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Showing NP-Card for (-)-trans-4-Hydroxy-N-methyl-L-proline (NP0074036)

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Record Information
Version2.0
Created at2022-04-28 19:14:02 UTC
Updated at2022-04-28 19:14:02 UTC
NP-MRD IDNP0074036
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-trans-4-Hydroxy-N-methyl-L-proline
Description(R)-4-hydroxy-1-methyl-L-proline, also known as N-methyl-trans-4-hydroxy-L-proline or NMH-pro, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (R)-4-hydroxy-1-methyl-L-proline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-trans-4-Hydroxy-N-methyl-L-proline is found in Acritopappus longifolius, Capsicum annuum , Chondria coerulescens, Cleidion spiciflorum (Burm. f.) Merr. , Copaifera langsdorffii, Croton megalobotrys, Ipomoea carnea, Melaleuca lanceolata, Tamarix aphylla , Tamarix jordanis, Tamarix meyeri, Tamarix nilotica, Tamarix parviflora, Tamarix ramossisima and Trichilia lepidota. (-)-trans-4-Hydroxy-N-methyl-L-proline was first documented in 2000 (PMID: 11199132). Based on a literature review a small amount of articles have been published on (R)-4-hydroxy-1-methyl-L-proline (PMID: 12903959) (PMID: 16425210) (PMID: 22071447) (PMID: 26427611).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)


  Mrv1652304282221142D          

 10 10  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    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  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  2  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  6  0  0  0
  1 10  1  0  0  0  0
M  END
Download

3D MOL for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -0.8699    1.9185    0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2773    0.8152   -0.3850 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2279   -0.1560   -0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.4153   -0.0478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7622   -1.4458    1.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524   -1.3160    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    0.1568    0.3129 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0396    0.3748   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0721    1.0431   -1.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205   -0.1755    0.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577    1.9186    0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4005    2.8516   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196    1.8366    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744    0.1859   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1052   -0.3039   -1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -2.2927   -0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.8042    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6320   -1.7395    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0663   -1.8783   -0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254    0.5482    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672   -0.1220   -0.4722 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  7  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  6
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  1
 10 21  1  0
M  END
Download

3D SDF for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)


  Mrv1652304282221142D          

 10 10  0  0  1  0            999 V2000
    0.5678    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0558    1.6913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    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  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  2  0  0  0  0
  6  8  1  0  0  0  0
  3  9  1  6  0  0  0
  1 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@H](O)C[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3/c1-7-3-4(8)2-5(7)6(9)10/h4-5,8H,2-3H2,1H3,(H,9,10)/t4-,5+/m1/s1

> <INCHI_KEY>
FMIPNAUMSPFTHK-UHNVWZDZSA-N

> <FORMULA>
C6H11NO3

> <MOLECULAR_WEIGHT>
145.158

> <EXACT_MASS>
145.073893218

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.225915212738665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-2.62

> <JCHEM_LOGP>
-3.591998916206618

> <ALOGPS_LOGS>
0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.847030393773316

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4843092046277553

> <JCHEM_PKA_STRONGEST_BASIC>
9.676438563800792

> <JCHEM_POLAR_SURFACE_AREA>
60.769999999999996

> <JCHEM_REFRACTIVITY>
34.6769

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)

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PDB for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)
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  N   UNK     0       1.060   2.080   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.971   3.157   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.795   0.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
CONECT    1    2    5   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    1                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)
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SMILES for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)
CN1C[C@H](O)C[C@H]1C(O)=O
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INCHI for NP0074036 ((-)-trans-4-Hydroxy-N-methyl-L-proline)
InChI=1S/C6H11NO3/c1-7-3-4(8)2-5(7)6(9)10/h4-5,8H,2-3H2,1H3,(H,9,10)/t4-,5+/m1/s1
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View in JSmol
Synonyms
ValueSource
(4R)-4-Hydroxy-1-methyl-L-prolineChEBI
(R)-4-Hydroxy-1-methylprolineChEBI
(R)-4-Hydroxy-N-methyl-L-prolineChEBI
(R)-4-Hydroxy-N-methylprolineChEBI
N-Methyl-trans-4-hydroxy-L-prolineChEBI
trans-4-Hydroxy-L-prolineMeSH
NMH-ProMeSH
Chemical FormulaC6H11NO3
Average Mass145.1580 Da
Monoisotopic Mass145.07389 Da
IUPAC Name(2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid
Traditional Name(2S,4R)-4-hydroxy-1-methylpyrrolidine-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN1C[C@H](O)C[C@H]1C(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c1-7-3-4(8)2-5(7)6(9)10/h4-5,8H,2-3H2,1H3,(H,9,10)/t4-,5+/m1/s1
InChI KeyFMIPNAUMSPFTHK-UHNVWZDZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acritopappus longifoliusLOTUS Database
Capsicum annuumPlant
Chondria coerulescensLOTUS Database
Cleidion spiciflorum (Burm. f.) Merr.Plant
Copaifera langsdorffiiLOTUS Database
Croton megalobotrysLOTUS Database
Ipomoea carneaLOTUS Database
Melaleuca lanceolataLOTUS Database
Tamarix aphyllaPlant
Tamarix jordanisPlant
Tamarix meyeriPlant
Tamarix niloticaPlant
Tamarix parvifloraPlant
Tamarix ramossisimaPlant
Trichilia lepidotaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentProline and derivatives  
Alternative Parents
Substituents
  • Proline or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Pyrrolidine carboxylic acid
    • 

  • Pyrrolidine carboxylic acid or derivatives
    • 

  • N-alkylpyrrolidine
    • 

  • Pyrrolidine
    • 

  • 1,2-aminoalcohol
    • 

  • Amino acid
    • 

  • Secondary alcohol
    • 

  • Tertiary amine
    • 

  • Tertiary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP-2.6ALOGPS
logP-3.6ChemAxon
logS0.89ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.68 m³·mol⁻¹ChemAxon
Polarizability14.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9943383  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11768700  
PDB IDNot Available
ChEBI ID134543  
Good Scents IDNot Available
References
General References
  1. Puripattanavong J, Weber S, Brecht V, Frahm AW: Phytochemical investigation of Aglaia andamanica. Planta Med. 2000 Dec;66(8):740-5. doi: 10.1055/s-2000-9901. [PubMed:11199132  ] 
  2. Haraguchi M, Gorniak SL, Ikeda K, Minami Y, Kato A, Watson AA, Nash RJ, Molyneux RJ, Asano N: Alkaloidal components in the poisonous plant, Ipomoea carnea (Convolvulaceae). J Agric Food Chem. 2003 Aug 13;51(17):4995-5000. doi: 10.1021/jf0341722. [PubMed:12903959  ] 
  3. Winkler T: Comments on 'Piperidone derivative from Dalbergia sympathetica'. Magn Reson Chem. 2006 May;44(5):571-2. doi: 10.1002/mrc.1783. [PubMed:16425210  ] 
  4. Moustapha B, Marina GA, Raul FO, Raquel CM, Mahinda M: Chemical constituents of the Mexican mistletoe (Psittacanthus calyculatus). Molecules. 2011 Nov 9;16(11):9397-403. doi: 10.3390/molecules16119397. [PubMed:22071447  ] 
  5. Puripattanavong J, Tungcharoen P, Chaniad P, Pianwanit S, Tewtrakul S: Anti-HIV-1 integrase effect of compounds from Aglaia andamanica leaves and molecular docking study with acute toxicity test in mice. Pharm Biol. 2016;54(4):654-9. doi: 10.3109/13880209.2015.1071413. Epub 2015 Oct 1. [PubMed:26427611  ]