Alvespimycin hydrochlorideProduct ingredient for Alvespimycin

Name
Alvespimycin hydrochloride
Drug Entry
Alvespimycin

Alvespimycin is a derivative of geldanamycin and heat shock protein (HSP) 90 inhibitor. It has been used in trials studying the treatment of solid tumor in various cancer as an antitumor agent. In comparison to the first HSP90 inhibitor tanespimycin, it exhibits some pharmacologically desirable properties such as reduced metabolic liability, lower plasma protein binding, increased water solubility, higher oral bioavailability, reduced hepatotoxicity and superior antitumor activity 1.

Accession Number
DBSALT002385
Structure
Synonyms
17-DMAG HCl / Alvespimycin HCl / Alvespimycin hydrochloride
External IDs
BMS-826476
UNII
612K359T69
CAS Number
467214-21-7
Weight
Average: 653.21
Monoisotopic: 652.3238923
Chemical Formula
C32H49ClN4O8
InChI Key
DFSYBWLNYPEFJK-IHLRWNDRSA-N
InChI
InChI=1S/C32H48N4O8.ClH/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8;/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40);1H/b11-9-,19-10+,21-16+;/t18-,20+,25+,26+,28-,30+;/m1./s1
IUPAC Name
(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-13-hydroxy-8,14-dimethoxy-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 hydrochloride
SMILES
Cl.CO[C@H]1C[C@H](C)CC2=C(NCCN(C)C)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
ChemSpider
21396132
ChEMBL
CHEMBL2105630
Predicted Properties
PropertyValueSource
Water Solubility0.0211 mg/mLALOGPS
logP1.84ALOGPS
logP1.85Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.78Chemaxon
pKa (Strongest Basic)8.56Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area169.52 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity172.38 m3·mol-1Chemaxon
Polarizability66.39 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon