(2S)-2-[(4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido]-6-octadecanamidohexanoic acid

• ChemBase ID: 132899
• Molecular Formular: C43H78N6O13
• Molecular Mass: 887.11182
• Monoisotopic Mass: 886.56268659
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)CC[C@H](C(=O)N)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@@H]([C@H](OC([C@@H]1NC(=O)C)O)CO)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)CC[C@H](C(=O)N)NC(=O)[C@@H](NC(=O)[C@H](O[C@@H]1[C@@H](NC(=O)C)C(O)O[C@@H]([C@H]1O)CO)C)C
• InChI: InChI=1S/C43H78N6O13/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-34(52)45-26-21-20-22-32(42(58)59)48-35(53)25-24-31(39(44)55)49-40(56)28(2)46-41(57)29(3)61-38-36(47-30(4)51)43(60)62-33(27-50)37(38)54/h28-29,31-33,36-38,43,50,54,60H,5-27H2,1-4H3,(H2,44,55)(H,45,52)(H,46,57)(H,47,51)(H,48,53)(H,49,56)(H,58,59)/t28-,29+,31+,32-,33+,36+,37+,38+,43?/m0/s1
• InChIKey: FKHUGQZRBPETJR-FZKCHLSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido]-6-octadecanamidohexanoic acid
• IUPAC Traditional name: (2S)-2-[(4R)-4-carbamoyl-4-[(2S)-2-[(2R)-2-{[(3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanamido]-6-octadecanamidohexanoic acid
• Synonyms: Muroctasin; Romurtide; N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys

Database IDs

• CAS Number: 78113-36-7
• MDL Number: MFCD00871261
• PubChem SID: 162227176; 24890471
• PubChem CID: 6917906

CALCULATED PROPERTIES

• Acid pKa: 3.6667876
• H Acceptors: 13
• H Donor: 10
• LogD (pH = 5.5): -0.07522818
• LogD (pH = 7.4): -1.5629301
• Log P: 1.755661
• Molar Refractivity: 227.2571 cm^3
• Polarizability: 90.4234 Å^3
• Polar Surface Area: 305.04 Å^2
• Rotatable Bonds: 35
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: OL5545000
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A0936

Biochem/physiol Actions
Antibiotic peptide.
N-Acetylmuramyl-Ala-D-isoglutaminyl-Nε-stearoyl-Lys, Romurtide, a muramyl dipeptide analogue, is a granulocyte-macrophage colony-stimulating factor and a TNF-α inducer.