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Showing NP-Card for (1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol (NP0286384)

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Record Information
Version2.0
Created at2022-09-09 14:56:00 UTC
Updated at2022-09-09 14:56:00 UTC
NP-MRD IDNP0286384
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol
DescriptionLindelofidine 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. (1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol is found in Heliotropium indicum and Heliotropium strigosum. Based on a literature review very few articles have been published on Lindelofidine.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)


  Mrv1652309092216562D          

 10 11  0  0  1  0            999 V2000
    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  2  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  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
  3 10  1  0  0  0  0
 10  6  1  6  0  0  0
M  END
Download

3D MOL for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    2.2171   -1.5413    0.7366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0937   -0.1821    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890    0.0177   -0.6661 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0154    1.5202   -0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4750    1.7881   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7439    0.7609    0.2666 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861    0.3645    0.4429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0017   -1.1443    0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5340   -1.4993    0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998   -0.3931   -0.4812 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1130   -1.7686    1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.2341    0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401    0.2928    1.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.4475   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    2.0953   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2836    1.7570   -1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9857    1.5844   -1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6391    2.8076   -0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    0.8263    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7718    0.5870   -0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2630   -1.3849    1.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5963   -1.7150   -0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -2.5137   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0290   -1.5349    1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250   -0.5113   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  3  1  0
 10  6  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  6
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  6
M  END
Download

3D SDF for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)


  Mrv1652309092216562D          

 10 11  0  0  1  0            999 V2000
    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  2  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  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
  3 10  1  0  0  0  0
 10  6  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0286384

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1CCN2CCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8+/m0/s1

> <INCHI_KEY>
LOFDEIYZIAVXHE-JGVFFNPUSA-N

> <FORMULA>
C8H15NO

> <MOLECULAR_WEIGHT>
141.214

> <EXACT_MASS>
141.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.12594457255797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,7aR)-hexahydro-1H-pyrrolizin-1-yl]methanol

> <JCHEM_LOGP>
0.03138240566666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.420323971873753

> <JCHEM_PKA_STRONGEST_BASIC>
10.4996142806747

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
41.0418

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7aR)-hexahydro-1H-pyrrolizin-1-ylmethanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)

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PDB for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       0.388  -3.507   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.834   0.294   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3    6                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)
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SMILES for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)
OC[C@@H]1CCN2CCC[C@H]12
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INCHI for NP0286384 ((1r,7ar)-hexahydro-1h-pyrrolizin-1-ylmethanol)
InChI=1S/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H15NO
Average Mass141.2140 Da
Monoisotopic Mass141.11536 Da
IUPAC Name[(1R,7aR)-hexahydro-1H-pyrrolizin-1-yl]methanol
Traditional Name(1R,7aR)-hexahydro-1H-pyrrolizin-1-ylmethanol
CAS Registry NumberNot Available
SMILES
OC[C@@H]1CCN2CCC[C@H]12
InChI Identifier
InChI=1S/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8+/m0/s1
InChI KeyLOFDEIYZIAVXHE-JGVFFNPUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Heliotropium indicumLOTUS Database
Heliotropium strigosumLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolizidines  
Sub ClassNot Available
Direct ParentPyrrolizidines  
Alternative Parents
Substituents
  • Pyrrolizidine
    • 

  • N-alkylpyrrolidine
    • 

  • 1,3-aminoalcohol
    • 

  • Pyrrolidine
    • 

  • Tertiary amine
    • 

  • Tertiary aliphatic amine
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Alcohol
    • 

  • Organic nitrogen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.031ChemAxon
pKa (Strongest Acidic)15.42ChemAxon
pKa (Strongest Basic)10.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.04 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9301481  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11126361  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]