NP-MRD: Showing NP-Card for 14-O-Acetylneoline (NP0069430)

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Record Information

Version

2.0

Created at

2022-04-28 14:46:32 UTC

Updated at

2022-04-28 14:46:33 UTC

NP-MRD ID

NP0069430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-O-Acetylneoline

Description

14-O-Acetylneoline is found in Aconitum carmichaeli , Brachycaudus aconiti Mordv. and Brachycaudus napelli Schrk..

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282216462D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  1  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 14 30  1  6  0  0  0
 31 12  1  1  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  1  0  0  0
  2 34  1  6  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1C[C@]23[C@@H]4[C@@H]5C[C@]67CC(=C)[C@H]([C@@H](O)[C@@H]26)[C@@H](O)[C@]7(OC(C)=O)[C@H]3N5C[C@]4(C)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H39NO8/c1-7-12(2)24(35)37-17-10-28-20-16-9-27-8-13(3)18(19(33)21(27)28)22(34)29(27,38-15(5)32)25(28)30(16)11-26(20,6)23(17)36-14(4)31/h12,16-23,25,33-34H,3,7-11H2,1-2,4-6H3/t12-,16?,17-,18-,19-,20-,21-,22-,23-,25+,26+,27-,28+,29+/m1/s1

> <INCHI_KEY>
QATQZHZBTQBUFQ-NBFUVAIPSA-N

> <FORMULA>
C29H39NO8

> <MOLECULAR_WEIGHT>
529.63

> <EXACT_MASS>
529.26756722

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.70697386060713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4,9-bis(acetyloxy)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
0.5145259003333323

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.641368065593014

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.498152023633757

> <JCHEM_PKA_STRONGEST_BASIC>
8.171265339699543

> <JCHEM_POLAR_SURFACE_AREA>
122.6

> <JCHEM_REFRACTIVITY>
132.01089999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4,9-bis(acetyloxy)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.597  -2.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.017  -2.711   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.571  -0.837   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.079  -2.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.970  -3.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.348  -0.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.918  -1.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.471  -0.749   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.794  -1.805   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.347  -3.607   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.063  -3.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.035  -1.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.590  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.752  -3.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.643  -4.510   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.645  -2.067   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.082  -0.582   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.436  -0.386   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.031   0.631   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.555   0.417   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.132  -1.011   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.504   1.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.927   3.058   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.029   1.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.977   2.629   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.174  -2.255   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.775  -3.672   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.304  -3.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.848  -4.902   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.944  -4.328   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.493  -0.326   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.858   0.241   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.619   1.763   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -0.963  -3.926   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.348  -4.296   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.539  -5.272   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.290  -6.792   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.980  -4.728   0.000  0.00  0.00           C+0
CONECT    1    2    7   11   35                                             
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1    8   31                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10    1   12                                                  
CONECT   12   11   13   18   31                                             
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16   30                                             
CONECT   15   14   10                                                       
CONECT   16   14   17   26                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   12                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   16   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   14                                                            
CONECT   31   12    7   32                                                  
CONECT   32   31    3   33                                                  
CONECT   33   32                                                            
CONECT   34    2                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₉NO₈

Average Mass

529.6300 Da

Monoisotopic Mass

529.26757 Da

IUPAC Name

(1S,3R,4S,5R,8S,9R,10R,11R,14R,16S,17S,18S,19S)-4,9-bis(acetyloxy)-10,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl (2R)-2-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1C[C@]23[C@@H]4[C@@H]5C[C@]67CC(=C)[C@H]([C@@H](O)[C@@H]26)[C@@H](O)[C@]7(OC(C)=O)[C@H]3N5C[C@]4(C)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C29H39NO8/c1-7-12(2)24(35)37-17-10-28-20-16-9-27-8-13(3)18(19(33)21(27)28)22(34)29(27,38-15(5)32)25(28)30(16)11-26(20,6)23(17)36-14(4)31/h12,16-23,25,33-34H,3,7-11H2,1-2,4-6H3/t12-,16?,17-,18-,19-,20-,21-,22-,23-,25+,26+,27-,28+,29+/m1/s1

InChI Key

QATQZHZBTQBUFQ-NBFUVAIPSA-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
Aconitum carmichaelii	Plant	KNApSAcK
Brachycaudus aconiti Mordv.	-	KNApSAcK
Brachycaudus napelli Schrk.	-	KNApSAcK

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	1.51	ALOGPS
logP	0.51	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	8.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.01 m³·mol⁻¹	ChemAxon
Polarizability	55.71 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for 14-O-Acetylneoline (NP0069430)

MOL for NP0069430 (14-O-Acetylneoline)

3D MOL for NP0069430 (14-O-Acetylneoline)

3D SDF for NP0069430 (14-O-Acetylneoline)

3D-SDF for NP0069430 (14-O-Acetylneoline)

PDB for NP0069430 (14-O-Acetylneoline)

3D PDB for NP0069430 (14-O-Acetylneoline)

SMILES for NP0069430 (14-O-Acetylneoline)

INCHI for NP0069430 (14-O-Acetylneoline)

Structure for NP0069430 (14-O-Acetylneoline)

3D Structure for NP0069430 (14-O-Acetylneoline)