(3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,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-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid

• ChemBase ID: 154366
• Molecular Formular: C72H101N17O26
• Molecular Mass: 1620.67064
• Monoisotopic Mass: 1619.71036644
• SMILES: CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H]1[C@H](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](NC(=O)[C@H](NC(=O)CNC1=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)c1ccccc1N)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-FAZHXZQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,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-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(3S,6S,9R,15S,18R,21S,24R,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-[(2R)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid
• Synonyms: Dapcin; Daptomycin

Database IDs

• CAS Number: 103060-53-3
• PubChem SID: 162248505
• PubChem CID: 71311849

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: 155.05566 Å^3
• Polar Surface Area: 702.02 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; methanol: soluble

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C72H101N17O26

DETAILS

Sigma Aldrich - D2446

Biochem/physiol Actions
Cyclic lipopeptide antibiotic effective against gram-positive bacteria. Derived from a fermentation product of Streptomyces sp. Its distinct mechanism of action, disrupting plamsa membrane function, makes it useful against resistant bacteria. Potential therapy for Staphylococcus aureus infections, including MRSA (methicillin-resistant Staphylococcus aureus).
Daptomycin disrupts plasma membrane function, which makes it useful against resistant bacteria. It is thought to cause rapid depolarization thereby inhibiting protein, DNA and RNA synthesis.
Application
Daptomycin is a cyclic lipopeptide antibiotic effective against gram-positive bacteria. It is derived from a fermentation product of Streptomyces sp. It is useful against resistant bacteria. It is a potential therapy for Staphylococcus aureus infections1, including MRSA (methicillin-resistant Staphylococcus aureus). It has also been studied as a potential therapy for Streptococcus pneumoniae infections 2. It has been used to study the impact of sarA on daptomycin susceptibility of Staphylococcus aureus.3