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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014415
Secondary Accession Numbers
  • HMDB14415
Metabolite Identification
Common NameIsradipine
DescriptionIsradipine belongs to the dihydropyridine (DHP) class of calcium channel blockers (CCBs), the most widely used class of CCBs. It is structurally related to felodipine, nifedipine, and nimodipine and is the most potent calcium-channel blocking agent of the DHP class. Isradipine binds to calcium channels with high affinity and specificity and inhibits calcium flux into cardiac and arterial smooth muscle cells. It exhibits greater selectivity towards arterial smooth muscle cells owing to alternative splicing of the alpha-1 subunit of the channel and increased prevalence of inactive channels in smooth muscle cells. Isradipine may be used to treat mild to moderate essential hypertension.
Structure
Data?1582753177
Synonyms
ValueSource
DynacircKegg
(+/-)-isradipineHMDB
IsradipinHMDB
IsrodipineHMDB
Isradipine, (+-)-isomerMeSH, HMDB
Isradipine, (R)-isomerMeSH, HMDB
Isradipine, (S)-isomerMeSH, HMDB
LomirMeSH, HMDB
Chemical FormulaC19H21N3O5
Average Molecular Weight371.3871
Monoisotopic Molecular Weight371.148120797
IUPAC Name3-methyl 5-propan-2-yl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Traditional Nameisradipine
CAS Registry Number75695-93-1
SMILES
COC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C
InChI Identifier
InChI=1S/C19H21N3O5/c1-9(2)26-19(24)15-11(4)20-10(3)14(18(23)25-5)16(15)12-7-6-8-13-17(12)22-27-21-13/h6-9,16,20H,1-5H3
InChI KeyHMJIYCCIJYRONP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxadiazoles. These are organic compounds containing a benzene fused to an oxadiazole ring (a five-membered ring with two carbon atoms, one nitrogen atom, and one oxygen atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxadiazoles
Sub ClassNot Available
Direct ParentBenzoxadiazoles
Alternative Parents
Substituents
  • Benzoxadiazole
  • Dihydropyridinecarboxylic acid derivative
  • Dihydropyridine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Hydropyridine
  • Azole
  • Heteroaromatic compound
  • Furazan
  • Vinylogous amide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Oxadiazole
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Secondary amine
  • Azacycle
  • Enamine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point168 - 170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP2.901Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP3ALOGPS
logP2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)5.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.55 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.08 m³·mol⁻¹ChemAxon
Polarizability37.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.031661259
DarkChem[M-H]-182.20331661259
DeepCCS[M-2H]-218.58130932474
DeepCCS[M+Na]+194.17530932474
AllCCS[M+H]+186.832859911
AllCCS[M+H-H2O]+184.032859911
AllCCS[M+NH4]+189.432859911
AllCCS[M+Na]+190.132859911
AllCCS[M-H]-191.332859911
AllCCS[M+Na-2H]-191.432859911
AllCCS[M+HCOO]-191.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsradipineCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C3651.6Standard polar33892256
IsradipineCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C2778.2Standard non polar33892256
IsradipineCOC(=O)C1=C(C)NC(C)=C(C1C1=CC=CC2=NON=C12)C(=O)OC(C)C2787.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isradipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C122898.2Semi standard non polar33892256
Isradipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C122498.3Standard non polar33892256
Isradipine,1TMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C123977.0Standard polar33892256
Isradipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C123093.5Semi standard non polar33892256
Isradipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C122716.0Standard non polar33892256
Isradipine,1TBDMS,isomer #1COC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C123969.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6059000000-e9ec514baf6b881462eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isradipine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine LC-ESI-qTof , Positive-QTOFsplash10-0006-0009000000-3c8fe8c9d5e94c0182992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine LC-ESI-qTof , Positive-QTOFsplash10-03dl-2589000000-e01ef029445c948c93e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine , positive-QTOFsplash10-0006-0009000000-3c8fe8c9d5e94c0182992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine , positive-QTOFsplash10-03dl-2589000000-e01ef029445c948c93e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine 35V, Negative-QTOFsplash10-014i-1910000000-dfed2a9ad69e197388ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isradipine 35V, Positive-QTOFsplash10-08gl-0093000000-018aae73f171426e97862021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 10V, Positive-QTOFsplash10-0006-0019000000-14fbaf7e209b164eca312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 20V, Positive-QTOFsplash10-01wb-1094000000-f17e6d7b6c23adad32d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 40V, Positive-QTOFsplash10-001i-1192000000-f7640fb5efbe178b44182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 10V, Negative-QTOFsplash10-00di-1029000000-a657ce350be64e5e10cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 20V, Negative-QTOFsplash10-05gi-3169000000-482100e723136208aa672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 40V, Negative-QTOFsplash10-0aor-6191000000-85fa9ee77cf0b2b9a9fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 10V, Negative-QTOFsplash10-00di-0109000000-16c47c66d4fad17b54542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 20V, Negative-QTOFsplash10-05fr-2019000000-e3409ae5fd7b715f63602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 40V, Negative-QTOFsplash10-014i-0393000000-894b314cbe04d7da31272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 10V, Positive-QTOFsplash10-03k9-0009000000-91e2afb1e32f59d7a22e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 20V, Positive-QTOFsplash10-0h3r-0094000000-90ceb2e95c063a9a89532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isradipine 40V, Positive-QTOFsplash10-0fka-1292000000-d08a6d4825f5eb1d6fab2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00270 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00270 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00270
