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Showing NP-Card for Guanidine (NP0046667)

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Record Information
Version1.0
Created at2022-03-17 20:10:54 UTC
Updated at2022-03-17 20:10:54 UTC
NP-MRD IDNP0046667
Secondary Accession NumbersNone
Natural Product Identification
Common NameGuanidine
DescriptionGuanidine, also known as Gu or H2N-C(=nh)-NH2, 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. Guanidine is a drug which is used for the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of eaton-lambert. It is not indicated for treating myasthenia gravis. Guanidine is a very strong basic compound (based on its pKa). In humans, guanidine is involved in the metabolic disorder called the adenosine deaminase deficiency pathway. Outside of the human body, Guanidine has been detected, but not quantified in, several different foods, such as apples, corns, loquats, rices, and soy beans. This could make guanidine a potential biomarker for the consumption of these foods. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Guanidine is a potentially toxic compound. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Severe guanidine intoxication is characterized by nervous hyperirritability, fibrillary tremors and convulsive contractions of muscle, salivation, vomiting, diarrhea, hypoglycemia, and circulatory disturbances. Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). It was first documented in 1993 (PMID: 8512064). Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored (PMID: 7677341) (PMID: 8520461) (PMID: 8070089) (PMID: 11167434) (PMID: 7839077) (PMID: 10385678).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046667 (Guanidine)


  Mrv0541 02231214452D          

  4  3  0  0  0  0            999 V2000
    3.5219    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
M  END
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3D MOL for NP0046667 (Guanidine)

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3D SDF for NP0046667 (Guanidine)

  Mrv0541 02231214452D          

  4  3  0  0  0  0            999 V2000
    3.5219    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.7466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046667

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(N)=N

> <INCHI_IDENTIFIER>
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)

> <INCHI_KEY>
ZRALSGWEFCBTJO-UHFFFAOYSA-N

> <FORMULA>
CH5N3

> <MOLECULAR_WEIGHT>
59.0705

> <EXACT_MASS>
59.048347175

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
5.570297022100633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
guanidine

> <ALOGPS_LOGP>
-1.92

> <JCHEM_LOGP>
-1.236839015

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
12.547900248166645

> <JCHEM_POLAR_SURFACE_AREA>
75.89

> <JCHEM_REFRACTIVITY>
25.858800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046667 (Guanidine)
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PDB for NP0046667 (Guanidine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.574   0.916   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       3.907   0.916   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.241  -1.394   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.241   0.146   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4                                                            
CONECT    4    1    2    3                                                  
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END

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3D PDB for NP0046667 (Guanidine)
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SMILES for NP0046667 (Guanidine)
NC(N)=N
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INCHI for NP0046667 (Guanidine)
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
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View in JSmol
Synonyms
ValueSource
AminomethanamidineChEBI
GuChEBI
GuanidinChEBI
H2N-C(=nh)-NH2ChEBI
IminoureaChEBI
CarbamidineKegg
(4-Aminobutyl) guanidineHMDB
AminoformamidineHMDB
CarbamamidineHMDB
ImidoureaHMDB
Guanidine hydrochlorideHMDB
Guanidine monohydrateHMDB
Guanidine monohydrochlorideHMDB
Guanidine sulfateHMDB
Guanidium chlorideHMDB
Chloride, guanidiniumHMDB
Guanidine monohydroiodineHMDB
Guanidine sulfate (1:1)HMDB
Guanidine sulfate (2:1)HMDB
Guanidine sulfite (1:1)HMDB
GuanidiniumHMDB
Hydrochloride, guanidineHMDB
Monohydrobromide, guanidineHMDB
Monohydrochloride, guanidineHMDB
Phosphate, guanidineHMDB
Guanidine monohydrobromideHMDB
Guanidine phosphateHMDB
Monohydroiodine, guanidineHMDB
Nitrate, guanidineHMDB
Chloride, guanidiumHMDB
Guanidine nitrateHMDB
Guanidinium chlorideHMDB
Monohydrate, guanidineHMDB
Sulfate, guanidineHMDB
Chemical FormulaCH5N3
Average Mass59.0705 Da
Monoisotopic Mass59.04835 Da
IUPAC Nameguanidine
Traditional Nameguanidine
CAS Registry Number50-01-1
SMILES
NC(N)=N
InChI Identifier
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
InChI KeyZRALSGWEFCBTJO-UHFFFAOYSA-N
Experimental Spectra
Not Available
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
Eriobotrya japonicaFooDB
Gallus gallusFooDB
Glycine maxFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Oryza sativaFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Zea mays L.FooDB
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
    • 

