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Identification
NameGeldanamycin
Accession NumberDB02424  (EXPT01571)
Typesmall molecule
Groupsexperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number30562-34-6
WeightAverage: 560.6359
Monoisotopic: 560.273380888
Chemical FormulaC29H40N2O9
InChI KeyQTQAWLPCGQOSGP-GBTDJJJQSA-N
InChI
InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9-,18-13-/t15-,17+,22+,23+,24+,26+/m0/s1
IUPAC Name
(8R,9R,12R,13R,14R,16S)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
SMILES
CO[C@@H]1C[C@@H](C)CC2=C(OC)C(=O)C=C(NC(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@H]1O)C2=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbonyl Compounds
SubclassKetones
Direct parentp-Quinones
Alternative parentsp-Benzoquinones; Secondary Carboxylic Acid Amides; Secondary Alcohols; Carbamic Acids and Derivatives; Ethers; Enamines; Carboxylic Acids; Polyamines
Substituentscarbamic acid derivative; carboxamide group; secondary carboxylic acid amide; secondary alcohol; ether; carboxylic acid derivative; polyamine; carboxylic acid; enamine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the p-quinones.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9074
Blood Brain Barrier - 0.8313
Caco-2 permeable - 0.6156
P-glycoprotein substrate Substrate 0.5807
P-glycoprotein inhibitor I Inhibitor 0.8562
P-glycoprotein inhibitor II Inhibitor 0.8387
Renal organic cation transporter Non-inhibitor 0.9493
CYP450 2C9 substrate Non-substrate 0.8684
CYP450 2D6 substrate Non-substrate 0.8444
CYP450 3A4 substrate Substrate 0.5922
CYP450 1A2 substrate Non-inhibitor 0.8116
CYP450 2C9 substrate Non-inhibitor 0.8498
CYP450 2D6 substrate Non-inhibitor 0.8999
CYP450 2C19 substrate Non-inhibitor 0.8016
CYP450 3A4 substrate Non-inhibitor 0.9134
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9492
Ames test Non AMES toxic 0.6172
Carcinogenicity Non-carcinogens 0.9569
Biodegradation Not ready biodegradable 0.7418
Rat acute toxicity 2.3822 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9941
hERG inhibition (predictor II) Non-inhibitor 0.9645
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility6.34e-03 g/lALOGPS
logP2.54ALOGPS
logP2.15ChemAxon
logS-5ALOGPS
pKa (strongest acidic)12.77ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count3ChemAxon
polar surface area163.48ChemAxon
rotatable bond count5ChemAxon
refractivity152.68ChemAxon
polarizability57.77ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Richard Hutchinson, “Recombinant polynucleotides encoding pro-geldanamycin producing polyketide synthase and accessory proteins, and uses thereof.” U.S. Patent US20040077058, issued April 22, 2004.

US20040077058
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC11222
PubChem Compound46936377
PubChem Substance46505674
ChemSpider3342
BindingDB50227098
Therapeutic Targets DatabaseDCL000325
PharmGKBPA152031327
HETGDM
WikipediaGeldanamycin
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Heat shock protein HSP 90-beta

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Heat shock protein HSP 90-beta P08238 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Heat shock protein HSP 90-alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Heat shock protein HSP 90-alpha P07900 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18