NP-MRD: Showing NP-Card for galanthan (NP0256948)

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Record Information

Version

2.0

Created at

2022-09-07 21:56:20 UTC

Updated at

2022-09-07 21:56:20 UTC

NP-MRD ID

NP0256948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

galanthan

Description

Galanthan belongs to the class of organic compounds known as amaryllidaceae alkaloids. These are isoquinoline alkaloids with a skeleton deriving from lycorine, norbelladine, homolycorine, hemanthamine, crinine, tazettine, montanine, plicamine, galanthindole, galanthamine, gracilline, among others. Amaryllidaceae Alkaloids represent a large group of biogenetically related isoquinoline alkaloids that are found exclusively in plants belonging to this family of Amaryllidaceae. This group of alkaloids is also derived from two tyrosine units which combine, with loss of one carbon atom, to give a benzylphenylethylamine precursor unit, e.G. Norbelladine, which by various oxidative cyclisation processes, prominent among which are phenol oxidative coupling reactions, can give rise to the nine major skeletal groups. galanthan is found in Clivia nobilis. galanthan was first documented in 2004 (PMID: 14987017). Based on a literature review a small amount of articles have been published on galanthan (PMID: 33751014) (PMID: 16826553).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
    4.1532    0.0594    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842    1.3364    0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382    1.6201    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476    0.6020   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924   -0.7129   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2454   -0.9400   -0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -1.8480   -0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395   -1.4236   -0.6240 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3498   -2.4022   -0.6046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977   -1.6009   -0.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -0.3345    0.3715 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5682    0.8954   -0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    2.1327    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286    1.9897    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129    0.8465   -0.1480 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6665   -0.4277    0.3755 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2107   -0.1035    0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.1564    0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9909    2.6445    0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -1.9470   -0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -2.5980    0.3822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3576   -2.3309   -1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -2.7892   -1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006   -3.2542    0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2913   -2.1726    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618   -1.3344   -1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -0.3139    1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6719    0.9571   -0.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    0.7945   -1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984    2.5271    1.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565    2.9390   -0.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0227    2.9516    0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4730    1.8180    1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415    0.9036   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362   -0.6403    1.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  6  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 16  1  0
 11 10  1  0
 16  8  1  0
  4  5  1  0
 16 15  1  0
 10 25  1  0
 10 26  1  0
  9 23  1  0
  9 24  1  0
  7 21  1  0
  7 22  1  0
  6 20  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
 15 34  1  6
 14 32  1  0
 14 33  1  0
 13 30  1  0
 13 31  1  0
 12 28  1  0
 12 29  1  0
 11 27  1  1
 16 35  1  1
M  END


  Mrv1652309072223562D          

 16 19  0  0  1  0            999 V2000
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  2  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16  8  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0256948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CN2CC3=CC=CC=C3[C@@H]3CCC[C@@H]1[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C15H19N/c1-2-6-13-12(4-1)10-16-9-8-11-5-3-7-14(13)15(11)16/h1-2,4,6,11,14-15H,3,5,7-10H2/t11-,14-,15+/m0/s1

> <INCHI_KEY>
CDIONMUWHFYLPO-TUKIKUTGSA-N

> <FORMULA>
C15H19N

> <MOLECULAR_WEIGHT>
213.324

> <EXACT_MASS>
213.151749616

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.427412537143127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,16R)-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6-triene

> <JCHEM_LOGP>
3.130884041

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.787995073130265

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
66.8635

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,16R)-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.120  -0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    4   16                                                  
CONECT   16   15   11    8                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉N

Average Mass

213.3240 Da

Monoisotopic Mass

213.15175 Da

IUPAC Name

(1S,12S,16R)-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6-triene

Traditional Name

(1S,12S,16R)-9-azatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-2,4,6-triene

CAS Registry Number

Not Available

SMILES

C1CN2CC3=CC=CC=C3[C@@H]3CCC[C@@H]1[C@@H]23

InChI Identifier

InChI=1S/C15H19N/c1-2-6-13-12(4-1)10-16-9-8-11-5-3-7-14(13)15(11)16/h1-2,4,6,11,14-15H,3,5,7-10H2/t11-,14-,15+/m0/s1

InChI Key

CDIONMUWHFYLPO-TUKIKUTGSA-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
Clivia nobilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amaryllidaceae alkaloids. These are isoquinoline alkaloids with a skeleton deriving from lycorine, norbelladine, homolycorine, hemanthamine, crinine, tazettine, montanine, plicamine, galanthindole, galanthamine, gracilline, among others. Amaryllidaceae Alkaloids represent a large group of biogenetically related isoquinoline alkaloids that are found exclusively in plants belonging to this family of Amaryllidaceae. This group of alkaloids is also derived from two tyrosine units which combine, with loss of one carbon atom, to give a benzylphenylethylamine precursor unit, e.G. Norbelladine, which by various oxidative cyclisation processes, prominent among which are phenol oxidative coupling reactions, can give rise to the nine major skeletal groups.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Not Available

Direct Parent

Amaryllidaceae alkaloids

Alternative Parents

Substituents

Galanthan skeleton
Amaryllidaceae alkaloid
Benzoquinoline
Phenanthridine
Quinoline
Tetrahydroisoquinoline
Indole or derivatives
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organopnictogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolizidine alkaloid (CHEBI:35646 )
indolizine alkaloid fundamental parent (CHEBI:35646 )

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	3.13	ChemAxon
pKa (Strongest Basic)	10.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.86 m³·mol⁻¹	ChemAxon
Polarizability	25.43 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

Not Available

Chemspider ID

5256836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6857500

PDB ID

Not Available

ChEBI ID

35646

Good Scents ID

Not Available

References

General References

Liang L, Li J, Shen B, Zhang Y, Liu J, Chen J, Liu D: The effect of carbonyl on the isomerization of a galanthan ring system and total synthesis of (+/-)-beta-lycorane. Org Biomol Chem. 2021 Mar 28;19(12):2767-2772. doi: 10.1039/d0ob02398a. Epub 2021 Mar 10. [PubMed:33751014 ]
Minter DE, Winslow CD, Watson WH, Bodige S: Structure elucidation of an unexpected product from dehydration of a beta-hydroxyketone. Magn Reson Chem. 2006 Oct;44(10):969-71. doi: 10.1002/mrc.1873. [PubMed:16826553 ]
Minter DE, Winslow CD: A photochemical approach to the Galanthan ring system. J Org Chem. 2004 Mar 5;69(5):1603-6. doi: 10.1021/jo0356560. [PubMed:14987017 ]
LOTUS database [Link]

Showing NP-Card for galanthan (NP0256948)

MOL for NP0256948 (galanthan)

3D MOL for NP0256948 (galanthan)

3D SDF for NP0256948 (galanthan)

3D-SDF for NP0256948 (galanthan)

PDB for NP0256948 (galanthan)

3D PDB for NP0256948 (galanthan)

SMILES for NP0256948 (galanthan)

INCHI for NP0256948 (galanthan)

Structure for NP0256948 (galanthan)

3D Structure for NP0256948 (galanthan)