NP-MRD: Showing NP-Card for Narwedine (NP0050743)

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Record Information

Version

2.0

Created at

2022-04-27 22:04:49 UTC

Updated at

2022-04-27 22:04:49 UTC

NP-MRD ID

NP0050743

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Narwedine

Description

(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]Heptadeca-6(17),7,9,15-tetraen-14-one 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. Narwedine is found in Crinum amabile , Galanthus elwesii, Galanthus nivalis , Hippeastrum papilio, Leucojum aestivum , Lycoris guangxiensis, Narcissus pseudonarcissus subsp.pseudonarcissus, Ungernia severtzovii, Ungernia victoris and Ungernia vvedenskyi. Based on a literature review very few articles have been published on (1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0¹,¹².0⁶,¹⁷]Heptadeca-6(17),7,9,15-tetraen-14-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200042D          

 21 24  0  0  1  0            999 V2000
    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
    4.2973    0.3757    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
    3.9971   -1.0214    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
    2.4124    1.3359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5823    2.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574    2.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    3.3730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    2.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070    4.1890    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
    1.0544    1.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7978    0.9964    0.0000 C   0  0  0  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
    1.3484    0.3821    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  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11  4  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
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 14 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 10 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@@H]3CC(=O)C=C[C@@]33CCN(C)CC(C=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m1/s1

> <INCHI_KEY>
QENVUHCAYXAROT-RHSMWYFYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.343

> <EXACT_MASS>
285.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.289133682316397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-one

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.803082757666668

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.69016690239164

> <JCHEM_PKA_STRONGEST_BASIC>
7.90709582267951

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
81.29709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-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       9.055   1.843   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.582   3.309   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.006   3.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.043   2.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.516   1.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.022   0.701   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.494  -0.764   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.461  -1.907   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       4.503   2.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.820   4.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.401   5.591   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.759   6.296   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.885   5.194   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.986   7.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.475   3.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.968   3.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.489   1.860   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.018   1.543   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.517   0.713   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10    4   12   17                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14    3                                                       
CONECT   16   14                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3430 Da

Monoisotopic Mass

285.13649 Da

IUPAC Name

(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-one

Traditional Name

(1R,12R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-one

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@@H]3CC(=O)C=C[C@@]33CCN(C)CC(C=C1)=C23

InChI Identifier

InChI=1S/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m1/s1

InChI Key

QENVUHCAYXAROT-RHSMWYFYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Crinum amabile	Plant	KNApSAcK
Galanthus elwesii	Plant	KNApSAcK
Galanthus nivalis	Plant	KNApSAcK
Hippeastrum papilio	LOTUS Database	35616633
Leucojum aestivum	Plant	KNApSAcK
Lycoris guangxiensis	Plant	KNApSAcK
Narcissus pseudonarcissus subsp.pseudonarcissus	Plant	KNApSAcK
Ungernia severtzovii	Plant	KNApSAcK
Ungernia victoris	Plant	KNApSAcK
Ungernia vvedenskyi	Plant	KNApSAcK

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
Cyclohexenone
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Amine
Organic oxygen 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	2.1	ALOGPS
logP	1.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.3 m³·mol⁻¹	ChemAxon
Polarizability	30.29 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

390264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Narwedine (NP0050743)

MOL for NP0050743 (Narwedine)

3D MOL for NP0050743 (Narwedine)

3D SDF for NP0050743 (Narwedine)

3D-SDF for NP0050743 (Narwedine)

PDB for NP0050743 (Narwedine)

3D PDB for NP0050743 (Narwedine)

SMILES for NP0050743 (Narwedine)

INCHI for NP0050743 (Narwedine)

Structure for NP0050743 (Narwedine)

3D Structure for NP0050743 (Narwedine)