NP-MRD: Showing NP-Card for (1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol (NP0246629)

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Record Information

Version

2.0

Created at

2022-09-07 08:10:04 UTC

Updated at

2022-09-07 08:10:05 UTC

NP-MRD ID

NP0246629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol

Description

Huperzine A, also known as selagine, belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group. (1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol is found in Phlegmariurus tetrastichus and Phlegmariurus varius. (1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol was first documented in 2003 (PMID: 12895686). Huperzine A is a very strong basic compound (based on its pKa) (PMID: 24299147) (PMID: 23306162) (PMID: 24129696) (PMID: 24190328).

Structure

MOL SDF PDB SMILES InChI

HUP
  Mrv0541 02231215502D          

 19 21  0  0  0  0            999 V2000
    1.0512   -2.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1679   -2.8281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2855   -1.7041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7001   -1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -0.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8177   -0.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1688   -0.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3040   -0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1541    0.6116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0390    0.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4945    2.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9017    1.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    1.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708    0.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7572    1.2022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916    0.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982   -0.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1044   -1.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218    1.1684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 19  1  1  0  0  0
 10 17  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC3=C(C=CC(=O)N3)[C@@](N)(CC(C)=C1)\C2=C\C

> <INCHI_IDENTIFIER>
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+/t10-,15+/m0/s1

> <INCHI_KEY>
ZRJBHWIHUMBLCN-YQEJDHNASA-N

> <FORMULA>
C15H18N2O

> <MOLECULAR_WEIGHT>
242.3162

> <EXACT_MASS>
242.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.874401840829073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
0.6177157886666669

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.107823071185413

> <JCHEM_PKA_STRONGEST_BASIC>
9.093326822285933

> <JCHEM_POLAR_SURFACE_AREA>
55.120000000000005

> <JCHEM_REFRACTIVITY>
75.79499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
huperaine A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HUP                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       1.962  -3.755   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.180  -5.279   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       0.533  -3.181   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.174  -2.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956  -1.279   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.526  -0.706   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.315  -1.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.567  -0.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.288   1.142   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.939   0.321   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.923   4.753   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.683   3.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.903   2.086   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.692   0.793   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.413   2.244   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.918   0.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.490  -1.173   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.062  -2.442   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       0.041   2.181   0.000  0.00  0.00           H+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1    7                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    3    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13   19                                             
CONECT   10    9   17                                                       
CONECT   11   12                                                            
CONECT   12   11   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14    6   13   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17                                                            
CONECT   19    9                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
(-)-Huperazine a	ChEBI
(-)-Selagine	ChEBI
Selagine	ChEBI
Huperzine a, (5alpha,9beta,11Z)-(-)-isomer	MeSH

Chemical Formula

C₁₅H₁₈N₂O

Average Mass

242.3162 Da

Monoisotopic Mass

242.14191 Da

IUPAC Name

(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one

Traditional Name

huperaine A

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C(C=CC(=O)N3)[C@@](N)(CC(C)=C1)\C2=C\C

InChI Identifier

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+/t10-,15+/m0/s1

InChI Key

ZRJBHWIHUMBLCN-YQEJDHNASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phlegmariurus tetrastichus	LOTUS Database	35616633
Phlegmariurus varius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolones and derivatives. Quinolones and derivatives are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Quinolones and derivatives

Alternative Parents

Substituents

Quinolone
Pyridinone
Aralkylamine
Pyridine
Heteroaromatic compound
Lactam
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:78330 )
primary amino compound (CHEBI:78330 )
pyridone (CHEBI:78330 )
sesquiterpene alkaloid (CHEBI:78330 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.78	ALOGPS
logP	0.62	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.8 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB04864

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Huperzine_A

METLIN ID

Not Available

PubChem Compound

854026

PDB ID

Not Available

ChEBI ID

78330

Good Scents ID

Not Available

References

General References

Ding R, Fu JG, Xu GQ, Sun BF, Lin GQ: Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U. J Org Chem. 2014 Jan 3;79(1):240-50. doi: 10.1021/jo402419h. Epub 2013 Dec 10. [PubMed:24299147 ]
Zangara A: The psychopharmacology of huperzine A: an alkaloid with cognitive enhancing and neuroprotective properties of interest in the treatment of Alzheimer's disease. Pharmacol Biochem Behav. 2003 Jun;75(3):675-86. doi: 10.1016/s0091-3057(03)00111-4. [PubMed:12895686 ]
Ishiuchi K, Park JJ, Long RM, Gang DR: Production of huperzine A and other Lycopodium alkaloids in Huperzia species grown under controlled conditions and in vitro. Phytochemistry. 2013 Jul;91:208-19. doi: 10.1016/j.phytochem.2012.11.012. Epub 2013 Jan 7. [PubMed:23306162 ]
Dong LH, Fan SW, Ling QZ, Huang BB, Wei ZJ: Indentification of huperzine A-producing endophytic fungi isolated from Huperzia serrata. World J Microbiol Biotechnol. 2014 Mar;30(3):1011-7. doi: 10.1007/s11274-013-1519-6. Epub 2013 Oct 16. [PubMed:24129696 ]
Sui X, Gao C: Huperzine A ameliorates damage induced by acute myocardial infarction in rats through antioxidant, anti-apoptotic and anti-inflammatory mechanisms. Int J Mol Med. 2014 Jan;33(1):227-33. doi: 10.3892/ijmm.2013.1546. Epub 2013 Nov 1. [PubMed:24190328 ]
LOTUS database [Link]

Showing NP-Card for (1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol (NP0246629)

MOL for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

3D MOL for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

3D SDF for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

3D-SDF for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

PDB for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

3D PDB for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

SMILES for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

INCHI for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

Structure for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

3D Structure for NP0246629 ((1r,9r,13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)