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3652
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsradipine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fletcher H, Roberts G, Mullings A, Forrester T: An open trial comparing isradipine with hydralazine and methyl dopa in the treatment of patients with severe pre-eclampsia. J Obstet Gynaecol. 1999 May;19(3):235-8. [PubMed:15512286 ]
  2. Johnson BA, Roache JD, Ait-Daoud N, Wallace C, Wells L, Dawes M, Wang Y: Effects of isradipine, a dihydropyridine-class calcium-channel antagonist, on d-methamphetamine's subjective and reinforcing effects. Int J Neuropsychopharmacol. 2005 Jun;8(2):203-13. [PubMed:15850499 ]
  3. Ganz M, Mokabberi R, Sica DA: Comparison of blood pressure control with amlodipine and controlled-release isradipine: an open-label, drug substitution study. J Clin Hypertens (Greenwich). 2005 Apr;7(4 Suppl 1):27-31. [PubMed:15858400 ]
  4. Hattori T, Wang PL: Calcium antagonist isradipine-induced calcium influx through nonselective cation channels in human gingival fibroblasts. Eur J Med Res. 2006 Mar 27;11(3):93-6. [PubMed:16751108 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1D gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:
CACNA1D
Uniprot ID:
Q01668
Molecular weight:
245138.8
References
  1. Koschak A, Reimer D, Huber I, Grabner M, Glossmann H, Engel J, Striessnig J: alpha 1D (Cav1.3) subunits can form l-type Ca2+ channels activating at negative voltages. J Biol Chem. 2001 Jun 22;276(25):22100-6. Epub 2001 Apr 2. [PubMed:11285265 ]
  2. Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J: Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. Mol Pharmacol. 2009 Feb;75(2):407-14. doi: 10.1124/mol.108.049981. Epub 2008 Nov 24. [PubMed:19029287 ]
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1C gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1C subunit play an important role in excitation-contraction coupling in the heart. The various isoforms display marked differences in the sensitivity to DHP compounds. Binding of calmodulin or CABP1 at the same regulatory sites results in an opposit effects on the channel function
Gene Name:
CACNA1C
Uniprot ID:
Q13936
Molecular weight:
248974.1
References
  1. Berjukow S, Marksteiner R, Gapp F, Sinnegger MJ, Hering S: Molecular mechanism of calcium channel block by isradipine. Role of a drug-induced inactivated channel conformation. J Biol Chem. 2000 Jul 21;275(29):22114-20. [PubMed:10766758 ]
  2. Hitzl M, Striessnig J, Neuhuber B, Flucher BE: A mutation in the beta interaction domain of the Ca(2+) channel alpha(1C) subunit reduces the affinity of the (+)-[(3)H]isradipine binding site. FEBS Lett. 2002 Jul 31;524(1-3):188-92. [PubMed:12135765 ]
  3. Zuhlke RD, Bouron A, Soldatov NM, Reuter H: Ca2+ channel sensitivity towards the blocker isradipine is affected by alternative splicing of the human alpha1C subunit gene. FEBS Lett. 1998 May 8;427(2):220-4. [PubMed:9607315 ]
General function:
Involved in metal ion binding
Specific function:
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Plays an important role in excitation-contraction coupling
Gene Name:
CACNA2D1
Uniprot ID:
P54289
Molecular weight:
124566.9
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in calcium channel activity
Specific function:
The alpha-2/delta subunit of voltage-dependent calcium channels regulates calcium current density and activation/inactivation kinetics of the calcium channel. Acts as a regulatory subunit for P/Q-type calcium channel (CACNA1A), N-type (CACNA1B), L-type (CACNA1C OR CACNA1D) and possibly T-type (CACNA1G). Overexpression induces apoptosis
Gene Name:
CACNA2D2
Uniprot ID:
Q9NY47
Molecular weight:
129875.2
References
  1. Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
  2. Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361 ]
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1H gives rise to T-type calcium currents. T-type calcium channels belong to the "low-voltage activated (LVA)" group and are strongly blocked by nickel and mibefradil. A particularity of this type of channels is an opening at quite negative potentials, and a voltage-dependent inactivation. T-type channels serve pacemaking functions in both central neurons and cardiac nodal cells and support calcium signaling in secretory cells and vascular smooth muscle. They may also be involved in the modulation of firing patterns of neurons which is important for information processing as well as in cell growth processes
Gene Name:
CACNA1H
Uniprot ID:
O95180
Molecular weight:
259160.2
References
  1. Cohen CJ, Spires S, Van Skiver D: Block of T-type Ca channels in guinea pig atrial cells by antiarrhythmic agents and Ca channel antagonists. J Gen Physiol. 1992 Oct;100(4):703-28. [PubMed:1281221 ]
  2. Perez-Reyes E, Van Deusen AL, Vitko I: Molecular pharmacology of human Cav3.2 T-type Ca2+ channels: block by antihypertensives, antiarrhythmics, and their analogs. J Pharmacol Exp Ther. 2009 Feb;328(2):621-7. doi: 10.1124/jpet.108.145672. Epub 2008 Oct 30. [PubMed:18974361 ]
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1S gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing the alpha-1S subunit play an important role in excitation-contraction coupling in skeletal muscle
Gene Name:
CACNA1S
Uniprot ID:
Q13698
Molecular weight:
212348.1
References
  1. Peterson BZ, Catterall WA: Allosteric interactions required for high-affinity binding of dihydropyridine antagonists to Ca(V)1.1 Channels are modulated by calcium in the pore. Mol Pharmacol. 2006 Aug;70(2):667-75. Epub 2006 May 4. [PubMed:16675661 ]
General function:
Involved in voltage-gated calcium channel activity
Specific function:
The beta subunit of voltage-dependent calcium channels contributes to the function of the calcium channel by increasing peak calcium current, shifting the voltage dependencies of activation and inactivation, modulating G protein inhibition and controlling the alpha-1 subunit membrane targeting
Gene Name:
CACNB2
Uniprot ID:
Q08289
Molecular weight:
73579.9
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]