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Identification
NameGeldanamycin
Accession NumberDB02424  (EXPT01571)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
(4Z,6Z,8R,9R,10Z,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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Vinylogous ester
  • Vinylogous amide
  • Cyclic ketone
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Ketone
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Enamine
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9074
Blood Brain Barrier-0.8313
Caco-2 permeable-0.6156
P-glycoprotein substrateSubstrate0.5807
P-glycoprotein inhibitor IInhibitor0.8562
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.9493
CYP450 2C9 substrateNon-substrate0.8684
CYP450 2D6 substrateNon-substrate0.8444
CYP450 3A4 substrateSubstrate0.5922
CYP450 1A2 substrateNon-inhibitor0.8116
CYP450 2C9 substrateNon-inhibitor0.8498
CYP450 2D6 substrateNon-inhibitor0.8999
CYP450 2C19 substrateNon-inhibitor0.8016
CYP450 3A4 substrateNon-inhibitor0.9134
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9492
Ames testNon AMES toxic0.6172
CarcinogenicityNon-carcinogens0.9569
BiodegradationNot ready biodegradable0.7418
Rat acute toxicity2.3822 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9941
hERG inhibition (predictor II)Non-inhibitor0.9645
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00634 mg/mLALOGPS
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 Area163.48 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity152.68 m3·mol-1ChemAxon
Polarizability57.77 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
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-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

2. 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

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