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Showing NP-Card for (7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate (NP0221302)

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Record Information
Version2.0
Created at2022-09-05 22:50:43 UTC
Updated at2022-09-05 22:50:43 UTC
NP-MRD IDNP0221302
Secondary Accession NumbersNone
Natural Product Identification
Common Name(7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate
Description(7A-methyl-hexahydro-1H-pyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. (7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate is found in Liparis cordifolia. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group (7a-methyl-hexahydro-1H-pyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate is a very strong basic compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)


  Mrv1533004171513242D          

 27 29  0  0  0  0            999 V2000
   -3.5723   -1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.7800    0.0000 O   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
   -1.4063   -2.2216    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
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -4.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -5.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -6.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400   -5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -3.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -3.3493    0.0000 O   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
    2.0542   -1.4924    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
Download

3D MOL for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)

Download
3D SDF for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)

  Mrv1533004171513242D          

 27 29  0  0  0  0            999 V2000
   -3.5723   -1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653   -1.7800    0.0000 O   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
   -1.4063   -2.2216    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
   -1.1092   -3.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -4.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -5.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810   -6.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0400   -5.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4682   -3.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2752   -3.3493    0.0000 O   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
    2.0542   -1.4924    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(CC=C(C)C)=C1O)C(=O)OCC1CCN2CCCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO4/c1-15(2)6-7-16-12-17(13-19(26-4)20(16)24)21(25)27-14-18-8-11-23-10-5-9-22(18,23)3/h6,12-13,18,24H,5,7-11,14H2,1-4H3

> <INCHI_KEY>
IYWSIDKNUJVAFH-UHFFFAOYSA-N

> <FORMULA>
C22H31NO4

> <MOLECULAR_WEIGHT>
373.493

> <EXACT_MASS>
373.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.27768930891698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7a-methyl-hexahydro-1H-pyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
2.790097892158523

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.771201676197734

> <JCHEM_PKA_STRONGEST_BASIC>
10.502830855144843

> <JCHEM_POLAR_SURFACE_AREA>
59.00000000000001

> <JCHEM_REFRACTIVITY>
108.18889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)
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PDB for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -6.668  -3.643   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.162  -3.323   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.131  -4.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.625  -4.147   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.595  -5.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.577  -7.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.053  -8.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.559  -8.861   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.035 -10.326   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.005 -11.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.541 -10.646   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.607  -5.932   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.114  -6.252   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.942  -6.116   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.834  -2.786   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7    3   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   19   22   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Download
3D PDB for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)
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SMILES for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)
COC1=CC(=CC(CC=C(C)C)=C1O)C(=O)OCC1CCN2CCCC12C
Download
INCHI for NP0221302 ((7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate)
InChI=1S/C22H31NO4/c1-15(2)6-7-16-12-17(13-19(26-4)20(16)24)21(25)27-14-18-8-11-23-10-5-9-22(18,23)3/h6,12-13,18,24H,5,7-11,14H2,1-4H3
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View in JSmol
Synonyms
ValueSource
(7a-Methyl-hexahydro-1H-pyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoic acidGenerator
Chemical FormulaC22H31NO4
Average Mass373.4930 Da
Monoisotopic Mass373.22531 Da
IUPAC Name(7a-methyl-hexahydro-1H-pyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate
Traditional Name(7a-methyl-hexahydropyrrolizin-1-yl)methyl 4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)benzoate
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(CC=C(C)C)=C1O)C(=O)OCC1CCN2CCCC12C
InChI Identifier
InChI=1S/C22H31NO4/c1-15(2)6-7-16-12-17(13-19(26-4)20(16)24)21(25)27-14-18-8-11-23-10-5-9-22(18,23)3/h6,12-13,18,24H,5,7-11,14H2,1-4H3
InChI KeyIYWSIDKNUJVAFH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Liparis cordifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids  in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzoic acids and derivatives  
Direct ParentM-methoxybenzoic acids and derivatives  
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • M-methoxybenzoic acid or derivatives
    • 

  • Benzoate ester
    • 

  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Benzoyl
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Pyrrolizidine
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • N-alkylpyrrolidine
    • 

  • Pyrrolidine
    • 

  • Amino acid or derivatives
    • 

  • Carboxylic acid ester
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Ether
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.73ALOGPS
logP2.79ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.77ChemAxon
pKa (Strongest Basic)10.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.19 m³·mol⁻¹ChemAxon
Polarizability42.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]