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Showing NP-Card for Etidronic acid (NP0334584)

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Record Information
Version2.0
Created at2024-09-10 19:01:08 UTC
Updated at2024-09-10 19:01:09 UTC
NP-MRD IDNP0334584
Secondary Accession NumbersNone
Natural Product Identification
Common NameEtidronic acid
DescriptionEtidronic acid, also known as EHDP or etidronate, belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms. Etidronic acid is a drug which is used for the treatment of symptomatic paget's disease of bone and in the prevention and treatment of heterotopic ossification following total hip replacement or due to spinal cord injury. Etidronic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Etidronic acid is a potentially toxic compound. Etidronic acid was first documented in 1999 (PMID: 10385693). A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position (PMID: 11503828) (PMID: 17157266).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334584 (Etidronic acid)


  Mrv1572004031617522D          

 11 10  0  0  0  0            999 V2000
   12.6221   -5.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3367   -4.8401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0511   -5.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3367   -4.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9076   -4.8402    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -5.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9076   -4.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2096   -5.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0345   -5.9671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0512   -4.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -4.4277    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
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  1  8  1  0  0  0  0
  9  1  1  0  0  0  0
  2 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
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3D MOL for NP0334584 (Etidronic acid)

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3D SDF for NP0334584 (Etidronic acid)

  Mrv1572004031617522D          

 11 10  0  0  0  0            999 V2000
   12.6221   -5.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3367   -4.8401    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0511   -5.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3367   -4.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9076   -4.8402    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -5.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9076   -4.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2096   -5.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0345   -5.9671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0512   -4.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1931   -4.4277    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
  2  4  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  1  8  1  0  0  0  0
  9  1  1  0  0  0  0
  2 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(P(O)(O)=O)P(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)

> <INCHI_KEY>
DBVJJBKOTRCVKF-UHFFFAOYSA-N

> <FORMULA>
C2H8O7P2

> <MOLECULAR_WEIGHT>
206.027

> <EXACT_MASS>
205.974526594

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.965806979078927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1-hydroxy-1-phosphonoethyl)phosphonic acid

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-2.2774973313333327

> <ALOGPS_LOGS>
-1.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.4590138001772868

