Grisellimycin

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Basic information

CAS: 26034-16-2
Standard SMILES: CCC(C)[C@@H]1NC(=O)[C@H]2C[C@@H](C)CN2C(=O)[C@H](C(C)CC)NC(=O)[C@@H](N(C)C(=O)C2C[C@@H](C)CN2C(=O)[C@H](C(C)C)N(C)C(C)=O)[C@@H](C)OC(=O)CNC(=O)[C@@H](C(C)CC)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)N(C)C1=O
InChIKey: BVCBJSHZCAWDPE-RENOUVQNSA-N
Molecular formula: C57H96N10O12
Average molar mass: 1,113.4 g/mol
Monoisotopic mass: 1,112.72091854

Names & identifiers

Preferred name: Grisellimycin
IUPAC: (4R)-1-[(2S)-2-[acetyl(methyl)amino]-3-methylbutanoyl]-N,4-dimethyl-N-[(3R,6S,9R,11R,15S,18S,19R,25R,28S)-6,15,25-tri(butan-2-yl)-4,11,19,26-tetramethyl-2,5,8,14,17,21,24,27-octaoxo-3-propan-2-yl-20-oxa-1,4,7,13,16,23,26-heptazatricyclo[26.3.0.09,13]hentriacontan-18-yl]pyrrolidine-2-carboxamide
English name: N-(N-Methyl-N-acetyl-L-Val-4β-methyl-L-Pro-)N-methylcyclo[L-Thr*-L-Leu-4β-methyl-L-Pro-L-Leu-N-methyl-L-Val-L-Pro-N-methyl-D-Leu-Gly-]
Molecular formula: C57H96N10O12
Molecular weight: 1113.45

Names & synonyms

GrisellimycinGrizelimycinGrisellimycin BNSC 246122RP-11072-BGriselimycinRP11072-BRP 11072-BN-Methyl-N-[N-methyl-N-Ac-L-Val-4β-methyl-L-Pro-]cyclo[L-Thr*-L-Leu-4β-methyl-L-Pro-L-Leu-N-methyl-L-Val-L-Pro-N-methyl-D-Leu-Gly-]N-(N-Methyl-N-acetyl-L-Val-4β-methyl-L-Pro-)N-methylcyclo[L-Thr*-L-Leu-4β-methyl-L-Pro-L-Leu-N-methyl-L-Val-L-Pro-N-methyl-D-Leu-Gly-N-(N-Methyl-N-acetyl-L-Val-4β-methyl-L-Pro-)N-methylcyclo[L-Thr*-L-Leu-4β-methyl-L-Pro-L-Leu-N-methyl-L-Val-L-Pro-N-methyl-D-Leu-Gly-]Glycine, N-acetyl-N-methyl-L-valyl-(4R)-4-methyl-L-prolyl-N-methyl-L-threonyl-L-leucyl-(4R)-4-methyl-L-prolyl-L-leucyl-N-methyl-L-valyl-L-prolyl-N-methyl-D-leucyl-, (10→3)-lactone

Database identifiers

CAS: 26034-16-2
PubChem CID: 72535

Properties

Computed structural properties

XLogP: 5.4
Topological polar surface area: 256 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 12
Rotatable bonds: 12
Heavy atoms: 79
Formal charge: 0
Complexity: 2,260

Physicochemical properties

Melting point: 266 · 266-268 °C
Boiling point: 1245.5 · 1245.5±65.0 °C(Predicted)
Density: 1.2 · 1.20±0.1 g/cm3(Predicted)
pka: 12.99 · 12.99±0.70(Predicted)
EWG's Food Scores: 1 · 1

Chemistry & industry

Applications

UsesGriselimycin is a compound with antituberculosis activity that exhibits good in vitro and in vivo activity against sensitive and resistant Mycobacterium tuberculosis, and its cyclohexyl derivative has high transformative potential.

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Compound notes

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