NP-MRD: Showing NP-Card for epinorlycoramine (NP0292982)

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Record Information

Version

2.0

Created at

2022-09-10 00:45:59 UTC

Updated at

2022-09-10 00:45:59 UTC

NP-MRD ID

NP0292982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epinorlycoramine

Description

Epinorlycoramine belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A. epinorlycoramine is found in Narcissus pseudonarcissus. Based on a literature review very few articles have been published on Epinorlycoramine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    4.8300   -1.7972   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4430   -1.7373   -0.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171   -0.6061   -0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3755    0.5905   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6279    1.7130    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2339    1.6381    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887    0.4359   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358   -0.6945   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -1.7858   -0.4367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8013   -1.2346   -0.7902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9019   -2.1787   -0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -2.0711    0.5445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1297   -2.3161    0.1973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507   -0.7705    1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -0.3551    1.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366    0.0144    0.0272 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6402    1.1134   -0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5947    2.3563    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320    3.2664   -0.2408 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655    2.9728    0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967   -0.9346   -1.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -2.7077   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2509   -1.9790    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    0.6309   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792    2.6825    0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6831   -0.9253   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4794   -3.2284   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495   -2.1463   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -2.8754    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2220   -2.2654   -0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3892   -0.0203    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1738   -0.9500    2.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    0.3728    2.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -1.2900    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185    1.3536   -1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6602    0.8025   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5899    2.8770    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886    2.1879    1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    3.0342   -1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171    3.7574    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4436    3.0698    1.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  8  3  1  0
  7  6  1  0
 10 16  1  0
  7 16  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
 20 40  1  0
 20 41  1  0
 19 39  1  0
 18 37  1  0
 18 38  1  0
 17 35  1  0
 17 36  1  0
 15 33  1  0
 15 34  1  0
 14 31  1  0
 14 32  1  0
 12 29  1  1
 13 30  1  0
 11 27  1  0
 11 28  1  0
 10 26  1  6
M  END


  Mrv1652309102202462D          

 20 23  0  0  1  0            999 V2000
    5.3571   -0.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2973    0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5974    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532    1.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2374    1.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907    0.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222    0.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1558    0.5519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3484    0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.9964    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0096    0.8267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    1.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8618    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124    1.3359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4157    2.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2186    3.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045    3.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  7  1  1  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2CNCC[C@@]34CC[C@@H](O)C[C@@H]3OC1=C24

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-3,11,13,17-18H,4-9H2,1H3/t11-,13+,16+/m1/s1

> <INCHI_KEY>
LBIHNERKYNXGRF-FFSVYQOJSA-N

> <FORMULA>
C16H21NO3

> <MOLECULAR_WEIGHT>
275.348

> <EXACT_MASS>
275.15214354

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.09882379742641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17)-trien-14-ol

> <JCHEM_LOGP>
0.986009063

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.17340966599853

> <JCHEM_PKA_STRONGEST_BASIC>
9.282837327408558

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
76.0476

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17)-trien-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.000  -1.088   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.494  -0.764   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.022   0.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.055   1.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.582   3.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.006   3.692   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.043   2.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.516   1.025   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.268   0.122   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.024   1.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.517   0.713   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.489   1.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.018   1.543   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.968   3.324   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.475   3.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.503   2.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.509   4.154   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.141   5.685   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       5.608   6.223   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.789   5.198   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   10   17                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    6                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO₃

Average Mass

275.3480 Da

Monoisotopic Mass

275.15214 Da

IUPAC Name

(1R,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17)-trien-14-ol

Traditional Name

(1R,12S,14R)-9-methoxy-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17)-trien-14-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CNCC[C@@]34CC[C@@H](O)C[C@@H]3OC1=C24

InChI Identifier

InChI=1S/C16H21NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-3,11,13,17-18H,4-9H2,1H3/t11-,13+,16+/m1/s1

InChI Key

LBIHNERKYNXGRF-FFSVYQOJSA-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
Narcissus pseudonarcissus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids with a structure characterized a tetracyclic skeleton with two ortho aromatic protons in ring A.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Galanthamine-type amaryllidaceae alkaloids

Direct Parent

Galanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Galanthamine-type amaryllidaceae alkaloid
Benzazepine
Coumaran
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Benzenoid
Cyclic alcohol
Secondary alcohol
Azacycle
Secondary amine
Ether
Secondary aliphatic amine
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzazepine (CHEBI:31544 )

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	0.99	ChemAxon
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.05 m³·mol⁻¹	ChemAxon
Polarizability	30.1 Å³	ChemAxon
Number of Rings	4	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

391834

KEGG Compound ID

C12234

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443724

PDB ID

Not Available

ChEBI ID

31544

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for epinorlycoramine (NP0292982)

MOL for NP0292982 (epinorlycoramine)

3D MOL for NP0292982 (epinorlycoramine)

3D SDF for NP0292982 (epinorlycoramine)

3D-SDF for NP0292982 (epinorlycoramine)

PDB for NP0292982 (epinorlycoramine)

3D PDB for NP0292982 (epinorlycoramine)

SMILES for NP0292982 (epinorlycoramine)

INCHI for NP0292982 (epinorlycoramine)

Structure for NP0292982 (epinorlycoramine)

3D Structure for NP0292982 (epinorlycoramine)