NP-MRD: Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate (NP0226976)

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Record Information

Version

2.0

Created at

2022-09-06 06:10:34 UTC

Updated at

2022-09-06 06:10:34 UTC

NP-MRD ID

NP0226976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate

Description

(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(acetyloxy)-2-hydroxy-2-(propan-2-yl)butanoate belongs to the class of organic compounds known as pyrrolizidines. hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate is found in Heliotropium floridum. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom (hexahydro-1H-pyrrolizin-1-yl)methyl 3-(acetyloxy)-2-hydroxy-2-(propan-2-yl)butanoate is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231514402D          

 23 24  0  0  0  0            999 V2000
   -1.8104   -1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258   -2.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4127   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -2.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6827   -3.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -3.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -2.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -3.7908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -3.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -4.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -3.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -3.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)(C(C)OC(C)=O)C(=O)OCC1CCN2CCCC12

> <INCHI_IDENTIFIER>
InChI=1S/C17H29NO5/c1-11(2)17(21,12(3)23-13(4)19)16(20)22-10-14-7-9-18-8-5-6-15(14)18/h11-12,14-15,21H,5-10H2,1-4H3

> <INCHI_KEY>
OPIPQZJQFXCYJD-UHFFFAOYSA-N

> <FORMULA>
C17H29NO5

> <MOLECULAR_WEIGHT>
327.421

> <EXACT_MASS>
327.204573038

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.7913234584421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(hexahydro-1H-pyrrolizin-1-yl)methyl 3-(acetyloxy)-2-hydroxy-2-(propan-2-yl)butanoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.1191051520054436

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.343659046513073

> <JCHEM_PKA_STRONGEST_BASIC>
10.166589855174928

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
85.2123

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexahydro-1H-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -3.379  -3.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.915  -3.785   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -2.755   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.595  -5.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.274  -6.798   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.101  -5.612   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.131  -4.467   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.577  -7.076   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.083  -7.396   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.559  -8.861   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.114  -6.252   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.942  -6.116   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   12                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   19                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(Hexahydro-1H-pyrrolizin-1-yl)methyl 3-(acetyloxy)-2-hydroxy-2-(propan-2-yl)butanoic acid	Generator

Chemical Formula

C₁₇H₂₉NO₅

Average Mass

327.4210 Da

Monoisotopic Mass

327.20457 Da

IUPAC Name

(hexahydro-1H-pyrrolizin-1-yl)methyl 3-(acetyloxy)-2-hydroxy-2-(propan-2-yl)butanoate

Traditional Name

hexahydro-1H-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(O)(C(C)OC(C)=O)C(=O)OCC1CCN2CCCC12

InChI Identifier

InChI=1S/C17H29NO5/c1-11(2)17(21,12(3)23-13(4)19)16(20)22-10-14-7-9-18-8-5-6-15(14)18/h11-12,14-15,21H,5-10H2,1-4H3

InChI Key

OPIPQZJQFXCYJD-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Heliotropium floridum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Fatty acid ester
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Fatty acyl
Pyrrolidine
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Alcohol
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	1.69	ALOGPS
logP	1.12	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.21 m³·mol⁻¹	ChemAxon
Polarizability	35.79 Å³	ChemAxon
Number of Rings	2	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

85274135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate (NP0226976)

MOL for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

3D MOL for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

3D SDF for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

3D-SDF for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

PDB for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

3D PDB for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

SMILES for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

INCHI for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

Structure for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)

3D Structure for NP0226976 (hexahydro-1h-pyrrolizin-1-ylmethyl 3-(acetyloxy)-2-hydroxy-2-isopropylbutanoate)