NP-MRD: Showing NP-Card for Diacetylveralkamine (NP0069808)

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Record Information

Version

2.0

Created at

2022-04-28 15:08:34 UTC

Updated at

2022-04-28 15:08:34 UTC

NP-MRD ID

NP0069808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diacetylveralkamine

Description

(1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-7,15-dien-13-yl acetate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. Diacetylveralkamine is found in Veratrum lobelianum . Based on a literature review very few articles have been published on (1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-7,15-dien-13-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217082D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282217082D          

 36 40  0  0  1  0            999 V2000
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    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155    1.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3604    2.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0462    2.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    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  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 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
 20 25  1  0  0  0  0
 23 26  1  6  0  0  0
 19 27  1  1  0  0  0
 18 28  1  1  0  0  0
 17 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  2 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@@H]1CC[C@H](C)CN1)[C@]1(C)[C@H](C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC=C12)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H47NO4/c1-18-7-12-28(32-17-18)19(2)31(6)27-11-10-26-24(25(27)16-29(31)36-21(4)34)9-8-22-15-23(35-20(3)33)13-14-30(22,26)5/h8,11,18-19,23-26,28-29,32H,7,9-10,12-17H2,1-6H3/t18-,19+,23-,24-,25-,26-,28-,29-,30-,31-/m0/s1

> <INCHI_KEY>
PSTOSWDMEJBSOY-TVVKNRCVSA-N

> <FORMULA>
C31H47NO4

> <MOLECULAR_WEIGHT>
497.72

> <EXACT_MASS>
497.350508997

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.11851382732223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,15-dien-13-yl acetate

> <ALOGPS_LOGP>
5.84

> <JCHEM_LOGP>
4.535535284999998

> <ALOGPS_LOGS>
-5.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.92989697881933

> <JCHEM_POLAR_SURFACE_AREA>
64.63

> <JCHEM_REFRACTIVITY>
142.89999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,15-dien-13-yl acetate

> <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      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.503  -0.859   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.308  -2.387   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.534  -3.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.339  -4.847   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.919  -5.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.307  -4.510   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -0.112  -2.982   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       0.724  -6.970   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.277   0.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.697  -1.787   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.776   3.254   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.673   3.777   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.953   4.247   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   14   19   28                                             
CONECT   19   18   20   27                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   23                                                            
CONECT   27   19                                                            
CONECT   28   18                                                            
CONECT   29   17   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,10R,11S,13S,14S)-5-(Acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0,.0,]heptadeca-7,15-dien-13-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₇NO₄

Average Mass

497.7200 Da

Monoisotopic Mass

497.35051 Da

IUPAC Name

(1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,15-dien-13-yl acetate

Traditional Name

(1S,2R,5S,10R,11S,13S,14S)-5-(acetyloxy)-2,14-dimethyl-14-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,15-dien-13-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]([C@@H]1CC[C@H](C)CN1)[C@]1(C)[C@H](C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC=C12)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C31H47NO4/c1-18-7-12-28(32-17-18)19(2)31(6)27-11-10-26-24(25(27)16-29(31)36-21(4)34)9-8-22-15-23(35-20(3)33)13-14-30(22,26)5/h8,11,18-19,23-26,28-29,32H,7,9-10,12-17H2,1-6H3/t18-,19+,23-,24-,25-,26-,28-,29-,30-,31-/m0/s1

InChI Key

PSTOSWDMEJBSOY-TVVKNRCVSA-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
Veratrum lobelianum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Delta-5-steroid
Piperidine
Dicarboxylic acid or derivatives
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	5.84	ALOGPS
logP	4.54	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	10.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	142.9 m³·mol⁻¹	ChemAxon
Polarizability	59.12 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

163105568

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Diacetylveralkamine (NP0069808)

MOL for NP0069808 (Diacetylveralkamine)

3D MOL for NP0069808 (Diacetylveralkamine)

3D SDF for NP0069808 (Diacetylveralkamine)

3D-SDF for NP0069808 (Diacetylveralkamine)

PDB for NP0069808 (Diacetylveralkamine)

3D PDB for NP0069808 (Diacetylveralkamine)

SMILES for NP0069808 (Diacetylveralkamine)

INCHI for NP0069808 (Diacetylveralkamine)

Structure for NP0069808 (Diacetylveralkamine)

3D Structure for NP0069808 (Diacetylveralkamine)