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Showing NP-Card for Cycloleucine (NP0083980)

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Record Information
Version2.0
Created at2022-04-29 04:51:30 UTC
Updated at2022-04-29 04:51:30 UTC
NP-MRD IDNP0083980
Secondary Accession NumbersNone
Natural Product Identification
Common NameCycloleucine
Description(2E)-Decenoyl-ACP, also known as cycloleucine or ACPC, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom (2E)-Decenoyl-ACP is a very strong basic compound (based on its pKa). Cycloleucine is found in Panax ginseng and Streptomyces hydrogenans. Cycloleucine was first documented in 1960 (PMID: 13880910). A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups (PMID: 13916973) (PMID: 13983935) (PMID: 15747318) (PMID: 22402366).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083980 (Cycloleucine)


  Mrv1652305052017402D          

  9  9  0  0  0  0            999 V2000
    0.0157    1.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   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  0  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  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    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
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
Download

3D MOL for NP0083980 (Cycloleucine)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
    0.5480   -1.3654    1.2375 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4960   -0.3423    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8231   -0.0638   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003   -0.7177    0.1044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746    0.8629   -1.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.9526    0.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3948    1.1620    0.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7932   -0.2953   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4874   -0.8189   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4629   -2.3022    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4574   -1.2934    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6416    1.6849   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5983    1.7983    0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808    0.7586    1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1533    1.6933    0.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1887    1.6556   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9502   -0.7775    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305   -0.3660   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778   -1.9170   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -0.3089   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
  7 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
  5 12  1  0
M  END
Download

3D SDF for NP0083980 (Cycloleucine)


  Mrv1652305052017402D          

  9  9  0  0  0  0            999 V2000
    0.0157    1.7274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   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  0  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  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9268    1.5559    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
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0083980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1(CCCC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)

> <INCHI_KEY>
NILQLFBWTXNUOE-UHFFFAOYSA-N

> <FORMULA>
C6H11NO2

> <MOLECULAR_WEIGHT>
129.157

> <EXACT_MASS>
129.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.226667802988839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-aminocyclopentane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.30

> <JCHEM_LOGP>
-1.8270617506905722

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.476824999493866

> <JCHEM_PKA_STRONGEST_BASIC>
9.82535845481508

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
32.456399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cycloleucine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0083980 (Cycloleucine)

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PDB for NP0083980 (Cycloleucine)
HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  N   UNK     0       0.029   3.224   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.614   4.689   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.597   2.904   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6    7                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0083980 (Cycloleucine)
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SMILES for NP0083980 (Cycloleucine)
NC1(CCCC1)C(O)=O
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INCHI for NP0083980 (Cycloleucine)
InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
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View in JSmol
Synonyms
ValueSource
1-Amino-1-carboxycyclopentaneChEBI
1-Amino-1-cyclopentanecarboxylic acidChEBI
1-Aminocyclopentane-1-carboxylic acidChEBI
ACPCChEBI
Cyclo-leucineChEBI
CycloleucinChEBI
CycloleucineChEBI
1-Aminocyclopentanecarboxylic acidKegg
1-Amino-1-cyclopentanecarboxylateGenerator
1-Aminocyclopentane-1-carboxylateGenerator
1-AminocyclopentanecarboxylateGenerator
1026, NSCHMDB
Aminocyclopentanecarboxylic acidHMDB
Acid, aminocyclopentanecarboxylicHMDB
1 Aminocyclopentanecarboxylic acidHMDB
Acid, 1-aminocyclopentanecarboxylicHMDB
Chemical FormulaC6H11NO2
Average Mass129.1570 Da
Monoisotopic Mass129.07898 Da
IUPAC Name1-aminocyclopentane-1-carboxylic acid
Traditional Namecycloleucine
CAS Registry NumberNot Available
SMILES
NC1(CCCC1)C(O)=O
InChI Identifier
InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
InChI KeyNILQLFBWTXNUOE-UHFFFAOYSA-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
Panax ginsengPlant
Streptomyces hydrogenansLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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
logP-2.3ALOGPS
logP-1.8ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)2.48ChemAxon
pKa (Strongest Basic)9.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.46 m³·mol⁻¹ChemAxon
Polarizability13.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062225  
DrugBank IDDB04620  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03969  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCycloleucine  
METLIN IDNot Available
PubChem Compound2901  
PDB IDNot Available
ChEBI ID40547  
Good Scents IDNot Available
References
General References
  1. CONNORS TA, ELSON LA, HADDOW A, ROSS WC: The pharmacology and tumour growth inhibitory activity of 1-aminocyclopentane-1-carboxylic acid and related compounds. Biochem Pharmacol. 1960 Oct;5:108-29. doi: 10.1016/0006-2952(60)90014-9. [PubMed:13880910  ] 
  2. STERLING WR, HENDERSON JF, MANDEL HG, SMITH PK: The metabolism of 1-aminocyclopentane-1-carboxylic acid in normal and neoplastic tissues. Biochem Pharmacol. 1962 Feb;11:135-45. doi: 10.1016/0006-2952(62)90100-4. [PubMed:13916973  ] 
  3. STERLING WR, HENDERSON JF: Studies of the mechanism of action 1-aminocyclopentane-1-carboxylic acid. Biochem Pharmacol. 1963 Apr;12:303-16. doi: 10.1016/0006-2952(63)90055-8. [PubMed:13983935  ] 
  4. Kowalczyk W, Prahl A, Dawidowska O, Derdowska I, Sobolewski D, Hartrodt B, Neubert K, Slaninova J, Lammek B: The influence of 1-aminocyclopentane-1-carboxylic acid at position 2 or 3 of AVP and its analogues on their pharmacological properties. J Pept Sci. 2005 Sep;11(9):584-8. doi: 10.1002/psc.656. [PubMed:15747318  ] 
  5. Carroll N, Hughes L, McEntee G, Parle-McDermott A: Investigation of the molecular response to folate metabolism inhibition. J Nutr Biochem. 2012 Nov;23(11):1531-6. doi: 10.1016/j.jnutbio.2011.10.006. Epub  2012 Mar 7. [PubMed:22402366  ]