(4S)-4-[(2S)-2-[(2R,4S,5S)-5-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-4-hydroxy-2,7-dimethyloctanamido]propanamido]-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid

• ChemBase ID: 155627
• Molecular Formular: C41H64N8O14
• Molecular Mass: 892.99206
• Monoisotopic Mass: 892.45419877
• SMILES: C[C@H](C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)N)O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: CC(C[C@@H]([C@H](C[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)CCC(=O)O)C)C)O)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCC(=O)O)N)CC(=O)N)C
• InChI: InChI=1S/C41H64N8O14/c1-20(2)16-27(46-39(60)28(19-31(43)51)47-40(61)34(21(3)4)49-37(58)25(42)12-14-32(52)53)30(50)17-22(5)35(56)44-23(6)36(57)45-26(13-15-33(54)55)38(59)48-29(41(62)63)18-24-10-8-7-9-11-24/h7-11,20-23,25-30,34,50H,12-19,42H2,1-6H3,(H2,43,51)(H,44,56)(H,45,57)(H,46,60)(H,47,61)(H,48,59)(H,49,58)(H,52,53)(H,54,55)(H,62,63)/t22-,23+,25+,26+,27+,28+,29+,30+,34+/m1/s1
• InChIKey: NIOCOJFPGCXNKL-ZKZXETMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2R,4S,5S)-5-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-4-hydroxy-2,7-dimethyloctanamido]propanamido]-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2R,4S,5S)-5-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-methylbutanamido]-3-carbamoylpropanamido]-4-hydroxy-2,7-dimethyloctanamido]propanamido]-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid
• Synonyms: OM99-2; Glu-Val-Asn-[(2R,4S,5S)-5-amino-4-hydroxy-2,7-dimethyloctanoyl]-Ala-Glu-Phe

Database IDs

• CAS Number: 314266-76-7
• MDL Number: MFCD03452932
• PubChem SID: 162249765
• PubChem CID: 445649

CALCULATED PROPERTIES

• Acid pKa: 3.1863134
• H Acceptors: 15
• H Donor: 12
• LogD (pH = 5.5): -7.11699
• LogD (pH = 7.4): -10.511514
• Log P: -4.4654098
• Molar Refractivity: 220.9246 cm^3
• Polarizability: 87.28026 Å^3
• Polar Surface Area: 375.84 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >93% (HPLC)
• Empirical Formula (Hill Notation): C41H64N8O14

DETAILS

Sigma Aldrich - G8291

Amino Acid Sequence
Glu-Val-Asn-[(2R,4S,5S)-5-amino-4-hydroxy-2,7-dimethyloctanoyl]-Ala-Glu-Phe
Biochem/physiol Actions
Inhibitor of brain β-secretase