methyl (2S)-2-[(2S)-2-[(2S,3S)-2-[(3S,4S)-4-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-6-methylheptanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-6-{[(tert-butoxy)carbonyl]amino}hexanoate

• ChemBase ID: 132772
• Molecular Formular: C72H110N20O15
• Molecular Mass: 1495.7688
• Monoisotopic Mass: 1494.84595292
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)OC)NC(=O)C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc1ccccc1)O
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)OC)CCCCNC(=O)OC(C)(C)C)Cc1c[nH]cn1)NC(=O)C[C@@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CCCNC(=N)N)CCCNC(=N)N)Cc1ccccc1)Cc1c[nH]cn1)CC(C)C)O)C
• InChI: InChI=1S/C72H110N20O15/c1-9-44(4)59(65(100)89-55(36-48-39-78-42-83-48)62(97)85-51(67(102)105-8)25-16-17-29-81-70(103)107-72(5,6)7)91-58(94)37-57(93)52(33-43(2)3)86-63(98)54(35-47-38-77-41-82-47)87-61(96)53(34-45-21-12-10-13-22-45)88-64(99)56-28-20-32-92(56)66(101)50(27-19-31-80-69(75)76)84-60(95)49(26-18-30-79-68(73)74)90-71(104)106-40-46-23-14-11-15-24-46/h10-15,21-24,38-39,41-44,49-57,59,93H,9,16-20,25-37,40H2,1-8H3,(H,77,82)(H,78,83)(H,81,103)(H,84,95)(H,85,97)(H,86,98)(H,87,96)(H,88,99)(H,89,100)(H,90,104)(H,91,94)(H4,73,74,79)(H4,75,76,80)/t44-,49-,50-,51-,52-,53-,54-,55-,56-,57-,59-/m0/s1
• InChIKey: DLAHCJHYEAZDLE-VRYQDWSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-[(2S)-2-[(2S,3S)-2-[(3S,4S)-4-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-6-methylheptanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-6-{[(tert-butoxy)carbonyl]amino}hexanoate
• IUPAC Traditional name: methyl (2S)-2-[(2S)-2-[(2S,3S)-2-[(3S,4S)-4-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxy-6-methylheptanamido]-3-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-6-[(tert-butoxycarbonyl)amino]hexanoate
• Synonyms: CGP-29287; Z-Arg-Arg-Pro-Phe-His-Sta-Ile-His-Nε-Boc-Lys methyl ester

Database IDs

• CAS Number: 93287-54-8
• MDL Number: MFCD00133577
• PubChem SID: 162227049
• PubChem CID: 25078118

CALCULATED PROPERTIES

• Acid pKa: 11.831817
• H Acceptors: 20
• H Donor: 18
• LogD (pH = 5.5): -6.313024
• LogD (pH = 7.4): -4.8392887
• Log P: -0.45962945
• Molar Refractivity: 412.5195 cm^3
• Polarizability: 152.58484 Å^3
• Polar Surface Area: 528.36 Å^2
• Rotatable Bonds: 48
• Lipinski's Rule of Five: false

PROPERTIES

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: ≥85% (HPLC)

DETAILS

Sigma Aldrich - C9415

Biochem/physiol Actions
Primate-specific renin inhibitor with prolonged duration of action.