NP-MRD: Showing NP-Card for Fawcettidine (NP0051041)

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Record Information

Version

2.0

Created at

2022-04-27 22:29:22 UTC

Updated at

2022-04-27 22:29:22 UTC

NP-MRD ID

NP0051041

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fawcettidine

Description

Fawcettidine belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Fawcettidine is found in Huperzia serrata, Lycopodiella alopecuroides, Lycopodium clavatum, Lycopodium fawcettii, Lycopodium japonicum, Lycopoidium alopecuroides and Lycopodium phlegmaria. Fawcettidine was first documented in 2013 (PMID: 24188014). Based on a literature review a small amount of articles have been published on Fawcettidine (PMID: 28738241) (PMID: 33891425) (PMID: 29923424) (PMID: 24000162).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    3.5580   -1.6982   -0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753   -0.6758   -0.5096 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1524   -1.2843   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0335   -0.8019   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3244   -1.2440   -0.1963 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769   -1.2810   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    0.1407   -1.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1969    1.1004   -0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8719    1.4981   -0.2946 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0706    1.9791   -1.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    2.0629   -2.5445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    2.3419   -0.5491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2882    1.2789    0.5295 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5281    0.4736    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097    0.5605    0.4779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5449    0.3674    1.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2748   -0.8572    2.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9210   -1.6481    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960   -1.2673    0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908   -2.2132   -1.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420   -2.4828    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -0.2889   -1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822   -2.2977   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3175   -2.0622   -1.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867   -1.3948   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4269    0.2300   -2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690    0.1215   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    2.0496   -0.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7704    0.7610    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    2.3975    0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0766    3.3497   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2020    2.3142   -1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4172    1.8672    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3852    1.1198    0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379    0.0782    1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    0.5087    2.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799    1.2784    2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575   -0.6004    2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -1.5490    2.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.7272    1.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146   -1.5053    1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 18  1  0
 18 17  1  0
 17 16  1  0
 15 16  1  1
 15  4  1  0
  4  3  2  0
  3  2  1  0
 15 13  1  0
 15  9  1  0
  4  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
 14 34  1  0
 14 35  1  0
 13 33  1  1
 12 31  1  0
 12 32  1  0
  9 30  1  1
  8 28  1  0
  8 29  1  0
  7 26  1  0
  7 27  1  0
  6 24  1  0
  6 25  1  0
 18 40  1  0
 18 41  1  0
 17 38  1  0
 17 39  1  0
 16 36  1  0
 16 37  1  0
  3 23  1  0
M  END


  Mrv1652304282200292D          

 18 21  0  0  1  0            999 V2000
    1.4203   -0.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6975   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    0.0148    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0087    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315    1.2373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4373    0.8102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0370    1.5378    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8931    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -0.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0546   -0.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489   -0.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659    0.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601    1.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417    2.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    2.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9196    2.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7312   -0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  1  0  0  0
  6  7  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
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 17  1  1  0  0  0
  3 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051041

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2CC(=O)[C@H]3CCCN4CCC[C@]23C4=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO/c1-11-8-12-10-14(18)13-4-2-6-17-7-3-5-16(12,13)15(17)9-11/h9,11-13H,2-8,10H2,1H3/t11-,12+,13-,16+/m1/s1

> <INCHI_KEY>
ANHVSCXCALAIQN-IATRGZMQSA-N

> <FORMULA>
C16H23NO

> <MOLECULAR_WEIGHT>
245.366

> <EXACT_MASS>
245.177964365

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.896844967831377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,6S,9S)-4-methyl-13-azatetracyclo[7.7.0.0^{1,6}.0^{2,13}]hexadec-2-en-8-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
2.260878142666666

