NP-MRD: Showing NP-Card for tuberostemonoxonine (NP0331800)

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Record Information

Version

2.0

Created at

2023-09-08 08:17:47 UTC

Updated at

2024-09-03 04:17:00 UTC

NP-MRD ID

NP0331800

Natural Product DOI

https://doi.org/10.57994/0886

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tuberostemonoxonine

Description

Tuberostemonoxonine belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. Based on a literature review very few articles have been published on tuberostemonoxonine.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09082308172D          

 33 38  0  0  1  0            999 V2000
    6.7559    0.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311    0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4352   -0.1288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6773   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6549    0.1389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7353   -0.6821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -0.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0864    0.0709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3523    0.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355   -0.5045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228   -1.2679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509   -2.0044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9636   -1.3387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281   -2.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -2.9517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7766   -3.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365   -2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -4.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119   -1.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -1.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -0.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.9590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8447    0.5061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164    1.4188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9117    2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    2.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684    0.9638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7698    1.7826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4571    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  1  0  0  0
 15 19  2  0  0  0  0
 11 20  1  6  0  0  0
 11 21  1  0  0  0  0
  7 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  7 27  1  1  0  0  0
 28 26  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 31 28  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END


  Mrv2104 09082308172D          

 33 38  0  0  1  0            999 V2000
    6.7559    0.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311    0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4352   -0.1288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6773   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6549    0.1389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7353   -0.6821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -0.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0864    0.0709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3523    0.4473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4355   -0.5045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228   -1.2679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4509   -2.0044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9636   -1.3387    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281   -2.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468   -3.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -2.9517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7766   -3.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6365   -2.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -4.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3119   -1.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -1.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -0.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    1.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761    0.9590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8447    0.5061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9164    1.4188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9117    2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    2.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684    0.9638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7698    1.7826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4571    1.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  1  0  0  0
 15 19  2  0  0  0  0
 11 20  1  6  0  0  0
 11 21  1  0  0  0  0
  7 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  0  0  0
  7 27  1  1  0  0  0
 28 26  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 31 28  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C[C@H](C)C(=O)O1)[C@]1([H])C[C@]23O[C@@]4(CCCCN1[C@]24O)[C@H](CC)[C@@]1([H])OC(=O)[C@@H](C)[C@@]31[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO6/c1-4-13-17-16(12(3)19(25)28-17)21-10-14(15-9-11(2)18(24)27-15)23-8-6-5-7-20(13,29-21)22(21,23)26/h11-17,26H,4-10H2,1-3H3/t11-,12-,13+,14-,15-,16+,17+,20-,21+,22+/m0/s1

> <INCHI_KEY>
CETDRLMCABPQMT-FXRLJSBFSA-N

> <FORMULA>
C22H31NO6

> <MOLECULAR_WEIGHT>
405.491

> <EXACT_MASS>
405.215137722

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.3136932649286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,9S,10R,11R,14S,15R,16R)-10-ethyl-16-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12,17-dioxa-4-azapentacyclo[7.6.1.1^{1,9}.0^{4,16}.0^{11,15}]heptadecan-13-one

> <JCHEM_LOGP>
2.2412309969999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.268411672222172

> <JCHEM_PKA_STRONGEST_BASIC>
8.17862062590563

> <JCHEM_POLAR_SURFACE_AREA>
85.30000000000001

> <JCHEM_REFRACTIVITY>
101.1189

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,9S,10R,11R,14S,15R,16R)-10-ethyl-16-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12,17-dioxa-4-azapentacyclo[7.6.1.1^{1,9}.0^{4,16}.0^{11,15}]heptadecan-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-23         0                                  
HETATM    1  O   UNK     0      12.611   0.965   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.071   0.990   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.146  -0.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.598  -1.713   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.689   0.259   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       8.839  -1.273   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       7.262  -0.569   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.761   0.132   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.391   0.835   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.546  -0.942   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.269  -2.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.575  -3.741   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       3.665  -2.499   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0       5.279  -5.111   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.194  -6.204   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.819  -5.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.450  -6.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.055  -3.988   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.440  -7.724   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       6.182  -3.607   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       6.821  -2.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.027  -0.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.563   1.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.226   2.536   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.759   2.871   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.929   1.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.177   0.945   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.311   2.649   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.302   4.188   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.631   4.966   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.714   1.799   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.904   3.327   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0      10.187   2.251   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   31                                             
CONECT    6    5                                                            
CONECT    7    5    8   21   27                                             
CONECT    8    7    9   10   26                                             
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12   20   21                                             
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12                                                       
CONECT   19   15                                                            
CONECT   20   11                                                            
CONECT   21   11    7                                                       
CONECT   22   10   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    8   27   28                                             
CONECT   27   26    7                                                       
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    5   32   33                                             
CONECT   32   31                                                            
CONECT   33   31    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₆

Average Mass

405.4910 Da

Monoisotopic Mass

405.21514 Da

IUPAC Name

(1R,3S,9S,10R,11R,14S,15R,16R)-10-ethyl-16-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12,17-dioxa-4-azapentacyclo[7.6.1.1^{1,9}.0^{4,16}.0^{11,15}]heptadecan-13-one

Traditional Name

(1R,3S,9S,10R,11R,14S,15R,16R)-10-ethyl-16-hydroxy-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12,17-dioxa-4-azapentacyclo[7.6.1.1^{1,9}.0^{4,16}.0^{11,15}]heptadecan-13-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(C[C@H](C)C(=O)O1)[C@]1([H])C[C@]23O[C@@]4(CCCCN1[C@]24O)[C@H](CC)[C@@]1([H])OC(=O)[C@@H](C)[C@@]31[H]

InChI Identifier

InChI=1S/C22H31NO6/c1-4-13-17-16(12(3)19(25)28-17)21-10-14(15-9-11(2)18(24)27-15)23-8-6-5-7-20(13,29-21)22(21,23)26/h11-17,26H,4-10H2,1-3H3/t11-,12-,13+,14-,15-,16+,17+,20-,21+,22+/m0/s1

InChI Key

CETDRLMCABPQMT-FXRLJSBFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-09-08	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Stenine backbone
Indole or derivatives
Fatty acid ester
Azepane
Para-oxazepine
Fatty acyl
N-alkylpyrrolidine
Oxane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Pyrrolidine
Cyclic alcohol
Oxetane
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	2.24	ChemAxon
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	8.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.12 m³·mol⁻¹	ChemAxon
Polarizability	43.31 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for tuberostemonoxonine (NP0331800)

MOL for NP0331800 (tuberostemonoxonine)

3D MOL for NP0331800 (tuberostemonoxonine)

3D SDF for NP0331800 (tuberostemonoxonine)

3D-SDF for NP0331800 (tuberostemonoxonine)

PDB for NP0331800 (tuberostemonoxonine)

3D PDB for NP0331800 (tuberostemonoxonine)

SMILES for NP0331800 (tuberostemonoxonine)

INCHI for NP0331800 (tuberostemonoxonine)

Structure for NP0331800 (tuberostemonoxonine)

3D Structure for NP0331800 (tuberostemonoxonine)