NP-MRD: Showing NP-Card for (+)-Neostenine (NP0068686)

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Record Information

Version

2.0

Created at

2022-04-28 13:57:14 UTC

Updated at

2022-04-28 13:57:15 UTC

NP-MRD ID

NP0068686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Neostenine

Description

Neostenine belongs to the class of organic compounds known as stenine-type alkaloids. These are alkaloids which can be structurally represented by the tetracyclic\nfuro[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one nucleus. (+)-Neostenine is found in Stemona tuberosa . Based on a literature review very few articles have been published on Neostenine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
   -2.4072    2.8327   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905    2.1808   -0.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    1.5146    0.5604 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9400    0.9873    0.0853 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7210    0.5730    1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2184    0.8634    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5939    0.5346   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767   -0.8177   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415   -0.7578   -1.4186 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.0760   -1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2655   -2.3566   -0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -0.9897   -0.7058 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0388   -0.9210    0.6429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4437   -1.4119    0.6987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2703   -1.1482   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155   -0.5610    1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8137   -0.9463    2.6917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4749    0.6944    1.5354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0917    0.4287    1.2546 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7070   -0.0254   -0.9623 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3222    3.3039    0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326    2.1040   -0.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    3.6148   -0.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474    3.0073   -0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382    1.5507   -1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1479    2.3141    1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594    1.8699   -0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -0.4512    1.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983    1.2215    2.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7708    0.1712    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700    1.8888    1.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    1.2981   -1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155    0.4764   -0.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -1.4318    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7709   -1.3742   -1.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992   -2.1186   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2670   -2.8041   -1.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -2.8089    0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4143   -3.0686   -1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2164   -0.9627   -1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4575   -1.6514    1.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -2.4708    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9674   -1.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0235   -0.1641   -0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3302   -1.0656   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335    0.3495    2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3798    0.5712   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 20  1  0
  4  3  1  0
 13 19  1  0
 20 12  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  1
 19 46  1  1
 14 42  1  1
 15 43  1  0
 15 44  1  0
 15 45  1  0
 13 41  1  1
 12 40  1  6
 11 38  1  0
 11 39  1  0
 10 36  1  0
 10 37  1  0
  8 34  1  0
  8 35  1  0
  7 32  1  0
  7 33  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
  4 27  1  6
 20 47  1  6
M  END


  Mrv1652304282215572D          

 20 23  0  0  1  0            999 V2000
    1.0007   -0.5657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9662   -1.3900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3003   -1.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957   -1.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223   -0.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4336   -0.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -0.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996    0.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    0.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -0.1404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4294   -0.5399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4443   -1.3648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7374   -1.7901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7634   -2.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0623   -3.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7062   -0.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -0.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -0.2709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4500    0.5182    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  1  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  7  1  0  0  0  0
  1  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  1 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
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 12 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0068686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1[C@H]2OC(=O)[C@@H](C)[C@H]2[C@@H]2CCN3CCCC[C@H]1[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO2/c1-3-11-12-6-4-5-8-18-9-7-13(15(12)18)14-10(2)17(19)20-16(11)14/h10-16H,3-9H2,1-2H3/t10-,11+,12+,13-,14-,15+,16+/m0/s1

> <INCHI_KEY>
ROIHYOJMCBKEER-FGBMJVKNSA-N

> <FORMULA>
C17H27NO2

> <MOLECULAR_WEIGHT>
277.408

> <EXACT_MASS>
277.204179113

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
31.79134338907891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R,10R,11R,14S,15R,16R)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadecan-13-one

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.7810373076666663

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.922903957859932

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
78.24669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R,10R,11R,14S,15R,16R)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadecan-13-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       1.868  -1.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.804  -2.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.561  -3.504   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.925  -3.099   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.535  -1.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.809  -0.326   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.705  -0.046   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.306   1.372   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.840   1.238   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.187  -0.262   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.535  -1.008   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.563  -2.548   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.243  -3.342   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.292  -4.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.983  -5.692   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.036  -2.997   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.918  -1.735   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.458  -1.707   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.991  -0.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.440   0.967   0.000  0.00  0.00           C+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₇NO₂

Average Mass

277.4080 Da

Monoisotopic Mass

277.20418 Da

IUPAC Name

(1S,9R,10R,11R,14S,15R,16R)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadecan-13-one

Traditional Name

(1S,9R,10R,11R,14S,15R,16R)-10-ethyl-14-methyl-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadecan-13-one

CAS Registry Number

Not Available

SMILES

CC[C@H]1[C@H]2OC(=O)[C@@H](C)[C@H]2[C@@H]2CCN3CCCC[C@H]1[C@H]23

InChI Identifier

InChI=1S/C17H27NO2/c1-3-11-12-6-4-5-8-18-9-7-13(15(12)18)14-10(2)17(19)20-16(11)14/h10-16H,3-9H2,1-2H3/t10-,11+,12+,13-,14-,15+,16+/m0/s1

InChI Key

ROIHYOJMCBKEER-FGBMJVKNSA-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
Stemona tuberosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stenine-type alkaloids. These are alkaloids which can be structurally represented by the tetracyclic\nfuro[2,3-h]pyrrolo[3,2,1-jk][1]benzazepin-10(2H)-one nucleus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stenine-type alkaloids

Direct Parent

Stenine-type alkaloids

Alternative Parents

Substituents

Stenine backbone
Indole or derivatives
Azepane
Gamma butyrolactone
N-alkylpyrrolidine
Oxolane
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.75	ALOGPS
logP	2.78	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	11.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.25 m³·mol⁻¹	ChemAxon
Polarizability	31.79 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

C00026717

Chemspider ID

9711207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11536426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Neostenine (NP0068686)

MOL for NP0068686 ((+)-Neostenine)

3D MOL for NP0068686 ((+)-Neostenine)

3D SDF for NP0068686 ((+)-Neostenine)

3D-SDF for NP0068686 ((+)-Neostenine)

PDB for NP0068686 ((+)-Neostenine)

3D PDB for NP0068686 ((+)-Neostenine)

SMILES for NP0068686 ((+)-Neostenine)

INCHI for NP0068686 ((+)-Neostenine)

Structure for NP0068686 ((+)-Neostenine)

3D Structure for NP0068686 ((+)-Neostenine)