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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015265

Secondary Accession Numbers

HMDB15265

Metabolite Identification

Common Name

Tiludronate

Description

Tiludronate is only found in individuals that have used or taken this drug. It is a bisphosphonate characterized by a (4-chlorophenylthio) group on the carbon atom of the basic P-C-P structure common to all bisphosphonates.The bisphosphonate group binds strongly to the bone mineral, hydroxyapatite. This explains the specific pharmacological action of these compounds on mineralized tissues, especially bone. In vitro studies indicate that tiludronate acts primarily on bone through a mechanism that involves inhibition of osteoclastic activity with a probable reduction in the enzymatic and transport processes that lead to resorption of the mineralized matrix. Bone resorption occurs following recruitment, activation, and polarization of osteoclasts. Tiludronate appears to inhibit osteoclasts by at least two mechanisms: disruption of the cytoskeletal ring structure, possibly by inhibition of protein-tyrosine-phosphatase, thus leading to detachment of osteoclasts from the bone surface and the inhibition of the osteoclastic proton pump.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1133
  Mrv0541 02231215162D          

 17 17  0  0  0  0            999 V2000
    2.3644   -2.8091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.4909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.7284    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4909    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    1.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -0.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  9  2  0  0  0  0
  3 11  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  2  0  0  0  0
  4 11  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015265

> <DATABASE_NAME>
hmdb

> <SMILES>
OP(O)(=O)C(SC1=CC=C(Cl)C=C1)P(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H9ClO6P2S/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14/h1-4,7H,(H2,9,10,11)(H2,12,13,14)

> <INCHI_KEY>
DKJJVAGXPKPDRL-UHFFFAOYSA-N

> <FORMULA>
C7H9ClO6P2S

> <MOLECULAR_WEIGHT>
318.608

> <EXACT_MASS>
317.928359441

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
25.370106515201513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(4-chlorophenyl)sulfanyl](phosphono)methyl}phosphonic acid

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
1.322081915

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.7849774430028384

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0278607867781062

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
65.1071

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiludronate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1133                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.414  -5.244   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       4.414   0.916   0.000  0.00  0.00           S+0
HETATM    3  P   UNK     0       5.747   3.226   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0       7.081   0.916   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0       5.747   4.766   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       7.287   3.226   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.415   0.146   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.851   2.250   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.207   3.226   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.311  -0.417   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.747   1.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -0.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -1.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -1.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -2.934   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -2.934   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.704   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   11   12                                                       
CONECT    3    5    6    9   11                                             
CONECT    4    7    8   10   11                                             
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    2    3    4                                                  
CONECT   12    2   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17    1   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0015265
HETATM    1  O1  UNL     1      -3.539  -0.163  -1.657  1.00  0.00           O  
HETATM    2  P1  UNL     1      -2.811   0.631  -0.565  1.00  0.00           P  
HETATM    3  O2  UNL     1      -3.922   0.925   0.707  1.00  0.00           O  
HETATM    4  O3  UNL     1      -2.292   2.053  -1.286  1.00  0.00           O  
HETATM    5  C1  UNL     1      -1.472  -0.412   0.035  1.00  0.00           C  
HETATM    6  S1  UNL     1      -0.372   0.561   1.072  1.00  0.00           S  
HETATM    7  C2  UNL     1       1.291   0.537   0.450  1.00  0.00           C  
HETATM    8  C3  UNL     1       2.175  -0.478   0.886  1.00  0.00           C  
HETATM    9  C4  UNL     1       3.473  -0.551   0.454  1.00  0.00           C  
HETATM   10  C5  UNL     1       3.954   0.402  -0.449  1.00  0.00           C  
HETATM   11 CL1  UNL     1       5.623   0.333  -1.029  1.00  0.00          CL  
HETATM   12  C6  UNL     1       3.104   1.405  -0.892  1.00  0.00           C  
HETATM   13  C7  UNL     1       1.797   1.445  -0.430  1.00  0.00           C  
HETATM   14  P2  UNL     1      -2.143  -1.841   0.926  1.00  0.00           P  
HETATM   15  O4  UNL     1      -3.507  -2.234   0.480  1.00  0.00           O  
HETATM   16  O5  UNL     1      -1.044  -3.140   0.837  1.00  0.00           O  
HETATM   17  O6  UNL     1      -2.263  -1.395   2.570  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.599   1.680   1.247  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.337   2.799  -0.606  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.887  -0.778  -0.869  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.788  -1.205   1.584  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.159  -1.322   0.789  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.512   2.143  -1.595  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.183   2.234  -0.815  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.331  -2.890   0.176  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.539  -0.740   2.729  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   18
CONECT    4   19
CONECT    5    6   14   20
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   11   12
CONECT   12   13   13   23
CONECT   13   24
CONECT   14   15   15   16   17
CONECT   16   25
CONECT   17   26
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tiludronic acid	Generator
Tiludronate disodium	HMDB
Tiludronic acid disodium salt	HMDB
(Chloro-4-phenyl)thiomethylene biphosphonate	HMDB
(Chloro-4-phenyl)thiomethylene bisphosphonate	HMDB
Skelid	HMDB
CL2SMBP	HMDB
(4-Chlorophenyl)thiomethylene bisphosphonic acid	HMDB
Tiludronate	KEGG

