(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2S)-3-carbamoyl-2-[(2S)-2-decanamido-3-[(2,4,5,6,7-2H5)-1H-indol-3-yl]propanamido]propanamido]propanoic acid

• ChemBase ID: 165409
• Molecular Formular: C72H101N17O26
• Molecular Mass: 1620.67064
• Monoisotopic Mass: 1619.71036644
• SMILES: C1(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](N1)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)c1ccccc1N)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCCCCCCCC)Cc1c2c(cccc2)[nH]c1)CC(=O)N)CC(=O)O)CCCN)CC(=O)O)C
• Canonical SMILES: NCCC[C@@H]1NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)CCCCCCCCC)CC(=O)N)CC(=O)O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CC(=O)O)C)CC(=O)O)CO)[C@@H](CC(=O)O)C)CC(=O)c1ccccc1N
• InChI: InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43+,44+,45+,46+,47+,48+,49+,50-,60+,61+/m1/s1
• InChIKey: DOAKLVKFURWEDJ-RWDRXURGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2S)-3-carbamoyl-2-[(2S)-2-decanamido-3-[(2,4,5,6,7-^2H₅)-1H-indol-3-yl]propanamido]propanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2S)-3-carbamoyl-2-[(2S)-2-decanamido-3-[(2,4,5,6,7-^2H₅)-1H-indol-3-yl]propanamido]propanamido]propanoic acid
• Synonyms: Ly-146032-d5 Trifluoroacetic Salt; Cidecin-d5 Trifluoroacetic Salt; Cubicin-d5 Trifluoroacetic Salt; Daptomycin-d5 Trifluoroacetic Acid Salt, Technical Grade(d5 major; contains D0)

Database IDs

• PubChem SID: 162259542
• PubChem CID: 71315187

CALCULATED PROPERTIES

• Acid pKa: 2.9766474
• H Acceptors: 27
• H Donor: 22
• LogD (pH = 5.5): -14.167885
• LogD (pH = 7.4): -18.900747
• Log P: -9.365402
• Molar Refractivity: 393.5654 cm^3
• Polarizability: 155.07701 Å^3
• Polar Surface Area: 702.02 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Brown Solid
• Melting Point: 145-148°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D193352

Labelled Daptomycin (D193350). Cyclic lipopeptide antibiotic derived from a fermentation product of Streptomyces roseosporus; disrupts plasma membrane function in gram-positive bacteria. Antibacterial.

REFERENCES

• Allen, N.E., et al.: Antimicrob. Agents Chemother., 31, 1093 (1987)
• Tully, F.P., et al.: Expert Opin. Invest. Drugs, 8, 1223 (1987)