(2S)-2-[(1R,2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-9-en-14-yl]-N-(2-methylpropyl)propanamide

• ChemBase ID: 154394
• Molecular Formular: C26H43NO2
• Molecular Mass: 401.62512
• Monoisotopic Mass: 401.32937962
• SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1C2=CC[C@@H]2[C@@]1(CC[C@@H](C2)O)C)C)C(=O)NCC(C)C
• Canonical SMILES: CC(CNC(=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2)O)C)C
• InChI: InChI=1S/C26H43NO2/c1-16(2)15-27-24(29)17(3)21-8-9-22-20-7-6-18-14-19(28)10-12-25(18,4)23(20)11-13-26(21,22)5/h7,16-19,21-23,28H,6,8-15H2,1-5H3,(H,27,29)/t17-,18-,19-,21+,22-,23-,25-,26+/m0/s1
• InChIKey: HUMXZYXRXDDZOG-LFZVSNMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(1R,2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-14-yl]-N-(2-methylpropyl)propanamide
• IUPAC Traditional name: (2S)-2-[(1R,2S,5S,7S,11R,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-14-yl]-N-(2-methylpropyl)propanamide
• Synonyms: (3S,20S)-20-N-(2-Methylpropyl)carbamoylpregn-7-en-3β-ol; (3S,20S)-3β-Hydroxy-N-(2-methylpropyl)-7-pregnene-20-carboxamide; Lathosterol Oxidase Inhibitor; Lathosterolamide MGI-39

Database IDs

• CAS Number: 1058719-76-8
• MDL Number: MFCD12912383
• PubChem SID: 162248533
• PubChem CID: 24801250

CALCULATED PROPERTIES

• Acid pKa: 16.121258
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 4.6442976
• LogD (pH = 7.4): 4.6443567
• Log P: 4.644357
• Molar Refractivity: 119.8183 cm^3
• Polarizability: 47.295906 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-50
• Safety Statements: 61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC)
• Quality Level: ELITE
• Empirical Formula (Hill Notation): C26H43NO2

DETAILS

Sigma Aldrich - 42129

Biochem/physiol Actions
Lathosterolamide MGI-39 is an inhibitor of lathosterol oxidase which converts 5-α-cholest-7-en-3-β-ol to cholesta-5,7-dien-3β-ol. 1