Np mrd loader

Showing NP-Card for Hygrine (NP0046979)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 20:32:38 UTC
Updated at2022-03-17 20:32:39 UTC
NP-MRD IDNP0046979
Secondary Accession NumbersNone
Natural Product Identification
Common NameHygrine
Description Hygrine is found in Atropa belladonna, Brugmansia candida, Convolvulus arvensis, Datura ferox, Datura inoxia, Datura quercifolia, Datura stramonium, Dendrobium chrysanthum, Dendrobium polyanthum, Duboisia myoporoides, Erythroxylum argentinum, Erythroxylum coca, Erythroxylum monogynum, Erythroxylum novogranatense, Erythroxylum zambesiacum, Hyoscyamus albus, Nierembergia hippomanica, Physalis peruviana, Picea breweriana, Sedum laconicum and Sedum urvillei. Hygrine was first documented in 1949 (PMID: 18224841).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046979 (Hygrine)


  Mrv1652309272007422D          

 10 10  0  0  0  0            999 V2000
10000.306410000.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0220 9999.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.735510000.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0220 9998.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938410001.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.920010000.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2526 9999.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5075 9998.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3325 9998.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5874 9999.7373    0.0000 C   0  0  2  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  2  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
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6  5  1  0  0  0  0
 10  1  1  1  0  0  0
M  END
Download

3D MOL for NP0046979 (Hygrine)

Download
3D SDF for NP0046979 (Hygrine)

  Mrv1652309272007422D          

 10 10  0  0  0  0            999 V2000
10000.306410000.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0220 9999.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.735510000.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0220 9998.9031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938410001.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.920010000.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2526 9999.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5075 9998.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3325 9998.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5874 9999.7373    0.0000 C   0  0  2  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  2  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
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6  5  1  0  0  0  0
 10  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC[C@@H]1CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1

> <INCHI_KEY>
ADKXZIOQKHHDNQ-MRVPVSSYSA-N

> <FORMULA>
C8H15NO

> <MOLECULAR_WEIGHT>
141.2108

> <EXACT_MASS>
141.115364107

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.3455702364747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
0.7003555696666667

> <ALOGPS_LOGS>
0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.542698879430624

> <JCHEM_PKA_STRONGEST_BASIC>
9.269051089694173

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
41.534400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-hygrine

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046979 (Hygrine)
Download
PDB for NP0046979 (Hygrine)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8667.2398666.927   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8668.5748666.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9068666.927   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8668.5748664.619   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8664.6858668.639   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0    8664.6518667.082   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8663.4058666.176   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.8818664.712   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.4218664.712   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.8968666.176   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6                                                            
CONECT    6    7   10    5                                                  
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6    1                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

Download
3D PDB for NP0046979 (Hygrine)
Download
SMILES for NP0046979 (Hygrine)
CN1CCC[C@@H]1CC(C)=O
Download
INCHI for NP0046979 (Hygrine)
InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(+)-HygrineChEBI
(+)-N-Methyl-2-acetonylpyrrolidineChEBI
(R)-(+)-HygrineChEBI
(R)-1-(1-Methyl-2-pyrrolidinyl)-2-propanoneChEBI
(R)-HygrineChEBI
1-[(2R)-1-Methylpyrrolidin-2-yl]acetoneChEBI
Hygrine, 2-(14)C-labeled, (+-)-isomerMeSH
1-[(2R)-1-Methyl-2-pyrrolidinyl]-2-propanonePhytoBank
D-(+)-HygrinePhytoBank
Chemical FormulaC8H15NO
Average Mass141.2108 Da
Monoisotopic Mass141.11536 Da
IUPAC Name1-[(2R)-1-methylpyrrolidin-2-yl]propan-2-one
Traditional Name(+)-hygrine
CAS Registry Number496-49-1
SMILES
CN1CCC[C@@H]1CC(C)=O
InChI Identifier
InChI=1S/C8H15NO/c1-7(10)6-8-4-3-5-9(8)2/h8H,3-6H2,1-2H3/t8-/m1/s1
InChI KeyADKXZIOQKHHDNQ-MRVPVSSYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Atropa belladonnaLOTUS Database
Brugmansia x candidaLOTUS Database
Convolvulus arvensisLOTUS Database
Datura feroxLOTUS Database
Datura inoxiaLOTUS Database
Datura quercifoliaLOTUS Database
Datura stramoniumLOTUS Database
Dendrobium chrysanthumLOTUS Database
Dendrobium polyanthumLOTUS Database
Duboisia myoporoidesLOTUS Database
Erythroxylum argentinumLOTUS Database
Erythroxylum cocaLOTUS Database
Erythroxylum monogynumLOTUS Database
Erythroxylum novogranatenseLOTUS Database
Erythroxylum zambesiacumLOTUS Database
Hyoscyamus albusLOTUS Database
Nierembergia hippomanicaLOTUS Database
Physalis peruvianaLOTUS Database
Picea brewerianaLOTUS Database
Punica granatumFooDB
Sedum laconicumLOTUS Database
Sedum urvilleiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives  
Alternative Parents
Substituents
  • Alkaloid or derivatives
    • 

  • Beta-aminoketone
    • 

  • N-alkylpyrrolidine
    • 

  • Pyrrolidine
    • 

  • Ketone
    • 

  • Tertiary amine
    • 

  • Tertiary aliphatic amine
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP0.71ALOGPS
logP0.7ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)18.54ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.53 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006790  
KNApSAcK IDC00002046  
Chemspider IDNot Available
KEGG Compound IDC06179  
BioCyc IDCPD-7995  
BiGG IDNot Available
Wikipedia Linkhygrine  
METLIN IDNot Available
PubChem Compound440933  
PDB IDNot Available
ChEBI ID46750  
Good Scents IDNot Available
References
General References
  1. Lee JH, Jeong BS, Ku JM, Jew SS, Park HG: Total synthesis of (+)-hygrine via asymmetric phase-transfer catalytic alkylation. J Org Chem. 2006 Aug 18;71(17):6690-2. doi: 10.1021/jo061108l. [PubMed:16901174  ] 
  2. ANET E, HUGHES GK, et al.: Syntheses of hygrine and cuscohygrine. Nature. 1949 Feb 19;163(4138):289. doi: 10.1038/163289a0. [PubMed:18224841  ] 
  3. McGaw BA, Woolley JC: The separate roles of hygrine enantiomers in the biosynthesis of tropane alkaloids [proceedings]. J Pharm Pharmacol. 1977 Dec;29 Suppl:16P. doi: 10.1111/j.2042-7158.1977.tb11484.x. [PubMed:22644  ] 
  4. Parr AJ: Alternative metabolic fates of hygrine in transformed root cultures of Nicandra physaloides. Plant Cell Rep. 1992 Jun;11(5-6):270-3. doi: 10.1007/BF00235080. [PubMed:24203138  ] 
  5. Rubio NC, Strano-Rossi S, Tabernero MJ, Gonzalez JL, Anzillotti L, Chiarotti M, Bermejo AM: Application of hygrine and cuscohygrine as possible markers to distinguish coca chewing from cocaine abuse on WDT and forensic cases. Forensic Sci Int. 2014 Oct;243:30-4. doi: 10.1016/j.forsciint.2014.02.024. Epub 2014 Mar 6. [PubMed:24656326  ]