Chemical Formula

C₇H₉ClO₆P₂S

Average Molecular Weight

318.608

Monoisotopic Molecular Weight

317.928359441

IUPAC Name

{[(4-chlorophenyl)sulfanyl](phosphono)methyl}phosphonic acid

Traditional Name

tiludronate

CAS Registry Number

89987-06-4

SMILES

OP(O)(=O)C(SC1=CC=C(Cl)C=C1)P(O)(O)=O

InChI Identifier

InChI=1S/C7H9ClO6P2S/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14/h1-4,7H,(H2,9,10,11)(H2,12,13,14)

InChI Key

DKJJVAGXPKPDRL-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Bisphosphonates

Direct Parent

Bisphosphonates

Alternative Parents

Substituents

Bisphosphonate
Aryl thioether
Thiophenol ether
Chlorobenzene
Halobenzene
Alkylarylthioether
Benzenoid
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Organophosphonic acid
Sulfenyl compound
Thioether
Organopnictogen compound
Organosulfur compound
Organophosphorus compound
Organochloride
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:9598 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015265)
Membrane (HMDB: HMDB0015265)

Source

Exogenous

Exogenous (HMDB: HMDB0015265)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6.97 g/L	Not Available
LogP	-0.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.97 g/L	ALOGPS
logP	0.62	ALOGPS
logP	1.32	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.03	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.11 m³·mol⁻¹	ChemAxon
Polarizability	25.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	142.583	30932474
DeepCCS	[M-H]-	140.199	30932474
DeepCCS	[M-2H]-	173.671	30932474
DeepCCS	[M+Na]+	148.49	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	157.1	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	151.5	32859911
AllCCS	[M+Na-2H]-	151.8	32859911
AllCCS	[M+HCOO]-	152.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.54 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3543 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	519.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	660.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	346.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	56.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	111.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	289.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	283.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	781.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	723.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	72.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	611.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	304.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	704.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	357.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	324.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiludronate	OP(O)(=O)C(SC1=CC=C(Cl)C=C1)P(O)(O)=O	3957.1	Standard polar	33892256
Tiludronate	OP(O)(=O)C(SC1=CC=C(Cl)C=C1)P(O)(O)=O	2289.4	Standard non polar	33892256
Tiludronate	OP(O)(=O)C(SC1=CC=C(Cl)C=C1)P(O)(O)=O	2640.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tiludronate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2565.0	Semi standard non polar	33892256
Tiludronate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2415.4	Standard non polar	33892256
Tiludronate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	3598.6	Standard polar	33892256
Tiludronate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2549.9	Semi standard non polar	33892256
Tiludronate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2483.5	Standard non polar	33892256
Tiludronate,2TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	3139.0	Standard polar	33892256
Tiludronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C	2541.5	Semi standard non polar	33892256
Tiludronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C	2496.7	Standard non polar	33892256
Tiludronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C	3164.7	Standard polar	33892256
Tiludronate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2522.7	Semi standard non polar	33892256
Tiludronate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2532.2	Standard non polar	33892256
Tiludronate,3TMS,isomer #1	C[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2887.1	Standard polar	33892256
Tiludronate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2534.6	Semi standard non polar	33892256
Tiludronate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2547.6	Standard non polar	33892256
Tiludronate,4TMS,isomer #1	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2638.9	Standard polar	33892256
Tiludronate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2827.5	Semi standard non polar	33892256
Tiludronate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2622.9	Standard non polar	33892256
Tiludronate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	3730.1	Standard polar	33892256
Tiludronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	3039.2	Semi standard non polar	33892256
Tiludronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	2796.0	Standard non polar	33892256
Tiludronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O	3362.8	Standard polar	33892256
Tiludronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	3004.8	Semi standard non polar	33892256
Tiludronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	2830.1	Standard non polar	33892256
Tiludronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	3392.0	Standard polar	33892256
Tiludronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3181.3	Semi standard non polar	33892256
Tiludronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2976.3	Standard non polar	33892256
Tiludronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3171.7	Standard polar	33892256
Tiludronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3365.9	Semi standard non polar	33892256
Tiludronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3083.3	Standard non polar	33892256
Tiludronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(SC1=CC=C(Cl)C=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3025.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tiludronate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l6-9845000000-f6b7a670cc0b0a19c852	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiludronate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiludronate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 10V, Positive-QTOF	splash10-014i-0039000000-ab24506a08e68a6b0702	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 20V, Positive-QTOF	splash10-0079-1190000000-187e9be9bae033802f81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 40V, Positive-QTOF	splash10-001i-9320000000-3b1fcb1af6dc135e5934	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 10V, Negative-QTOF	splash10-000i-1093000000-d0499b987fed9300a204	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 20V, Negative-QTOF	splash10-014r-0092000000-02dee9f83fd33c231117	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 40V, Negative-QTOF	splash10-004i-9460000000-fb9cbdc13ede2f2f0469	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 10V, Positive-QTOF	splash10-014i-0009000000-16e04a189f8f1cd048f0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 20V, Positive-QTOF	splash10-000i-0292000000-7adac6b4c781032f795e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 40V, Positive-QTOF	splash10-0006-0900000000-65305b822786ab2f2f11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 10V, Negative-QTOF	splash10-014i-0009000000-1151161fb778a852bdd7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 20V, Negative-QTOF	splash10-0109-6952000000-4f81d1b1f35da54892c8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiludronate 40V, Negative-QTOF	splash10-002f-8911000000-00516dd0dcc6fd649077	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01133	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01133	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01133