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6962425108147441

> <JCHEM_PKA_STRONGEST_BASIC>
-5.083644255238625

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
34.511

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
etidronic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334584 (Etidronic acid)
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PDB for NP0334584 (Etidronic acid)
HEADER    PROTEIN                                 03-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-16         0                                  
HETATM    1  C   UNK     0      23.561  -9.805   0.000  0.00  0.00           C+0
HETATM    2  P   UNK     0      24.895  -9.035   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      26.229  -9.805   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.895  -7.495   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      22.228  -9.035   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0      20.894  -9.805   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      22.228  -7.495   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.791 -11.139   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      24.331 -11.139   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      26.229  -8.265   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      20.894  -8.265   0.000  0.00  0.00           O+0
CONECT    1    2    5    8    9                                             
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    5                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0334584 (Etidronic acid)
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SMILES for NP0334584 (Etidronic acid)
CC(O)(P(O)(O)=O)P(O)(O)=O
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INCHI for NP0334584 (Etidronic acid)
InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)
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View in JSmol
Synonyms
ValueSource
(1-Hydroxyethylene)diphosphonic acidChEBI
(1-Hydroxyethylidene)bis(phosphonic acid)ChEBI
(1-Hydroxyethylidene)bisphosphonic acidChEBI
(1-Hydroxyethylidene)diphosphonic acidChEBI
(Hydroxyethylidene)diphosphonic acidChEBI
1,1,1-Ethanetriol diphosphonateChEBI
1-Hydroxy-1,1-diphosphonoethaneChEBI
1-Hydroxyethane-1,1-bisphosphonic acidChEBI
1-Hydroxyethane-1,1-diphosphonateChEBI
1-Hydroxyethane-1,1-diphosphonic acidChEBI
1-Hydroxyethanediphosphonic acidChEBI
1-Hydroxyethylidene-1,1-bisphosphonateChEBI
1-Hydroxyethylidene-1,1-diphosphonic acidChEBI
Acetodiphosphonic acidChEBI
Acide etidroniqueChEBI
Acido etidronicoChEBI
Acidum etidronicumChEBI
EHDPChEBI
Ethane-1-hydroxy-1,1-bisphosphonic acidChEBI
Ethane-1-hydroxy-1,1-diphosphonateChEBI
Ethane-1-hydroxy-1,1-diphosphonic acidChEBI
EtidronateChEBI
EtidronsaeureChEBI
HEDPChEBI
Hydroxyethanediphosphonic acidChEBI
Oxyethylidenediphosphonic acidChEBI
Ethane-1-hydroxy-1,1-bisphosphonateKegg
(1-Hydroxyethylene)diphosphonateGenerator
(1-Hydroxyethylidene)bis(phosphonate)Generator
(1-Hydroxyethylidene)bisphosphonateGenerator
(1-Hydroxyethylidene)diphosphonateGenerator
(Hydroxyethylidene)diphosphonateGenerator
1,1,1-Ethanetriol diphosphonic acidGenerator
1-Hydroxyethane-1,1-bisphosphonateGenerator
1-HydroxyethanediphosphonateGenerator
1-Hydroxyethylidene-1,1-bisphosphonic acidGenerator
1-Hydroxyethylidene-1,1-diphosphonateGenerator
AcetodiphosphonateGenerator
HydroxyethanediphosphonateGenerator
OxyethylidenediphosphonateGenerator
Etidronate disodiumHMDB
1 Hydroxyethane 1,1 diphosphonateHMDB
1,1 HydroxyethylenediphosphonateHMDB
Dicalcium ehdpHMDB
Dicalcium etidronateHMDB
Diphosphonic acid, hydroxyethylideneHMDB
Etidronate, sodiumHMDB
Hydroxyethylidene diphosphonic acidHMDB
Sodium etidronateHMDB
XidiphonHMDB
(1-Hydroxyethylene)diphosphonic acid, tetrapotassium saltHMDB
DidronelHMDB
Disodium 1-hydroxyethylene diphosphonateHMDB
EthanehydroxydiphosphonateHMDB
EthanehydroxyphosphateHMDB
Salt etidronate, tetrapotassiumHMDB
1 Hydroxyethylidene 1,1 bisphosphonateHMDB
1,1-HydroxyethylenediphosphonateHMDB
Diphosphonate, disodium 1-hydroxyethyleneHMDB
Disodium 1 hydroxyethylene diphosphonateHMDB
EHDP, dicalciumHMDB
Etidronate, disodiumHMDB
Etidronate, tetrapotassium saltHMDB
Phosphonic acid, (1-hydroxyethylidene)bis-, disodium saltHMDB
Tetrapotassium salt etidronateHMDB
XidifonHMDB
XydiphoneHMDB
1-Hydroxyethylene diphosphonate, disodiumHMDB
Disodium etidronateHMDB
Etidronate, dicalciumHMDB
HEDSPAHMDB
Chemical FormulaC2H8O7P2
Average Mass206.0270 Da
Monoisotopic Mass205.97453 Da
IUPAC Name(1-hydroxy-1-phosphonoethyl)phosphonic acid
Traditional Nameetidronic acid
CAS Registry NumberNot Available
SMILES
CC(O)(P(O)(O)=O)P(O)(O)=O
InChI Identifier
InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)
InChI KeyDBVJJBKOTRCVKF-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 bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic phosphonic acids and derivatives  
Sub ClassBisphosphonates  
Direct ParentBisphosphonates  
Alternative Parents
Substituents
  • Bisphosphonate
    • 

  • Organophosphonic acid
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organophosphorus compound
    • 

  • Organooxygen compound
    • 

  • 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-0.77ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.7ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.51 m³·mol⁻¹ChemAxon
Polarizability13.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0015210  
DrugBank IDDB01077  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001018  
KNApSAcK IDNot Available
Chemspider ID3189  
KEGG Compound IDC07736  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtidronic_acid  
METLIN IDNot Available
PubChem Compound3305  
PDB ID911  
ChEBI ID4907  
Good Scents IDNot Available
References
General References
  1. Benford HL, Frith JC, Auriola S, Monkkonen J, Rogers MJ: Farnesol and geranylgeraniol prevent activation of caspases by aminobisphosphonates: biochemical evidence for two distinct pharmacological classes of bisphosphonate drugs. Mol Pharmacol. 1999 Jul;56(1):131-40. doi: 10.1124/mol.56.1.131. [PubMed:10385693  ] 
  2. Authors unspecified: Etidronic acid and steroid therapy: new indication. No proven impact on fractures. Prescrire Int. 1999 Aug;8(42):111-2. [PubMed:11503828  ] 
  3. Moreau MF, Guillet C, Massin P, Chevalier S, Gascan H, Basle MF, Chappard D: Comparative effects of five bisphosphonates on apoptosis of macrophage cells in vitro. Biochem Pharmacol. 2007 Mar 1;73(5):718-23. doi: 10.1016/j.bcp.2006.09.031. Epub  2006 Nov 3. [PubMed:17157266  ]