NP-MRD: Showing NP-Card for Speciociliatine-N(4)-oxide (NP0331716)

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Record Information

Version

1.0

Created at

2023-07-13 15:44:12 UTC

Updated at

2024-05-12 18:38:52 UTC

NP-MRD ID

NP0331716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Speciociliatine-N(4)-oxide

Description

Based on a literature review very few articles have been published on Speciociliatine N-oxide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309282217262D          

 31 34  0  0  1  0            999 V2000
    6.3618   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2489    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8779    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.0141    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.4382   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    1.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  6 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  CHG  2  16   1  17  -1
M  END


  Mrv1652309282217262D          

 31 34  0  0  1  0            999 V2000
    6.3618   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7145   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2489    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8779    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595    3.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2672    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8909   -0.2772    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2619   -1.0141    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.4382   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1489    1.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262   -1.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  6 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
M  CHG  2  16   1  17  -1
M  END
> <DATABASE_ID>
NP0331716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@H]([C@H](CC)C[N+]1([O-])CCC1=C2NC2=CC=CC(OC)=C12)C(=C/OC)\C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O5/c1-5-14-12-25(27)10-9-15-21-18(7-6-8-20(21)29-3)24-22(15)19(25)11-16(14)17(13-28-2)23(26)30-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-,25?/m1/s1

> <INCHI_KEY>
KXNRITUKNSFMGJ-AFFTTWQFSA-N

> <FORMULA>
C23H30N2O5

> <MOLECULAR_WEIGHT>
414.502

> <EXACT_MASS>
414.215472074

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.150561059711464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,12bR)-2-[(1E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-methoxy-1H,2H,3H,4H,5H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-5-ium-5-olate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.175218403333332

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.24989171243993

> <JCHEM_PKA_STRONGEST_BASIC>
3.2275381583195775

> <JCHEM_POLAR_SURFACE_AREA>
83.61000000000001

> <JCHEM_REFRACTIVITY>
114.9581

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,12bR)-2-[(1E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-5-ium-5-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-SEP-22         0                                  
HETATM    1  C   UNK     0      11.875  -0.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.183   0.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.798   3.345   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.105   4.720   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.950   6.008   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.258   7.383   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.568   4.809   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.335   3.257   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.028   1.881   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.565   1.793   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       7.263  -0.517   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0       7.956  -1.893   0.000  0.00  0.00           O-1
HETATM   18  C   UNK     0       6.418  -1.805   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       5.878   2.234   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.480  -2.307   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.849  -3.012   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       4.070   2.147   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3   16                                                       
CONECT    5    3    6   14                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   20   21                                             
CONECT   16   15    4   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   22                                                       
CONECT   20   15                                                            
CONECT   21   15   22   31                                                  
CONECT   22   21   19   23                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   21                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀N₂O₅

Average Mass

414.5020 Da

Monoisotopic Mass

414.21547 Da

IUPAC Name

(2S,3S,12bR)-2-[(1E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-methoxy-1H,2H,3H,4H,5H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-5-ium-5-olate

Traditional Name

(2S,3S,12bR)-2-[(1E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-5-ium-5-olate

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@H]([C@H](CC)C[N+]1([O-])CCC1=C2NC2=CC=CC(OC)=C12)C(=C/OC)\C(=O)OC

InChI Identifier

InChI=1S/C23H30N2O5/c1-5-14-12-25(27)10-9-15-21-18(7-6-8-20(21)29-3)24-22(15)19(25)11-16(14)17(13-28-2)23(26)30-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19-,25?/m1/s1

InChI Key

KXNRITUKNSFMGJ-AFFTTWQFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
speciosa		Not Available

Chemical Taxonomy

Classification

Not classified

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	2.62	ALOGPS
logP	2.18	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	3.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.96 m³·mol⁻¹	ChemAxon
Polarizability	46.15 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	Yes	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

102497655

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Flores-Bocanegra L, Raja HA, Graf TN, Augustinovic M, Wallace ED, Hematian S, Kellogg JJ, Todd DA, Cech NB, Oberlies NH: The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids. J Nat Prod. 2020 Jul 24;83(7):2165-2177. doi: 10.1021/acs.jnatprod.0c00257. Epub 2020 Jun 29. [PubMed:32597657 ]

Showing NP-Card for Speciociliatine-N(4)-oxide (NP0331716)

MOL for NP0331716 (Speciociliatine-N(4)-oxide)

3D MOL for NP0331716 (Speciociliatine-N(4)-oxide)

3D SDF for NP0331716 (Speciociliatine-N(4)-oxide)

3D-SDF for NP0331716 (Speciociliatine-N(4)-oxide)

PDB for NP0331716 (Speciociliatine-N(4)-oxide)

3D PDB for NP0331716 (Speciociliatine-N(4)-oxide)

SMILES for NP0331716 (Speciociliatine-N(4)-oxide)

INCHI for NP0331716 (Speciociliatine-N(4)-oxide)

Structure for NP0331716 (Speciociliatine-N(4)-oxide)

3D Structure for NP0331716 (Speciociliatine-N(4)-oxide)