geldanamycin
AlkaPlorer ID: AK006481
Synonym: '2-Azabicyclo16.3.1docosa-4,6,10,18,21-pentaene- 3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy- 4,10,12,16-tetramethyl-, 9-carbamate', 'Geldanamicin', 'GELDANAMYCIN', 'Antibiotic U 29135', 'Antibiotic (U-29,135)', 'geldanamycin', 'NSC 212518', 'Geldanamycin', 'NSC 122750'
IUPAC Name: [(4E,6Z,8R,9R,10E,12R,13S,14R,16R)-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
Structure
SMILES: COC1=C2C[C@@H](C)C[C@@H](OC)[C@@H](O)[C@H](C)/C=C(\C)[C@@H](OC(N)=O)[C@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O
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
InChIKey: QTQAWLPCGQOSGP-VKNBREQOSA-N
Reference
The description and antibiotic production of Streptomyces hygroscopicus var. geldanus.
PubChem CID: 5281885
LOTUS: LTS0268659
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces violaceusniger | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 560.6440000000002
TPSA？: 163.48
MolLogP？: 2.4084000000000003
Number of H-Donors: 3
Number of H-Acceptors: 9
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Acinetobacter baumannii | Acinetobacter baumannii | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Candida albicans | Candida albicans | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Cryptococcus neoformans | Cryptococcus neoformans | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Escherichia coli | Escherichia coli | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Homo sapiens | 786-0 | GI50 | 76.21 | nM | None |
| Homo sapiens | A498 | GI50 | 11271.97 | nM | None |
| Homo sapiens | A549 | GI50 | 5780.96 | nM | None |
| Homo sapiens | ACHN | GI50 | 155.96 | nM | None |
| Homo sapiens | BT-549 | GI50 | 650.13 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 1770.11 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 28.18 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 11.64 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 67.92 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 53.09 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 116.95 | nM | None |
| Homo sapiens | DU-145 | GI50 | 106.17 | nM | None |
| Homo sapiens | EKVX | GI50 | 6561.45 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 879.02 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 41.88 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 264.85 | nM | None |
| Homo sapiens | HEK293 | CC50 | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Homo sapiens | HL-60 | GI50 | 13.21 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 158.85 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 3380.65 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 111.69 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 2910.72 | nM | None |
| Homo sapiens | HT-29 | GI50 | 14.32 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 290.4 | nM | None |
| Homo sapiens | K562 | GI50 | 11.53 | nM | None |
| Homo sapiens | KM12 | GI50 | 454.99 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 26.55 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 66.53 | nM | None |
| Homo sapiens | LXFL 529 | GI50 | 26.73 | nM | None |
| Homo sapiens | M14 | GI50 | 106.17 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 118.85 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 43.95 | nM | None |
| Homo sapiens | MCF7 | GI50 | 19.82 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 42.07 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 30.9 | nM | None |
| Homo sapiens | MDA-N | GI50 | 21.63 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 19.91 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 10069.32 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 3564.51 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 30.9 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 8511.38 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 1485.94 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 35.97 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 212.81 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 2018.37 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 6870.68 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 61.38 | nM | None |
| Homo sapiens | PC-3 | GI50 | 121.9 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 137.72 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 81.85 | nM | None |
| Homo sapiens | RXF 631 | GI50 | 709.58 | nM | None |
| Homo sapiens | SF-268 | GI50 | 1011.58 | nM | None |
| Homo sapiens | SF-295 | GI50 | 9375.62 | nM | None |
| Homo sapiens | SF-539 | GI50 | 131.52 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 396.28 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 113.24 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 677.64 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 1042.32 | nM | None |
| Homo sapiens | SN12C | GI50 | 40.55 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 109.65 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 10209.39 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 5495.41 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 1035.14 | nM | None |
| Homo sapiens | SR | GI50 | 31.12 | nM | None |
| Homo sapiens | SW-620 | GI50 | 12.65 | nM | None |
| Homo sapiens | T47D | GI50 | 24.04 | nM | None |
| Homo sapiens | TK-10 | GI50 | 117.76 | nM | None |
| Homo sapiens | U-251 | GI50 | 2930.89 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 76.91 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 122.18 | nM | None |
| Homo sapiens | UO-31 | GI50 | 188.8 | nM | None |
| Homo sapiens | XF498 | GI50 | 78.7 | nM | None |
| Klebsiella pneumoniae | Klebsiella pneumoniae | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Mus musculus | P388 | GI50 | 15.0 | nM | None |
| Mus musculus | P388/ADR | GI50 | 211.84 | nM | None |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |
| Staphylococcus aureus | Staphylococcus aureus | MIC | 10000.0 | nM | 10.6019/CHEMBL4296183 |