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54905

KEGG Compound ID

C08141

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tiludronic acid

METLIN ID

Not Available

PubChem Compound

60937

PDB ID

Not Available

ChEBI ID

399299

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Murakami H, Takahashi N, Sasaki T, Udagawa N, Tanaka S, Nakamura I, Zhang D, Barbier A, Suda T: A possible mechanism of the specific action of bisphosphonates on osteoclasts: tiludronate preferentially affects polarized osteoclasts having ruffled borders. Bone. 1995 Aug;17(2):137-44. [PubMed:8554921 ]
Sansom LN, Necciari J, Thiercelin JF: Human pharmacokinetics of tiludronate. Bone. 1995 Nov;17(5 Suppl):479S-483S. [PubMed:8573422 ]
Rogers MJ: New insights into the molecular mechanisms of action of bisphosphonates. Curr Pharm Des. 2003;9(32):2643-58. [PubMed:14529538 ]

Enzymes

Enzyme Details

1. V-type proton ATPase catalytic subunit A

General function:: Involved in ATP binding
Specific function:: Catalytic subunit of the peripheral V1 complex of vacuolar ATPase. V-ATPase vacuolar ATPase is responsible for acidifying a variety of intracellular compartments in eukaryotic cells.
Gene Name:: ATP6V1A
Uniprot ID:: P38606
Molecular weight:: 68303.5

References

David P, Nguyen H, Barbier A, Baron R: The bisphosphonate tiludronate is a potent inhibitor of the osteoclast vacuolar H(+)-ATPase. J Bone Miner Res. 1996 Oct;11(10):1498-507. [PubMed:8889850 ]

Enzyme Details

2. Tyrosine-protein phosphatase non-receptor type 1

General function:: Involved in phosphatase activity
Specific function:: Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EIF2AK3/PERK. May play an important role in CKII- and p60c-src-induced signal transduction cascades. May regulate the EFNA5-EPHA3 signaling pathway which modulates cell reorganization and cell-cell repulsion.
Gene Name:: PTPN1
Uniprot ID:: P18031
Molecular weight:: 49966.44

References

Murakami H, Takahashi N, Tanaka S, Nakamura I, Udagawa N, Nakajo S, Nakaya K, Abe M, Yuda Y, Konno F, Barbier A, Suda T: Tiludronate inhibits protein tyrosine phosphatase activity in osteoclasts. Bone. 1997 May;20(5):399-404. [PubMed:9145236 ]

Showing metabocard for Tiludronate (HMDB0015265)

MOL for HMDB0015265 (Tiludronate)

3D MOL for HMDB0015265 (Tiludronate)

3D SDF for HMDB0015265 (Tiludronate)

3D-SDF for HMDB0015265 (Tiludronate)

PDB for HMDB0015265 (Tiludronate)

3D PDB for HMDB0015265 (Tiludronate)

SMILES for HMDB0015265 (Tiludronate)

INCHI for HMDB0015265 (Tiludronate)

Structure for HMDB0015265 (Tiludronate)

3D Structure for HMDB0015265 (Tiludronate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References