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30562-34-6

Basic Information
CAS No.: 30562-34-6
Name: Geldanamycin
Article Data: 1
Cas Database
Molecular Structure:
Molecular Structure of 30562-34-6 (Geldanamycin)
Formula: C29H40N2O9
Molecular Weight: 560.645
Synonyms: 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione,9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate (8CI);(+)-Geldanamycin;2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione,9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-,[8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-;NSC 122750;NSC 212518;[8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione;
EINECS: 999-999-2
Density: 1.23 g/cm3
Melting Point: 255 °C
Boiling Point: 783.9 °C at 760 mmHg
Flash Point: 427.9 °C
Solubility: DMSO: soluble
Appearance: yellow to orange powder
Hazard Symbols: ToxicT, IrritantXi
Risk Codes: 36/37/38
Safety: 26-27-36/37/39
Transport Information: N/A
PSA: 163.48000
LogP: 3.43750
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Specification

The Geldanamycin, with the CAS registry number 30562-34-6, belongs to the product categories of Antibiotics; Antibiotics for Research and Experimental Use; Antitumors for Research and Experimental Use; Biochemistry; Macrolides (Antibiotics for Research and Experimental Use); Others (Antibiotics for Research and Experimental Use) ;Amines; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Heat Shock Protein 90. Its IUPAC name is called [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate. This chemical's classification codes are Anti-Infective Agents; Antibiotics, antineoplastic; Antineoplastic Agents; Antiviral Agents; Cysteine proteinase inhibitors; Drug / Therapeutic Agent; Enzyme inhibitors; Mutation data; Natural Product; Protease Inhibitors. The product should be sealed at temperature of -20 °C.

Physical properties of Geldanamycin: (1)ACD/LogP: 2.62; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 2; (5)ACD/BCF (pH 5.5): 19; (6)ACD/BCF (pH 7.4): 18; (7)ACD/KOC (pH 5.5): 291; (8)ACD/KOC (pH 7.4): 267; (9)#H bond acceptors: 11; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.559; (13)Molar Refractivity: 146.759 cm3; (14)Molar Volume: 454.454 cm3; (15)Surface Tension: 51.436 dyne/cm; (16)Density: 1.234 g/cm3; (17)Flash Point: 427.864 °C; (18)Enthalpy of Vaporization: 129.976 kJ/mol; (19)Boiling Point: 783.862 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Geldanamycin is a benzoquinone ansamycin antibiotic that binds to Hsp90 (Heat Shock Protein 90) and alters its function. Geldanamycin induces the degradation of proteins that are mutated in tumor cells such as v-Src, Bcr-Abl and p53 preferentially over their normal cellular counterparts.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: NC(=O)O[C@H]1C(/C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)C\C2=C(/OC)C(=O)\C=C(\NC(=O)C(\C)=C\C=C/[C@@H]1OC)C2=O
(2)InChI: InChI=1/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
(3)InChIKey: QTQAWLPCGQOSGP-KSRBKZBZBP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intravenous > 4200ug/kg (4.2mg/kg)   Cancer Chemotherapy and Pharmacology. Vol. 36, Pg. 305, 1995.
mouse LD intravenous > 50mg/kg (50mg/kg)   Cancer Chemotherapy and Pharmacology. Vol. 36, Pg. 305, 1995.
mouse LD50 intraperitoneal 1mg/kg (1mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
rat LD50 oral 2500mg/kg (2500mg/kg)   Journal of Antibiotics. Vol. 23, Pg. 442, 1970.