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enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014543

Secondary Accession Numbers

HMDB14543

Metabolite Identification

Common Name

Zoledronate

Description

Zoledronate (zoledronic acid, marketed by Novartis under the trade names Zometa and Reclast) is a bisphosphonate. Zometa is used to prevent skeletal fractures in patients with cancers such as multiple myeloma and prostate cancer. It can also be used to treat hypercalcemia of malignancy and can be helpful for treating pain from bone metastases. An annual dose of Zoledronate may also prevent recurring fractures in patients with a previous hip fracture. Zoledronate is a single 5 mg infusion for the treatment of Paget's disease of bone. In 2007, the FDA also approved Reclast for the treatment of postmenopausal osteoporosis.

Structure

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

68740
  Mrv0541 02231214392D          

 16 16  0  0  0  0            999 V2000
    2.5741   -0.9212    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010   -1.2232    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.8760    0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -1.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155   -0.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8596   -1.3337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1615   -0.2067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4189   -1.9984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308   -1.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030    0.7288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4155    1.9984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0030   -0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3355    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    1.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5905    1.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  9  2  0  0  0  0
  1 12  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  8  2  0  0  0  0
  2 12  1  0  0  0  0
  3 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014543

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)

> <INCHI_KEY>
XRASPMIURGNCCH-UHFFFAOYSA-N

> <FORMULA>
C5H10N2O7P2

> <MOLECULAR_WEIGHT>
272.0896

> <EXACT_MASS>
271.996323708

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
20.097260908269067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acid

> <ALOGPS_LOGP>
-0.93

> <JCHEM_LOGP>
-3.851108564002269

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.4203844443343967

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6570370453814713

> <JCHEM_PKA_STRONGEST_BASIC>
6.674963447469139

> <JCHEM_POLAR_SURFACE_AREA>
153.11

> <JCHEM_REFRACTIVITY>
52.157700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zoledronate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 68740                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0       4.805  -1.720   0.000  0.00  0.00           P+0
HETATM    2  P   UNK     0       6.909  -2.283   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       5.369   0.384   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.679  -3.617   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.242  -1.513   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.471  -2.490   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.035  -0.386   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.382  -3.730   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.537  -3.236   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       7.472   1.360   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       8.242   3.730   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.139  -0.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.472  -0.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.226   2.266   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.718   2.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.702   3.730   0.000  0.00  0.00           C+0
CONECT    1    6    7    9   12                                             
CONECT    2    4    5    8   12                                             
CONECT    3   12                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    1                                                            
CONECT   10   13   14   15                                                  
CONECT   11   15   16                                                       
CONECT   12    1    2    3   13                                             
CONECT   13   10   12                                                       
CONECT   14   10   16                                                       
CONECT   15   10   11                                                       
CONECT   16   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0014543
HETATM    1  O1  UNL     1      -2.366  -1.918  -0.315  1.00  0.00           O  
HETATM    2  P1  UNL     1      -1.237  -1.036  -0.853  1.00  0.00           P  
HETATM    3  O2  UNL     1      -0.023  -2.076  -1.425  1.00  0.00           O  
HETATM    4  O3  UNL     1      -1.822  -0.048  -2.074  1.00  0.00           O  
HETATM    5  C1  UNL     1      -0.615  -0.088   0.564  1.00  0.00           C  
HETATM    6  O4  UNL     1      -0.235  -1.027   1.509  1.00  0.00           O  
HETATM    7  C2  UNL     1       0.488   0.849   0.176  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.636   0.223  -0.385  1.00  0.00           N  
HETATM    9  C3  UNL     1       2.721  -0.235   0.248  1.00  0.00           C  
HETATM   10  C4  UNL     1       3.565  -0.758  -0.699  1.00  0.00           C  
HETATM   11  N2  UNL     1       2.971  -0.605  -1.882  1.00  0.00           N  
HETATM   12  C5  UNL     1       1.784  -0.003  -1.699  1.00  0.00           C  
HETATM   13  P2  UNL     1      -2.005   0.943   1.162  1.00  0.00           P  
HETATM   14  O5  UNL     1      -3.331   0.290   0.846  1.00  0.00           O  
HETATM   15  O6  UNL     1      -1.891   1.224   2.811  1.00  0.00           O  
HETATM   16  O7  UNL     1      -1.981   2.421   0.315  1.00  0.00           O  
HETATM   17  H1  UNL     1      -0.469  -2.888  -1.775  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.812   0.040  -1.926  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.193  -0.673   2.425  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.066   1.571  -0.553  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.817   1.465   1.039  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.939  -0.216   1.323  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.533  -1.204  -0.461  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.072   0.251  -2.507  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.925   0.337   3.268  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.687   3.161   0.868  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   17
CONECT    4   18
CONECT    5    6    7   13
CONECT    6   19
CONECT    7    8   20   21
CONECT    8    9   12
CONECT    9   10   10   22
CONECT   10   11   23
CONECT   11   12   12
CONECT   12   24
CONECT   13   14   14   15   16
CONECT   15   25
CONECT   16   26
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acid	ChEBI
(1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonic acid	ChEBI
Reclast	ChEBI
ZOL	ChEBI
Zometa	Kegg
(1-Hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonate	Generator
(1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonate	Generator
Zoledronic acid	Generator
2-(Imidazol-1-yl)-1-hydroxyethylidene-1,1-bisphosphonic acid	HMDB
Novartis brand OF zoledronic acid	HMDB
Zoledronic acid anhydrous	HMDB

Chemical Formula

C₅H₁₀N₂O₇P₂

Average Molecular Weight

272.0896

Monoisotopic Molecular Weight

271.996323708

IUPAC Name

[1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acid

Traditional Name

zoledronate

CAS Registry Number

118072-93-8

SMILES

OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O

InChI Identifier

InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)

InChI Key

XRASPMIURGNCCH-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
N-substituted imidazole
Heteroaromatic compound
Organophosphonic acid
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:46557 )
1,1-bis(phosphonic acid) (CHEBI:46557 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014543)
Membrane (HMDB: HMDB0014543)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Zoledronate Action Pathway (PathBank: SMP0000107)
Zoledronate Pathway (HMDB: HMDB0014543)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

bone density conservation agent (HMDB: HMDB0014543)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.27 g/L	Not Available
LogP	-4.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.27 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-3.9	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	0.66	ChemAxon
pKa (Strongest Basic)	6.67	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.16 m³·mol⁻¹	ChemAxon
Polarizability	20.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	158.642	31661259
DarkChem	[M-H]-	153.048	31661259
DeepCCS	[M+H]+	141.241	30932474
DeepCCS	[M-H]-	138.845	30932474
DeepCCS	[M-2H]-	172.122	30932474
DeepCCS	[M+Na]+	147.153	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	144.4	32859911
AllCCS	[M+Na-2H]-	144.8	32859911
AllCCS	[M+HCOO]-	145.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zoledronate	OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O	3720.6	Standard polar	33892256
Zoledronate	OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O	1859.8	Standard non polar	33892256
Zoledronate	OC(CN1C=CN=C1)(P(O)(O)=O)P(O)(O)=O	2714.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zoledronate,1TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O	2499.2	Semi standard non polar	33892256
Zoledronate,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O	2483.4	Semi standard non polar	33892256
Zoledronate,2TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C	2479.4	Semi standard non polar	33892256
Zoledronate,2TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C	2317.4	Standard non polar	33892256
Zoledronate,2TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C	3243.3	Standard polar	33892256
Zoledronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	2463.1	Semi standard non polar	33892256
Zoledronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	2357.2	Standard non polar	33892256
Zoledronate,2TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	3100.8	Standard polar	33892256
Zoledronate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C	2460.8	Semi standard non polar	33892256
Zoledronate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C	2340.1	Standard non polar	33892256
Zoledronate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C	3142.8	Standard polar	33892256
Zoledronate,3TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O)O[Si](C)(C)C	2453.3	Semi standard non polar	33892256
Zoledronate,3TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O)O[Si](C)(C)C	2335.3	Standard non polar	33892256
Zoledronate,3TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O)O[Si](C)(C)C	2964.9	Standard polar	33892256
Zoledronate,3TMS,isomer #2	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2480.4	Semi standard non polar	33892256
Zoledronate,3TMS,isomer #2	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2368.8	Standard non polar	33892256
Zoledronate,3TMS,isomer #2	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2915.3	Standard polar	33892256
Zoledronate,3TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2429.0	Semi standard non polar	33892256
Zoledronate,3TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2370.4	Standard non polar	33892256
Zoledronate,3TMS,isomer #3	C[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2899.5	Standard polar	33892256
Zoledronate,4TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2458.2	Semi standard non polar	33892256
Zoledronate,4TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2365.0	Standard non polar	33892256
Zoledronate,4TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2713.0	Standard polar	33892256
Zoledronate,4TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2403.0	Semi standard non polar	33892256
Zoledronate,4TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2371.2	Standard non polar	33892256
Zoledronate,4TMS,isomer #2	C[Si](C)(C)OP(=O)(O[Si](C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2679.1	Standard polar	33892256
Zoledronate,5TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2492.4	Semi standard non polar	33892256
Zoledronate,5TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2402.2	Standard non polar	33892256
Zoledronate,5TMS,isomer #1	C[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C)O[Si](C)(C)C)P(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2512.5	Standard polar	33892256
Zoledronate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O	2784.5	Semi standard non polar	33892256
Zoledronate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O	2753.3	Semi standard non polar	33892256
Zoledronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C(C)(C)C	2973.1	Semi standard non polar	33892256
Zoledronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C(C)(C)C	2720.6	Standard non polar	33892256
Zoledronate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O)O[Si](C)(C)C(C)(C)C	3448.5	Standard polar	33892256
Zoledronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	2964.9	Semi standard non polar	33892256
Zoledronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	2724.5	Standard non polar	33892256
Zoledronate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O)O	3374.9	Standard polar	33892256
Zoledronate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	2930.9	Semi standard non polar	33892256
Zoledronate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	2720.7	Standard non polar	33892256
Zoledronate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O)O[Si](C)(C)C(C)(C)C	3415.7	Standard polar	33892256
Zoledronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O)O[Si](C)(C)C(C)(C)C	3111.0	Semi standard non polar	33892256
Zoledronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O)O[Si](C)(C)C(C)(C)C	2840.0	Standard non polar	33892256
Zoledronate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O)O[Si](C)(C)C(C)(C)C	3244.8	Standard polar	33892256
Zoledronate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3148.9	Semi standard non polar	33892256
Zoledronate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2857.0	Standard non polar	33892256
Zoledronate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3193.9	Standard polar	33892256
Zoledronate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3094.4	Semi standard non polar	33892256
Zoledronate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2841.1	Standard non polar	33892256
Zoledronate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(O)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3211.3	Standard polar	33892256
Zoledronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3275.6	Semi standard non polar	33892256
Zoledronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2944.3	Standard non polar	33892256
Zoledronate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3050.5	Standard polar	33892256
Zoledronate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3233.4	Semi standard non polar	33892256
Zoledronate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2923.1	Standard non polar	33892256
Zoledronate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)C(O)(CN1C=CN=C1)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3032.4	Standard polar	33892256
Zoledronate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3444.7	Semi standard non polar	33892256
Zoledronate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3070.4	Standard non polar	33892256
Zoledronate,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CN1C=CN=C1)(P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)P(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2938.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zoledronate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9120000000-239c3921d9c0513b29bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zoledronate GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9010000000-350e054fb0333ac6c489	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zoledronate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zoledronate DI-ESI-qTof , Negative-QTOF	splash10-000i-0910000000-6c7cee1b60ea3968e2f7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 10V, Positive-QTOF	splash10-00di-0190000000-d743d302781bf9a387dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 20V, Positive-QTOF	splash10-001l-8910000000-89833833ce5df6ce7fbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 40V, Positive-QTOF	splash10-014i-9350000000-6a8817aebcf8b58c9872	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 10V, Negative-QTOF	splash10-00di-1290000000-3a385a1ab40b3030223a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 20V, Negative-QTOF	splash10-0fki-4690000000-90b5d47e0913184a3303	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 40V, Negative-QTOF	splash10-004i-9100000000-8fed5642f16554892c2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 10V, Positive-QTOF	splash10-00dl-0690000000-d8e121c2f8fde6d36c50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 20V, Positive-QTOF	splash10-00di-1490000000-73b24204457ff8cb45cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 40V, Positive-QTOF	splash10-00lr-9100000000-a6b7ed66230e1c22c0cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 10V, Negative-QTOF	splash10-0fk9-0090000000-39599d85059cab3fb733	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 20V, Negative-QTOF	splash10-0iu0-9220000000-54fc3ff7d337e2817e04	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zoledronate 40V, Negative-QTOF	splash10-03mi-9110000000-c37cf2658c6d4e001274	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Zoledronate Action Pathway		Not Available

