation markAfasA'A inverted exclamation markAfAE'Adaggeratrade markAfA centA centa' notA inverted exclamation markA'A not)-Huperzine A

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	-	0.7043	70.43%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Lysosomes	0.3963	39.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7619	76.19%
P-glycoprotein inhibitior	-	0.9420	94.20%
P-glycoprotein substrate	-	0.6904	69.04%
CYP3A4 substrate	+	0.5429	54.29%
CYP2C9 substrate	-	0.7905	79.05%
CYP2D6 substrate	-	0.8194	81.94%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	+	0.6166	61.66%
CYP2C19 inhibition	+	0.5397	53.97%
CYP2D6 inhibition	-	0.7873	78.73%
CYP1A2 inhibition	+	0.5759	57.59%
CYP2C8 inhibition	-	0.7910	79.10%
CYP inhibitory promiscuity	+	0.8312	83.12%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5235	52.35%
Eye corrosion	-	0.9827	98.27%
Eye irritation	-	0.9884	98.84%
Skin irritation	-	0.7883	78.83%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7283	72.83%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5356	53.56%
skin sensitisation	-	0.8199	81.99%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4770	47.70%
Acute Oral Toxicity (c)	I	0.4404	44.04%
Estrogen receptor binding	-	0.5640	56.40%
Androgen receptor binding	-	0.5245	52.45%
Thyroid receptor binding	+	0.6139	61.39%
Glucocorticoid receptor binding	+	0.7171	71.71%
Aromatase binding	-	0.6647	66.47%
PPAR gamma	+	0.7395	73.95%
Honey bee toxicity	-	0.8758	87.58%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8543	85.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	33 nM; 0.54 nM	IC50; IC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.66%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.78%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.46%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.68%	94.45%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.50%	85.30%
CHEMBL2581	P07339	Cathepsin D	86.91%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.16%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.64%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.00%	94.75%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.19%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.81%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.15%	93.00%

Plants that contains it

• Huperzia selago
• Huperzia serrata

Cross-Links

• PubChem: 5912039
• LOTUS: LTS0248646
• wikiData: Q105382024