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Identification
NameGeldanamycin
Accession NumberDB02424  (EXPT01571)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIZ3K3VJ16KU
CAS number30562-34-6
WeightAverage: 560.6359
Monoisotopic: 560.273380888
Chemical FormulaC29H40N2O9
InChI KeyQTQAWLPCGQOSGP-KSRBKZBZSA-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+/m1/s1
IUPAC Name
{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid
SMILES
[H]/C1=C([H])/[C@]([H])(OC)[C@@]([H])(OC(O)=N)\C(C)=C([H])\[C@]([H])(C)[C@@]([H])(O)[C@]([H])(C[C@]([H])(C)CC2=C(OC)C(=O)C=C(N=C(O)\C(C)=C\1/[H])C2=O)OC
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 Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
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 inhibitorNon-inhibitor0.8498
CYP450 2D6 inhibitorNon-inhibitor0.8999
CYP450 2C19 inhibitorNon-inhibitor0.8016
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00618 mg/mLALOGPS
logP2.39ALOGPS
logP3.76ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)4.54ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area167.96 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity164.41 m3·mol-1ChemAxon
Polarizability57.62 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Geldanamycin.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Geldanamycin.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Geldanamycin.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Geldanamycin.
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Geldanamycin.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Geldanamycin.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Geldanamycin.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Geldanamycin.
BevacizumabBevacizumab may increase the cardiotoxic activities of Geldanamycin.
BoceprevirThe serum concentration of Geldanamycin can be decreased when it is combined with Boceprevir.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Geldanamycin.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Geldanamycin.
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Geldanamycin.
CarbamazepineThe metabolism of Geldanamycin can be increased when combined with Carbamazepine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Geldanamycin.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Geldanamycin.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Geldanamycin.
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Geldanamycin.
CyclophosphamideThe risk or severity of adverse effects can be increased when Geldanamycin is combined with Cyclophosphamide.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Geldanamycin.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Geldanamycin.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Geldanamycin.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Geldanamycin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Geldanamycin.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Geldanamycin.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Geldanamycin.
DigoxinDigoxin may decrease the cardiotoxic activities of Geldanamycin.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Geldanamycin.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Geldanamycin.
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Geldanamycin.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Geldanamycin.
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Geldanamycin.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Geldanamycin.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Geldanamycin.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Geldanamycin.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Geldanamycin.
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Geldanamycin.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Geldanamycin.
GarlicThe serum concentration of Geldanamycin can be decreased when it is combined with Garlic.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Geldanamycin.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Geldanamycin.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Geldanamycin.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Geldanamycin.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Geldanamycin.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Geldanamycin.
OuabainOuabain may decrease the cardiotoxic activities of Geldanamycin.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Geldanamycin.
PethidineThe risk or severity of adverse effects can be increased when Geldanamycin is combined with Pethidine.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Geldanamycin.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Geldanamycin.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Geldanamycin.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Geldanamycin.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Geldanamycin.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Geldanamycin.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Geldanamycin.
St. John's WortThe metabolism of Geldanamycin can be increased when combined with St. John's Wort.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Geldanamycin.
TemsirolimusThe risk or severity of adverse effects can be increased when Geldanamycin is combined with Temsirolimus.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Geldanamycin.
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Geldanamycin.
TipranavirThe serum concentration of Geldanamycin can be decreased when it is combined with Tipranavir.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Geldanamycin.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Geldanamycin.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Geldanamycin.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Geldanamycin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Tpr domain binding
Specific Function:
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle that is linked to its ATPase activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with v...
Gene Name:
HSP90AA1
Uniprot ID:
P07900
Molecular Weight:
84659.015 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Utp binding
Specific Function:
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle that is linked to its ATPase activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with v...
Gene Name:
HSP90AB1
Uniprot ID:
P08238
Molecular Weight:
83263.475 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23