Tanespimycin (CHEM018939)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:41:08 UTC
Update Date2016-11-09 01:15:53 UTC
Accession NumberCHEM018939
Identification
Common NameTanespimycin
ClassSmall Molecule
DescriptionA 19-membered macrocyle that is geldanamycin in which the methoxy substituent attached to the benzoquinone moiety has been replaced by an allylamino group. It is a potent inhibitor of heat shock protein 90 (Hsp90). A less toxic analogue than geldanamycin, it induces apoptosis and displays antitumour effects.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
17-(Allylamino)-17-demethoxygeldanamycinChEBI
17-(Allylamino)geldanamycinChEBI
17-AAGChEBI
17-AllylaminogeldanamycinChEBI
17-Demethoxy-17-(2-propenylamino)geldanamycinChEBI
17-Demethoxy-17-allylamino geldanamycinChEBI
17-N-Allylamino-17-demethoxygeldanamycinChEBI
17AAGChEBI
NSC 330507ChEBI
NSC-330507ChEBI
TanespimycinaChEBI
TanespimycineChEBI
TanespimycinumChEBI
17-Allylamino-17-demethoxygeldanamycin hydroquinone saltMeSH
IPI-504MeSH
IPI-493MeSH
17-Allylamino-17-demethoxygeldanamycin hydroquinoneMeSH
17-(Allylamino)-17-demethoxy-geldanamycinMeSH
IPI 504MeSH
IPI 493MeSH
17-Allyl-aminogeldanamycinMeSH
17-Allylamino-geldanamycinMeSH
17-Allylamino-17-demethoxygeldanamycinMeSH
Retaspimycin hydrochlorideMeSH
Chemical FormulaC31H43N3O8
Average Molecular Mass585.698 g/mol
Monoisotopic Mass585.305 g/mol
CAS Registry Number75747-14-7
IUPAC Name{[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-3,13-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-19-[(prop-2-en-1-yl)amino]-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid
Traditional NameAAG
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(NCC=C)C(=O)C=C(N=C(O)\C(C)=C\1/[H])C2=O)OC
InChI IdentifierInChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1
InChI KeyAYUNIORJHRXIBJ-TXHRRWQRSA-N
Chemical Taxonomy
Description 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 amide
  • Carbamic acid ester
  • Amino acid or derivatives
  • Carboxamide group
  • Ketone
  • Lactam
  • Carbonic acid derivative
  • Secondary alcohol
  • Cyclic ketone
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Dialkyl ether
  • Secondary aliphatic amine
  • Enamine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0072 g/LALOGPS
logP2.53ALOGPS
logP1.52ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-2.9ChemAxon
pKa (Strongest Basic)11.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity175.25 m³·mol⁻¹ChemAxon
Polarizability61.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ko-2000090000-80400e0f67a908654e82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-4000090000-076b30aaab45634e1e34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9121130000-7b50f261b5e13fe91c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-8000090000-d2c9ad0c41cbdaf1ae18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000060000-0790f5184b74b931c570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9001100000-cb71a91c12b9c2590d40Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB05134
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link17-N-Allylamino-17-demethoxygeldanamycin
Chemspider IDNot Available
ChEBI ID64153
PubChem Compound ID6505803
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20646760
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20652703
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20683637
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21219297
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21283735
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21454186
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21534941
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21558407
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21594721
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21670086
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21791475
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21856392
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22047770
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22209975
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22377218
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22621282
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23564374
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24317439
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25096912
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=25633180
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25952464
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=26277605
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=26408708
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=26872308
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=26913406
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=26922527
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=27045471