N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.09,13]heptacosan-18-yl]hexadecanamide

• ChemBase ID: 154245
• Molecular Formular: C50H81N7O16
• Molecular Mass: 1036.21544
• Monoisotopic Mass: 1035.57397955
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]1C[C@H]([C@H](NC(=O)[C@@H]2[C@H]([C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2C[C@H](CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@@H](C)O)C)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@H](CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)[C@H](O)C)C[C@@H](C2)O)[C@@H]([C@H](c1ccc(cc1)O)O)O)[C@H](O)C)C
• InChI: InChI=1S/C50H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-36(63)51-33-24-35(62)46(69)55-48(71)40-41(64)27(2)25-57(40)50(73)38(29(4)59)53-47(70)39(43(66)42(65)30-19-21-31(60)22-20-30)54-45(68)34-23-32(61)26-56(34)49(72)37(28(3)58)52-44(33)67/h19-22,27-29,32-35,37-43,46,58-62,64-66,69H,5-18,23-26H2,1-4H3,(H,51,63)(H,52,67)(H,53,70)(H,54,68)(H,55,71)/t27-,28+,29+,32+,33-,34-,35+,37-,38-,39-,40-,41-,42-,43-,46+/m0/s1
• InChIKey: YKPHLXGEPNYRPY-ZIUFDZNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,^1^3]heptacosan-18-yl]hexadecanamide
• IUPAC Traditional name: N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-3,15-bis[(1R)-1-hydroxyethyl]-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0^9,^1^3]heptacosan-18-yl]hexadecanamide
• Synonyms: Aculeacin A

Database IDs

• CAS Number: 58814-86-1
• MDL Number: MFCD01674009
• PubChem SID: 162248384
• PubChem CID: 14315169

CALCULATED PROPERTIES

• Acid pKa: 9.457595
• H Acceptors: 16
• H Donor: 14
• LogD (pH = 5.5): -1.7367576
• LogD (pH = 7.4): -1.7404642
• Log P: -1.7367102
• Molar Refractivity: 260.8524 cm^3
• Polarizability: 103.50984 Å^3
• Polar Surface Area: 368.19 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble10 mg/mL; ethanol: soluble; methanol: soluble

Safety Information

• RTECS: AU2980000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Biological Source: from Aspergillus aculeatus
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C50H81N7O16

DETAILS

Sigma Aldrich - A7603

Biochem/physiol Actions
Aculeacin A is a lipopeptide that inhibits β-glucan synthesis in yeasts. The inhibition is due to the selective blockage of glucan synthase.
Aculeacin A, an amphophilic antibiotic, inhibits the biosynthesis of β-glucan by selective blockage of β(1→3) glucan synthase.
Application
Aculeacin A is used to study mutations that lead to antibiotic resistance in Saccharomyces cerevisiae 1, the inhibition of Candida albicans2, and the morphogenetic transformation of Candida albicans when treated 3.