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Showing NP-Card for 2-Aminoethylphosphonic acid (NP0002693)

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Record Information
Version1.0
Created at2020-11-23 19:38:06 UTC
Updated at2021-08-12 19:51:52 UTC
NP-MRD IDNP0002693
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Aminoethylphosphonic acid
Provided ByBMRBBMRB logo
DescriptionCiliatine belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. Ciliatine exists in all living organisms, ranging from bacteria to humans. Ciliatine 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. 2-Aminoethylphosphonic acid is found in Euphausia superba, Homo sapiens, Mus musculus, Streptomyces regensis and Tetrahymena pyriformis. It was first documented in 1967 (PMID: 4385371). Based on a literature review a significant number of articles have been published on Ciliatine (PMID: 17984079) (PMID: 4963810) (PMID: 6056747) (PMID: 21108683).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002693 (2-Aminoethylphosphonic acid)


     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.8732    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268    0.0000    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.1268    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258   -2.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    2.2500    0.0000 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  2  0
  4  6  1  6
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  1
  2 11  1  0
  3 12  1  1
  3 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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3D MOL for NP0002693 (2-Aminoethylphosphonic acid)

NP0002693
     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    1.6921   -0.0240    0.9357 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569   -0.8943    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313   -0.2522   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    0.5030   -0.0396 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.5221    0.5386   -1.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -0.4613    1.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790    2.0626    0.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218    0.0191    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543    0.9439    0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007   -1.7351    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224   -1.3537   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780   -1.0861   -1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    0.4612   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783   -1.3686    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    2.6469   -0.1691 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  2  0
  4  6  1  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0002693 (2-Aminoethylphosphonic acid)


     RDKit          2D

 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.8732    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268    0.0000    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.1268    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6268    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232    1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3732    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258   -2.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258    2.2500    0.0000 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  2  0
  4  6  1  6
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  1
  2 11  1  0
  3 12  1  1
  3 13  1  0
  6 14  1  0
  7 15  1  0
M  END
> <DATABASE_ID>
NP0002693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H8NO3P/c3-1-2-7(4,5)6/h1-3H2,(H2,4,5,6)

> <INCHI_KEY>
QQVDJLLNRSOCEL-UHFFFAOYSA-N

> <FORMULA>
C2H8NO3P

> <MOLECULAR_WEIGHT>
125.0636

> <EXACT_MASS>
125.024179639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.24056079980689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethyl)phosphonic acid

> <ALOGPS_LOGP>
-1.55

> <JCHEM_LOGP>
-3.171460567993441

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.074020584720293

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.529000017826442

> <JCHEM_PKA_STRONGEST_BASIC>
10.428706348273401

> <JCHEM_POLAR_SURFACE_AREA>
83.55

> <JCHEM_REFRACTIVITY>
25.2516

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ciliatine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002693 (2-Aminoethylphosphonic acid)

NP0002693
     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    1.6921   -0.0240    0.9357 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569   -0.8943    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313   -0.2522   -0.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346    0.5030   -0.0396 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.5221    0.5386   -1.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -0.4613    1.2645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0790    2.0626    0.4900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218    0.0191    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543    0.9439    0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6007   -1.7351    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224   -1.3537   -0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780   -1.0861   -1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    0.4612   -1.5940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9783   -1.3686    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    2.6469   -0.1691 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  2  0
  4  6  1  0
  4  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  6 14  1  0
  7 15  1  0
M  END
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PDB for NP0002693 (2-Aminoethylphosphonic acid)

HEADER    PROTEIN                                 12-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-17         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  P   UNK     0       3.850  -1.334   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0       5.390  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.850   0.206   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.850  -2.874   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0002693 (2-Aminoethylphosphonic acid)