  • Carboximidamide
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Imine
    • 

  • 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-1.9ALOGPS
logP-1.2ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)12.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.86 m³·mol⁻¹ChemAxon
Polarizability5.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001842  
DrugBank IDDB00536  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005416  
KNApSAcK IDNot Available
Chemspider ID3400  
KEGG Compound IDC17349  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanidine  
METLIN ID6342  
PubChem Compound3520  
PDB IDNot Available
ChEBI ID42820  
Good Scents IDNot Available
References
General References
  1. Atlas D: Molecular and physiological properties of clonidine-displacing substance. Ann N Y Acad Sci. 1995 Jul 12;763:314-24. [PubMed:7677341  ] 
  2. De Deyn PP, Marescau B, D'Hooge R, Possemiers I, Nagler J, Mahler C: Guanidino compound levels in brain regions of non-dialyzed uremic patients. Neurochem Int. 1995 Sep;27(3):227-37. [PubMed:8520461  ] 
  3. Taneda S, Monnier VM: ELISA of pentosidine, an advanced glycation end product, in biological specimens. Clin Chem. 1994 Sep;40(9):1766-73. [PubMed:8070089  ] 
  4. Bullough A, Karadia S, Watters M: Phaeochromocytoma: an unusual cause of hypertension in pregnancy. Anaesthesia. 2001 Jan;56(1):43-6. doi: 10.1046/j.1365-2044.2001.01726.x. [PubMed:11167434  ] 
  5. Mannik M, Person RE: Deep penetration of antibodies into the articular cartilage of patients with rheumatoid arthritis. Rheumatol Int. 1994;14(3):95-102. doi: 10.1007/BF00300809. [PubMed:7839077  ] 
  6. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. doi: 10.1124/mol.56.1.1. [PubMed:10385678  ] 
  7. Eropkin MIu, Smirnova TD, Eropkina EM, Mamaeva EG: [The study of the Ca2+ role in cytotoxic response of human cells in culture to the action of xenobiotics]. Tsitologiia. 2000;42(2):154-9. [PubMed:10752119  ] 
  8. Rufanova VA, Sorokin A: CrkII associates with BCAR3 in response to endothelin-1 in human glomerular mesangial cells. Exp Biol Med (Maywood). 2006 Jun;231(6):752-6. [PubMed:16740993  ] 
  9. Bjornsson S: Size-dependent separation of proteoglycans by electrophoresis in gels of pure agarose. Anal Biochem. 1993 May 1;210(2):292-8. doi: 10.1006/abio.1993.1198. [PubMed:8512064  ] 
  10. Sakamoto N, Toge T, Nishiyama M: Tumor-specific synergistic therapy of mitomycin C: modulation of bioreductive activation. Hiroshima J Med Sci. 1997 Jun;46(2):67-73. [PubMed:9232934  ] 
  11. Lorenzo P, Bayliss MT, Heinegard D: A novel cartilage protein (CILP) present in the mid-zone of human articular cartilage increases with age. J Biol Chem. 1998 Sep 4;273(36):23463-8. doi: 10.1074/jbc.273.36.23463. [PubMed:9722583  ] 
  12. Dabaghian RH, Barnard G, McConnell I, Clewley JP: An immunoassay for the pathological form of the prion protein based on denaturation and time resolved fluorometry. J Virol Methods. 2006 Mar;132(1-2):85-91. doi: 10.1016/j.jviromet.2005.09.002. Epub 2005 Oct 10. [PubMed:16219367  ] 
  13. Gothert M, Bruss M, Bonisch H, Molderings GJ: Presynaptic imidazoline receptors. New developments in characterization and classification. Ann N Y Acad Sci. 1999 Jun 21;881:171-84. doi: 10.1111/j.1749-6632.1999.tb09356.x. [PubMed:10415912  ] 
  14. Okumi M, Ueda T, Ichimaru N, Fujimoto N, Itoh K: [A case of composite pheochromocytoma-ganglioneuroblastoma in the adrenal gland with primary hyperparathyroidism]. Hinyokika Kiyo. 2003 May;49(5):269-72. [PubMed:12822455  ] 
  15. Leitersdorf E, Reshef A, Meiner V, Levitzki R, Schwartz SP, Dann EJ, Berkman N, Cali JJ, Klapholz L, Berginer VM: Frameshift and splice-junction mutations in the sterol 27-hydroxylase gene cause cerebrotendinous xanthomatosis in Jews or Moroccan origin. J Clin Invest. 1993 Jun;91(6):2488-96. doi: 10.1172/JCI116484. [PubMed:8514861  ]