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Showing NP-Card for Laburnine (NP0140062)

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Record Information
Version2.0
Created at2022-06-29 20:44:21 UTC
Updated at2022-06-29 20:44:21 UTC
NP-MRD IDNP0140062
Secondary Accession NumbersNone
Natural Product Identification
Common NameLaburnine
DescriptionLaburnine 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. Laburnine is found in Heliotropium indicum and Planchonella thyrsoidea. Laburnine was first documented in 2019 (PMID: 30894676). Based on a literature review very few articles have been published on Laburnine (PMID: 32459490).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140062 (Laburnine)


  Mrv1652306292222442D          

 10 11  0  0  1  0            999 V2000
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  2  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 N   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
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  6  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0140062 (Laburnine)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.1297    1.3329   -1.6308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737    0.4388   -0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796    0.3015    0.1963 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2415   -0.7018    1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1987   -1.1458    1.6188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9004   -1.0909    0.3739 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -0.4319    0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1573    0.7082   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561    0.4858   -1.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0764   -0.4057   -0.5835 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7371    2.1111   -1.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083    0.7752    0.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5175   -0.5588   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618    1.2649    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7044   -0.2286    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655   -1.5844    0.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -0.4751    2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925   -2.1794    1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -1.1704    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -0.0414    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0899    0.6875   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581    1.7070   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602   -0.0685   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666    1.4171   -1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -1.1472   -1.2503 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  1
  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 NP0140062 (Laburnine)


  Mrv1652306292222442D          

 10 11  0  0  1  0            999 V2000
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  2  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 N   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
    3.0937    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    1.8102    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  1  6  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140062

> <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-/m1/s1

> <INCHI_KEY>
LOFDEIYZIAVXHE-HTQZYQBOSA-N

> <FORMULA>
C8H15NO

> <MOLECULAR_WEIGHT>
141.214

> <EXACT_MASS>
141.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.335220545335822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.03138240566666668

> <ALOGPS_LOGS>
0.40

> <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

> <ALOGPS_SOLUBILITY>
3.54e+02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0140062 (Laburnine)

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PDB for NP0140062 (Laburnine)
HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.834  -1.246   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.775   2.235   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.744   3.379   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    8                                                  
CONECT    8    7    1                                                       
CONECT    9    4   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0140062 (Laburnine)
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SMILES for NP0140062 (Laburnine)
OC[C@H]1CCN2CCC[C@H]12
Download
INCHI for NP0140062 (Laburnine)
InChI=1S/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8-/m1/s1
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View in JSmol
Synonyms
ValueSource
(+)-LaburnineMeSH
Chemical FormulaC8H15NO
Average Mass141.2140 Da
Monoisotopic Mass141.11536 Da
IUPAC NameNot Available
Traditional NameNot Available
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-/m1/s1
InChI KeyLOFDEIYZIAVXHE-HTQZYQBOSA-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
Planchonella thyrsoideaLOTUS 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
    • 

  • Organopnictogen compound
    • 

  • 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID85067  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94259  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sarkale AM, Appayee C: Stereodivergent Synthesis of 1-Hydroxymethylpyrrolizidine Alkaloids. Org Lett. 2020 Jun 5;22(11):4355-4359. doi: 10.1021/acs.orglett.0c01375. Epub  2020 May 27. [PubMed:32459490  ] 
  2. Liang YF, Chung CC, Huang MW, Uang BJ: Formal syntheses of (-)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine. J Antibiot (Tokyo). 2019 Jun;72(6):397-406. doi: 10.1038/s41429-019-0169-9. Epub  2019 Mar 20. [PubMed:30894676  ]