NP-MRD: Showing NP-Card for Auriculine (NP0051155)

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Record Information

Version

2.0

Created at

2022-04-27 22:33:57 UTC

Updated at

2022-04-27 22:33:58 UTC

NP-MRD ID

NP0051155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Auriculine

Description

[(1S,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Auriculine is found in Liparis auriculata and Liparis loeselii. Based on a literature review very few articles have been published on [(1S,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200332D          

 40 43  0  0  1  0            999 V2000
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  1 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282200332D          

 40 43  0  0  1  0            999 V2000
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   -2.4209   -1.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180   -0.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5447   -3.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968   -3.1487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9037   -3.3202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4558   -2.7071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2008   -1.9225    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3939   -1.7509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8418   -2.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1389   -0.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6910   -0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7529   -1.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2627   -2.8786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1587   -4.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4407   -4.9879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2476   -5.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5026   -5.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3096   -6.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9505   -6.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    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
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 13 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 25 30  1  1  0  0  0
 24 31  1  1  0  0  0
 23 32  1  1  0  0  0
 12 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@@H]1O)C(=O)OC[C@H]1CCN2CCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C31H45NO8/c1-18(2)7-9-20-14-23(30(37)38-17-22-11-13-32-12-5-6-24(22)32)15-21(10-8-19(3)4)29(20)40-31-28(36)27(35)26(34)25(16-33)39-31/h7-8,14-15,22,24-28,31,33-36H,5-6,9-13,16-17H2,1-4H3/t22-,24-,25-,26+,27+,28+,31+/m1/s1

> <INCHI_KEY>
FQXZITIIHQHGBC-KFPGTZKXSA-N

> <FORMULA>
C31H45NO8

> <MOLECULAR_WEIGHT>
559.7

> <EXACT_MASS>
559.314517413

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
61.99876600074819

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.4121828379999983

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.196469638283695

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.203779060996307

> <JCHEM_PKA_STRONGEST_BASIC>
10.17070859722552

> <JCHEM_POLAR_SURFACE_AREA>
128.92000000000002

> <JCHEM_REFRACTIVITY>
153.47469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7aR)-hexahydro-1H-pyrrolizin-1-ylmethyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

> <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       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.476  -3.956   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.982  -4.277   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.458  -5.741   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.428  -6.886   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.964  -6.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.440  -7.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.947  -7.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.977  -6.702   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.501  -5.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.995  -4.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.532  -4.093   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.056  -2.628   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.550  -2.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.519  -3.452   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.074  -0.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.484  -7.022   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -9.514  -5.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.020  -6.198   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.051  -5.053   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.575  -3.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.069  -3.268   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -9.038  -4.413   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.593  -1.804   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.623  -0.659   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -12.605  -2.444   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -13.557  -5.373   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -11.496  -7.662   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.423  -9.311   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.929  -9.631   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.405 -11.096   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.911 -11.416   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.374 -12.240   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
CONECT    1    2    5   40                                                  
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   13   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
CONECT   33   12   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    2   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39    1                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
[(1S,7AR)-hexahydro-1H-pyrrolizin-1-yl]methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid	Generator

Chemical Formula

C₃₁H₄₅NO₈

Average Mass

559.7000 Da

Monoisotopic Mass

559.31452 Da

IUPAC Name

[(1S,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

Traditional Name

(1S,7aR)-hexahydro-1H-pyrrolizin-1-ylmethyl 3,5-bis(3-methylbut-2-en-1-yl)-4-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@@H]1O)C(=O)OC[C@H]1CCN2CCC[C@H]12

InChI Identifier

InChI=1S/C31H45NO8/c1-18(2)7-9-20-14-23(30(37)38-17-22-11-13-32-12-5-6-24(22)32)15-21(10-8-19(3)4)29(20)40-31-28(36)27(35)26(34)25(16-33)39-31/h7-8,14-15,22,24-28,31,33-36H,5-6,9-13,16-17H2,1-4H3/t22-,24-,25-,26+,27+,28+,31+/m1/s1

InChI Key

FQXZITIIHQHGBC-KFPGTZKXSA-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
Liparis auriculata	Plant	KNApSAcK
Liparis loeselii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Pyrrolizidine
Phenol ether
Benzoyl
Sugar acid
Benzenoid
N-alkylpyrrolidine
Oxane
Monosaccharide
Monocyclic benzene moiety
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.61	ALOGPS
logP	3.41	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	10.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.92 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	153.47 m³·mol⁻¹	ChemAxon
Polarizability	62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

162964508

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Auriculine (NP0051155)

MOL for NP0051155 (Auriculine)

3D MOL for NP0051155 (Auriculine)

3D SDF for NP0051155 (Auriculine)

3D-SDF for NP0051155 (Auriculine)

PDB for NP0051155 (Auriculine)

3D PDB for NP0051155 (Auriculine)

SMILES for NP0051155 (Auriculine)

INCHI for NP0051155 (Auriculine)

Structure for NP0051155 (Auriculine)

3D Structure for NP0051155 (Auriculine)