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.256669744972868

> <JCHEM_PKA_STRONGEST_BASIC>
9.338932979656787

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
74.21610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,6S,9S)-4-methyl-13-azatetracyclo[7.7.0.0^{1,6}.0^{2,13}]hexadec-2-en-8-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.651  -0.027   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.302  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.016   0.028   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.016   1.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.365   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.683   1.512   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802   2.870   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.400   2.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.040   0.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.343  -0.700   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.835  -1.012   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.318  -0.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.350   1.457   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.032   2.255   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.251   3.938   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.038   5.262   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.717   3.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.365  -0.715   0.000  0.00  0.00           C+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7   14                                             
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    1   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6                                                       
CONECT   15    7   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5                                                       
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
Fawcettimine	MeSH

Chemical Formula

C₁₆H₂₃NO

Average Mass

245.3660 Da

Monoisotopic Mass

245.17796 Da

IUPAC Name

(1S,4R,6S,9S)-4-methyl-13-azatetracyclo[7.7.0.0^{1,6}.0^{2,13}]hexadec-2-en-8-one

Traditional Name

(1S,4R,6S,9S)-4-methyl-13-azatetracyclo[7.7.0.0^{1,6}.0^{2,13}]hexadec-2-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2CC(=O)[C@H]3CCCN4CCC[C@]23C4=C1

InChI Identifier

InChI=1S/C16H23NO/c1-11-8-12-10-14(18)13-4-2-6-17-7-3-5-16(12,13)15(17)9-11/h9,11-13H,2-8,10H2,1H3/t11-,12+,13-,16+/m1/s1

InChI Key

ANHVSCXCALAIQN-IATRGZMQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 serrata	LOTUS Database	35616633
Lycopodiella alopecuroides	LOTUS Database	35616633
Lycopodium clavatum	LOTUS Database	35616633
Lycopodium fawcettii	Plant	KNApSAcK
Lycopodium japonicum	LOTUS Database	35616633
Lycopoidium alopecuroides	-	KNApSAcK
Phlegmariurus phlegmaria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Azepane
Piperidine
Ketone
Tertiary aliphatic amine
Tertiary amine
Enamine
Azacycle
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azaspiro compound (CHEBI:4988 )

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	3.15	ALOGPS
logP	2.26	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	19.26	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.22 m³·mol⁻¹	ChemAxon
Polarizability	27.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00001936

Chemspider ID

390907

KEGG Compound ID

C09862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang Y, Xiong J, Zou Y, Wang W, Huang C, Zhang HY, Hu JF: Annotinolide F and lycoannotines A-I, further Lycopodium alkaloids from Lycopodium annotinum. Phytochemistry. 2017 Nov;143:1-11. doi: 10.1016/j.phytochem.2017.07.003. Epub 2017 Jul 21. [PubMed:28738241 ]
Zeng C, Zheng C, Zhao J, Zhao G: Divergent total syntheses of (-)-lycopladine D, (+)-fawcettidine, and (+)-lycoposerramine Q. Org Lett. 2013 Nov 15;15(22):5846-9. doi: 10.1021/ol402906y. Epub 2013 Nov 4. [PubMed:24188014 ]
Zhong LR, Huang BB, Yang XL, Wang S, Yao ZJ: Concise Unified Access to (-)-8-Deoxy-13-dehydroserratinine, (+)-Fawcettimine, (+)-Fawcettidine, and (-)-8-Deoxyserratinine Using a Direct Intramolecular Reductive Coupling. Org Lett. 2021 May 7;23(9):3578-3583. doi: 10.1021/acs.orglett.1c00977. Epub 2021 Apr 23. [PubMed:33891425 ]
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Showing NP-Card for Fawcettidine (NP0051041)

MOL for NP0051041 (Fawcettidine)

3D MOL for NP0051041 (Fawcettidine)

3D SDF for NP0051041 (Fawcettidine)

3D-SDF for NP0051041 (Fawcettidine)

PDB for NP0051041 (Fawcettidine)

3D PDB for NP0051041 (Fawcettidine)

SMILES for NP0051041 (Fawcettidine)

INCHI for NP0051041 (Fawcettidine)

Structure for NP0051041 (Fawcettidine)

3D Structure for NP0051041 (Fawcettidine)