Np mrd loader

Showing NP-Card for beta-Guanidinopropionic acid (NP0339222)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 20:30:09 UTC
Updated at2024-09-11 20:30:09 UTC
NP-MRD IDNP0339222
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-Guanidinopropionic acid
DescriptionBeta-Guanidinopropionic acid, also known as N-[amino(imino)methyl]-b-alanine or b-guanidinopropionate, belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. Beta-Guanidinopropionic acid is a very strong basic compound (based on its pKa). beta-Guanidinopropionic acid was first documented in 1995 (PMID: 7491263). Beta-Guanidinopropionic acid is analog of creatine and is reported to decrease phosphocreatine and ATP content in animal tissues in vivo (PMID: 19358571) (PMID: 23326362) (PMID: 7900770).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339222 (beta-Guanidinopropionic acid)


  Mrv1652303102016512D          

  9  8  0  0  0  0            999 V2000
    3.5942  -12.8794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -12.8794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -12.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -11.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8811  -12.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666  -11.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  2  0  0  0  0
M  END
Download

3D MOL for NP0339222 (beta-Guanidinopropionic acid)

Download
3D SDF for NP0339222 (beta-Guanidinopropionic acid)

  Mrv1652303102016512D          

  9  8  0  0  0  0            999 V2000
    3.5942  -12.8794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0231  -12.8794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521  -12.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666  -12.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086  -11.6419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8811  -12.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666  -11.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=N)NCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)

> <INCHI_KEY>
KMXXSJLYVJEBHI-UHFFFAOYSA-N

> <FORMULA>
C4H9N3O2

> <MOLECULAR_WEIGHT>
131.1332

> <EXACT_MASS>
131.069476547

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.493162763286698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carbamimidamidopropanoic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-2.889204979082051

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9836477892739883

> <JCHEM_PKA_STRONGEST_BASIC>
12.617530902860116

> <JCHEM_POLAR_SURFACE_AREA>
99.19999999999999

> <JCHEM_REFRACTIVITY>
41.4174

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-guanidinopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339222 (beta-Guanidinopropionic acid)
Download
PDB for NP0339222 (beta-Guanidinopropionic acid)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  N   UNK     0       6.709 -24.042   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.043 -23.272   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       9.376 -24.042   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      10.710 -23.272   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.044 -24.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.378 -23.272   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.043 -21.732   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      14.711 -24.042   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      13.378 -21.732   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    8    9                                                  
CONECT    7    2                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

Download
3D PDB for NP0339222 (beta-Guanidinopropionic acid)
Download
SMILES for NP0339222 (beta-Guanidinopropionic acid)
NC(=N)NCCC(O)=O
Download
INCHI for NP0339222 (beta-Guanidinopropionic acid)
InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)
Download
View in JSmol
Synonyms
ValueSource
3-GuanidinopropanoateChEBI
beta-GPAChEBI
N-[Amino(imino)methyl]-beta-alanineChEBI
Guanidinopropionic acidKegg
3-Guanidinopropanoic acidGenerator
b-GPAGenerator
Β-gpaGenerator
N-[Amino(imino)methyl]-b-alanineGenerator
N-[Amino(imino)methyl]-β-alanineGenerator
GuanidinopropionateGenerator
b-GuanidinopropionateGenerator
b-Guanidinopropionic acidGenerator
beta-GuanidinopropionateGenerator
Β-guanidinopropionateGenerator
Β-guanidinopropionic acidGenerator
3-Guanidinopropionic acidHMDB
beta-GuanadinopropionateHMDB
beta-Guanidinopropionic acid.HMDB
beta-Guanidine propionic acidHMDB
Guanidine propionateHMDB
beta-Guanidinopropionic acidChEBI
Amidino beta-alanineMeSH
Chemical FormulaC4H9N3O2
Average Mass131.1332 Da
Monoisotopic Mass131.06948 Da
IUPAC Name3-carbamimidamidopropanoic acid
Traditional Name3-guanidinopropanoic acid
CAS Registry NumberNot Available
SMILES
NC(=N)NCCC(O)=O
InChI Identifier
InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7)
InChI KeyKMXXSJLYVJEBHI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassGuanidines  
Direct ParentGuanidines  
Alternative Parents
Substituents
  • Guanidine
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Carboximidamide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-1.7ALOGPS
logP-2.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)12.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.2 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity41.42 m³·mol⁻¹ChemAxon
Polarizability12.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013222  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029341  
KNApSAcK IDNot Available
Chemspider ID61020  
KEGG Compound IDC03065  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanidinopropionic_acid  
METLIN IDNot Available
PubChem Compound67701  
PDB IDNot Available
ChEBI ID15968  
Good Scents IDNot Available
References
General References
  1. Metzner L, Dorn M, Markwardt F, Brandsch M: The orally active antihyperglycemic drug beta-guanidinopropionic acid is transported by the human proton-coupled amino acid transporter hPAT1. Mol Pharm. 2009 May-Jun;6(3):1006-11. doi: 10.1021/mp9000684. [PubMed:19358571  ] 
  2. Oudman I, Clark JF, Brewster LM: The effect of the creatine analogue beta-guanidinopropionic acid on energy metabolism: a systematic review. PLoS One. 2013;8(1):e52879. doi: 10.1371/journal.pone.0052879. Epub 2013 Jan 9. [PubMed:23326362  ] 
  3. Ren JM, Ohira Y, Holloszy JO, Hamalainen N, Traub I, Pette D: Effects of beta-guanidinopropionic acid-feeding on the patterns of myosin isoforms in rat fast-twitch muscle. Pflugers Arch. 1995 Jul;430(3):389-93. doi: 10.1007/BF00373914. [PubMed:7491263  ] 
  4. Boehm EA, Clark JF, Radda GK: Metabolite utilization and compartmentation in porcine carotid artery: a study using beta-guanidinopropionic acid. Am J Physiol. 1995 Mar;268(3 Pt 1):C628-35. doi: 10.1152/ajpcell.1995.268.3.C628. [PubMed:7900770  ]