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 DB00399	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00399	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00399

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zoledronic_Acid

METLIN ID

Not Available

PubChem Compound

68740

PDB ID

ZOL

ChEBI ID

46557

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

Reid IR, Brown JP, Burckhardt P, Horowitz Z, Richardson P, Trechsel U, Widmer A, Devogelaer JP, Kaufman JM, Jaeger P, Body JJ, Brandi ML, Broell J, Di Micco R, Genazzani AR, Felsenberg D, Happ J, Hooper MJ, Ittner J, Leb G, Mallmin H, Murray T, Ortolani S, Rubinacci A, Saaf M, Samsioe G, Verbruggen L, Meunier PJ: Intravenous zoledronic acid in postmenopausal women with low bone mineral density. N Engl J Med. 2002 Feb 28;346(9):653-61. [PubMed:11870242 ]
Durie BG, Katz M, Crowley J: Osteonecrosis of the jaw and bisphosphonates. N Engl J Med. 2005 Jul 7;353(1):99-102; discussion 99-102. [PubMed:16000365 ]
Lyles KW, Colon-Emeric CS, Magaziner JS, Adachi JD, Pieper CF, Mautalen C, Hyldstrup L, Recknor C, Nordsletten L, Moore KA, Lavecchia C, Zhang J, Mesenbrink P, Hodgson PK, Abrams K, Orloff JJ, Horowitz Z, Eriksen EF, Boonen S: Zoledronic acid and clinical fractures and mortality after hip fracture. N Engl J Med. 2007 Nov 1;357(18):1799-809. doi: 10.1056/NEJMoa074941. Epub 2007 Sep 17. [PubMed:17878149 ]

Enzymes

Enzyme Details

1. Geranylgeranyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name:: GGPS1
Uniprot ID:: O95749
Molecular weight:: 34870.625

References

Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH: Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. Proc Natl Acad Sci U S A. 2007 Jun 12;104(24):10022-7. Epub 2007 May 29. [PubMed:17535895 ]

Enzyme Details

2. Farnesyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
Specific function:: Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:: FDPS
Uniprot ID:: P14324
Molecular weight:: 48275.03

References

Dunford JE, Thompson K, Coxon FP, Luckman SP, Hahn FM, Poulter CD, Ebetino FH, Rogers MJ: Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates. J Pharmacol Exp Ther. 2001 Feb;296(2):235-42. [PubMed:11160603 ]
Glickman JF, Schmid A: Farnesyl pyrophosphate synthase: real-time kinetics and inhibition by nitrogen-containing bisphosphonates in a scintillation assay. Assay Drug Dev Technol. 2007 Apr;5(2):205-14. [PubMed:17477829 ]
Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH: Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases. Proc Natl Acad Sci U S A. 2007 Jun 12;104(24):10022-7. Epub 2007 May 29. [PubMed:17535895 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Yildiz M, Celik-Ozenci C, Akan S, Akan I, Sati L, Demir R, Savas B, Ozben T, Samur M, Ozdogan M, Artac M, Bozcuk H: Zoledronic acid is synergic with vinblastine to induce apoptosis in a multidrug resistance protein-1 dependent way: an in vitro study. Cell Biol Int. 2006 Mar;30(3):278-82. Epub 2006 Feb 2. [PubMed:16458542 ]

Showing metabocard for Zoledronate (HMDB0014543)

MOL for HMDB0014543 (Zoledronate)

3D MOL for HMDB0014543 (Zoledronate)

3D SDF for HMDB0014543 (Zoledronate)

3D-SDF for HMDB0014543 (Zoledronate)

PDB for HMDB0014543 (Zoledronate)

3D PDB for HMDB0014543 (Zoledronate)

SMILES for HMDB0014543 (Zoledronate)

INCHI for HMDB0014543 (Zoledronate)

Structure for HMDB0014543 (Zoledronate)

3D Structure for HMDB0014543 (Zoledronate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

Transporters

References