NP-MRD: Showing NP-Card for 1',2'-didehydrostemofoline (NP0221717)

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Record Information

Version

2.0

Created at

2022-09-05 23:22:01 UTC

Updated at

2022-09-05 23:22:01 UTC

NP-MRD ID

NP0221717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1',2'-didehydrostemofoline

Description

CHEBI:70413 Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. 1',2'-didehydrostemofoline is found in Stemona curtisii. Based on a literature review very few articles have been published on CHEBI:70413.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201222D          

 28 33  0  0  1  0            999 V2000
   -1.0554    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7184    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6151   -0.0014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0465    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648    0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9523    0.9929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5408    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -1.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -2.6344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -2.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528   -0.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993    0.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3735   -0.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    1.2771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795    1.4923    0.0000 N   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 22  1  0  0  0  0
 23 22  1  6  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  1  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  6  0  0  0
  5 28  1  0  0  0  0
M  END


  Mrv1652309062201222D          

 28 33  0  0  1  0            999 V2000
   -1.0554    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7184    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6151   -0.0014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0465    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648    0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9523    0.9929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5408    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -1.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -2.6344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -2.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528   -0.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993    0.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3735   -0.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    1.2771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795    1.4923    0.0000 N   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 22  1  0  0  0  0
 23 22  1  6  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  1  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  6  0  0  0
  5 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C\[C@@]12[C@@H]3C[C@H]4[C@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1\OC(=O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h6,8,11,13-16H,5,7,9-10H2,1-4H3/b8-6+,19-18-/t11-,13-,14+,15-,16+,21-,22+/m0/s1

> <INCHI_KEY>
XNUWGEPKIOWLHQ-KQYNXQAPSA-N

> <FORMULA>
C22H27NO5

> <MOLECULAR_WEIGHT>
385.46

> <EXACT_MASS>
385.188922973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.35765170623657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,3Z,4S,5R,6S,8S,9S,13R)-9-[(1E)-but-1-en-1-yl]-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.2818781396666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.233566538660716

> <JCHEM_POLAR_SURFACE_AREA>
57.23000000000001

> <JCHEM_REFRACTIVITY>
105.1721

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,3Z,4S,5R,6S,8S,9S,13R)-9-[(1E)-but-1-en-1-yl]-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.970   3.253   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.861   2.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.619   2.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.728   1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.208   1.968   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.015  -0.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953   0.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.481   1.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.382   1.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.378   1.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.476   2.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.200   0.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.434  -1.089   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.341  -2.173   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.035  -3.548   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.330  -4.918   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.557  -3.313   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.641  -4.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.804  -1.793   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.179  -1.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.265   0.438   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.440   2.086   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.391   0.579   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.431  -0.687   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.853   2.384   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   3.927   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.268   4.267   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.575   2.786   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25   28                                             
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   12   23                                                       
CONECT   23   22    9   24   25                                             
CONECT   24   23    6                                                       
CONECT   25   23    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    8    5                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₅

Average Mass

385.4600 Da

Monoisotopic Mass

385.18892 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC\C=C\[C@@]12[C@@H]3C[C@H]4[C@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1\OC(=O)C(C)=C1OC

InChI Identifier

InChI=1S/C22H27NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h6,8,11,13-16H,5,7,9-10H2,1-4H3/b8-6+,19-18-/t11-,13-,14+,15-,16+,21-,22+/m0/s1

InChI Key

XNUWGEPKIOWLHQ-KQYNXQAPSA-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
Stemona curtisii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Stemoamide backbone
Stemona alkaloid
Furopyran
Pyrrolizidine
Para-oxazepine
Ketal
Azepane
2-furanone
Oxane
Piperidine
Pyran
N-alkylpyrrolidine
Dihydrofuran
Enol ester
Furan
Vinylogous ester
Pyrrolidine
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Tertiary aliphatic amine
Lactone
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:70413 )

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

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

26625802

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56666692

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1',2'-didehydrostemofoline (NP0221717)

MOL for NP0221717 (1',2'-didehydrostemofoline)

3D MOL for NP0221717 (1',2'-didehydrostemofoline)

3D SDF for NP0221717 (1',2'-didehydrostemofoline)

3D-SDF for NP0221717 (1',2'-didehydrostemofoline)

PDB for NP0221717 (1',2'-didehydrostemofoline)

3D PDB for NP0221717 (1',2'-didehydrostemofoline)

SMILES for NP0221717 (1',2'-didehydrostemofoline)

INCHI for NP0221717 (1',2'-didehydrostemofoline)

Structure for NP0221717 (1',2'-didehydrostemofoline)

3D Structure for NP0221717 (1',2'-didehydrostemofoline)