COMPND    NP0002693
HETATM    1  N1  UNL     1       1.692  -0.024   0.936  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.057  -0.894   0.013  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.031  -0.252  -0.873  1.00  0.00           C  
HETATM    4  P1  UNL     1      -1.335   0.503  -0.040  1.00  0.00           P  
HETATM    5  O1  UNL     1      -2.522   0.539  -1.008  1.00  0.00           O  
HETATM    6  O2  UNL     1      -1.814  -0.461   1.264  1.00  0.00           O  
HETATM    7  O3  UNL     1      -1.079   2.063   0.490  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.722   0.019   0.756  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.354   0.944   0.946  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.601  -1.735   0.575  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.822  -1.354  -0.665  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.378  -1.086  -1.519  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.480   0.461  -1.594  1.00  0.00           H  
HETATM   14  H7  UNL     1      -1.978  -1.369   0.887  1.00  0.00           H  
HETATM   15  H8  UNL     1      -0.653   2.647  -0.169  1.00  0.00           H  
CONECT    1    2    8    9
CONECT    2    3   10   11
CONECT    3    4   12   13
CONECT    4    5    5    6    7
CONECT    6   14
CONECT    7   15
END
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SMILES for NP0002693 (2-Aminoethylphosphonic acid)

NCCP(O)(O)=O
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INCHI for NP0002693 (2-Aminoethylphosphonic acid)

InChI=1S/C2H8NO3P/c3-1-2-7(4,5)6/h1-3H2,(H2,4,5,6)
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View in JSmol
Synonyms
ValueSource
(2-Aminoethane)phosphonic acidChEBI
(2-Aminoethyl)phosphonateChEBI
2-AminoethylphosphonateChEBI
Aminoethylphosphonic acidChEBI
beta-Aminoethylphosphonic acidChEBI
PhosphonoethylamineChEBI
(2-Aminoethane)phosphonateGenerator
(2-Aminoethyl)phosphonic acidGenerator
2-Aminoethylphosphonic acidGenerator
AminoethylphosphonateGenerator
b-AminoethylphosphonateGenerator
b-Aminoethylphosphonic acidGenerator
beta-AminoethylphosphonateGenerator
Β-aminoethylphosphonateGenerator
Β-aminoethylphosphonic acidGenerator
2 Aminoethylphosphonic acidMeSH, HMDB
Acid, 2-aminoethylphosphonicMeSH, HMDB
Acid, aminoethylphosphonicMeSH, HMDB
CiliatineChEBI
Chemical FormulaC2H8NO3P
Average Mass125.0636 Da
Monoisotopic Mass125.02418 Da
IUPAC Name(2-aminoethyl)phosphonic acid
Traditional Nameciliatine
CAS Registry NumberNot Available
SMILES
NCCP(O)(O)=O
InChI Identifier
InChI=1S/C2H8NO3P/c3-1-2-7(4,5)6/h1-3H2,(H2,4,5,6)
InChI KeyQQVDJLLNRSOCEL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Euphausia superbaLOTUS Database
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mitragyna speciosa Korth.KNApSAcK Database
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Streptomyces regensisLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tetrahymena pyriformisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic phosphonic acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic 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-1.6ALOGPS
logP-3.2ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)10.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.25 m³·mol⁻¹ChemAxon
Polarizability10.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011747
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028420
KNApSAcK IDC00025209
Chemspider ID332
KEGG Compound IDC03557
BioCyc IDCPD-1106
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound339
PDB IDP7I
ChEBI ID15573
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Trebst A, Geike F: [On the biosynthesis of phosphonamino acids. The distribution of radioactivity in aminoethylphosphonic acid following incorporation of position-labelled glucose by Tetrahymena]. Z Naturforsch B. 1967 Sep;22(9):989-91. [PubMed:4385371 ]
  3. Rosenberg H, La Nauze JM: The metabolism of phosphonates by microorganisms. The transport of aminoethylphosphonic acid in Bacillus cereus. Biochim Biophys Acta. 1967 Jun 13;141(1):79-90. doi: 10.1016/0304-4165(67)90247-4. [PubMed:4963810 ]
  4. Carayon-Gentil A, Savignac P, Thuong NT, Chabrier P: [New method of preparation of beta-aminoethylphosphonic acid]. Bull Soc Chim Biol (Paris). 1967 Jul 27;49(7):873-7. [PubMed:6056747 ]
  5. Moon YH, Ok JU, Lee SJ, Ha JK, Lee SS: Comparative study on the rumen microbial populations, hydrolytic enzyme activities and dry matter degradability between different species of ruminant. Anim Sci J. 2010 Dec;81(6):642-7. doi: 10.1111/j.1740-0929.2010.00782.x. Epub 2010 Oct 7. [PubMed:21108683 ]