NP-MRD: Showing NP-Card for (13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol (NP0311971)

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Record Information

Version

2.0

Created at

2022-09-11 08:20:56 UTC

Updated at

2022-09-11 08:20:57 UTC

NP-MRD ID

NP0311971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(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 Huperzia selago, Huperzia serrata, Lycopodiastrum casuarinoides, Phlegmariurus varius and Streptomyces coelicoflavus. (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 1987 (PMID: 3452958).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.1933   -1.7668    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610   -1.2995   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416   -0.5464   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0510   -0.1918    1.2626 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9181    1.2901    1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5808    2.0415    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139    3.5009    0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580    1.5052   -1.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.0043   -1.0985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4823   -0.4972   -2.4206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -0.4458   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.4990   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3927   -0.8961   -1.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -1.2209    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992   -1.5886    0.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5459   -1.1675    1.1234 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3050   -0.7773    0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2479   -0.7487    1.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.9517    1.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -2.3503   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7146   -2.4696    1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3960   -1.5596   -1.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8619   -0.5455    1.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1120    1.7652    2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3344    4.0294    0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036    3.8486   -0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    3.7590    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    1.9914   -1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2372    1.7627   -1.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2660   -1.5038   -2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228    0.0639   -3.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -0.2330   -2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334   -0.9525   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974   -1.4240    2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124   -0.1277    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1219   -1.7902    2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4 18  1  0
 18 17  1  0
 17 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 11  9  1  0
  9 10  1  6
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  9  3  1  0
  5  4  1  0
 16 17  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  1
 18 35  1  0
 18 36  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
 10 30  1  0
 10 31  1  0
  8 28  1  0
  8 29  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  5 24  1  0
M  END


  Mrv0541 02231217582D          

 18 20  0  0  1  0            999 V2000
    1.5842   -2.6685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -1.0121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1469   -1.3842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614   -0.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9664    0.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1117   -1.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455   -1.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9047   -0.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8218   -0.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7274   -0.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9869    1.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6443   -2.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924   -0.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806   -2.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2268   -2.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829    2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2  4  1  0  0  0  0
  3 10  1  0  0  0  0
  3 17  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 15  1  0  0  0  0
 13 18  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311971

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1/C2CC3=C(C=CC(=O)N3)C1(N)CC(C)=C2

> <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+

> <INCHI_KEY>
ZRJBHWIHUMBLCN-QDEBKDIKSA-N

> <FORMULA>
C15H18N2O

> <MOLECULAR_WEIGHT>
242.3162

> <EXACT_MASS>
242.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.850622799306638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(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>
75.795

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
huperzine A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       2.957  -4.981   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.505  -1.889   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.008  -2.584   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.888  -0.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.271   0.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.181   2.420   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.409  -2.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.618  -2.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.422  -0.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.267  -1.698   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.558  -1.075   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.028   0.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.442   3.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.803  -3.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.986  -1.458   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.564  -4.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.157  -4.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.181   4.981   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    4                                                            
CONECT    3   10   17                                                       
CONECT    4    2    6    7    8                                             
CONECT    5    6    9   12                                                  
CONECT    6    4    5   13                                                  
CONECT    7    4   11                                                       
CONECT    8    4   10   14                                                  
CONECT    9    5   10                                                       
CONECT   10    3    8    9                                                  
CONECT   11    7   12   15                                                  
CONECT   12    5   11                                                       
CONECT   13    6   18                                                       
CONECT   14    8   16                                                       
CONECT   15   11                                                            
CONECT   16   14   17                                                       
CONECT   17    1    3   16                                                  
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₁₈N₂O

Average Mass

242.3162 Da

Monoisotopic Mass

242.14191 Da

IUPAC Name

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

Traditional Name

huperzine A

CAS Registry Number

Not Available

SMILES

C\C=C1/C2CC3=C(C=CC(=O)N3)C1(N)CC(C)=C2

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+

InChI Key

ZRJBHWIHUMBLCN-QDEBKDIKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Huperzia selago	LOTUS Database	35616633
Huperzia serrata	LOTUS Database	35616633
Lycopodiastrum casuarinoides	LOTUS Database	35616633
Phlegmariurus varius	LOTUS Database	35616633
Streptomyces coelicoflavus	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities known as quinolones and derivatives. These are compounds containing a quinoline moiety which bears a ketone group.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Quinolines 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

Not Available

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	26.85 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

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

5912039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen SM, Xue ZG: [The effect of fordine on learning and memory in rats]. Yao Xue Xue Bao. 1987 Nov;22(11):801-6. [PubMed:3452958 ]
LOTUS database [Link]

Showing NP-Card for (13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol (NP0311971)

MOL for NP0311971 ((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 NP0311971 ((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 NP0311971 ((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 NP0311971 ((13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

PDB for NP0311971 ((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 NP0311971 ((13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

SMILES for NP0311971 ((13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

INCHI for NP0311971 ((13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)

Structure for NP0311971 ((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 NP0311971 ((13e)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6,10-tetraen-5-ol)